Are you tired of outdated, stereotypical, male-centered dating advice? Are you ready to embrace a more powerful approach to finding love? In this episode of the Financial Feminist, Tori sits down with Lily Womble, founder and CEO of Date Brazen and author of ‘Thank You, More Please,’ to discuss an intersectional approach to navigating the dating world. From breaking traditional dating norms to building self-trust and joy in your love life, this conversation offers invaluable insights for anyone looking to thrive in their relationships. Whether you’re single, dating, or in a relationship, Lily’s feminist approach to dating is designed to help you create a fulfilling and joyful love life on your own terms.
From matchmaker to feminist dating coach — Lily has more than a few years experience under her belt, and today she’s revealing the flaws in conventional dating advice and teaching you some practical strategies for in-person dating, and how to use dating apps with intention. If you’re ready to transform your dating experience and take control of your romantic destiny, this episode is a must-listen. Tune in to discover how to build a love life that truly reflects your desires and values.
Key takeaways:
- Build self-trust and practice compassion: Self-trust and compassion are foundational elements in feminist dating that help you recognize your own worth and make choices that honor your needs and desires. Lily emphasizes that self-trust involves acknowledging your needs and taking actionable steps to meet them. This might include simple daily actions, like recognizing when you need a break or support. Practicing self-compassion means treating yourself with the same kindness you would offer a friend, particularly when you make mistakes or feel down. This approach reduces stress and builds resilience, allowing you to approach dating with a strong sense of self.
- Critique conventional dating advice: Challenging outdated and simplistic dating advice is crucial for breaking free from patriarchal norms that limit women’s dating experiences. Lily argues that such advice can mislead people into thinking there’s a one-size-fits-all solution to dating. She also discusses how societal pressures, including those from patriarchal and capitalist structures, often push women to settle in relationships. By questioning and resisting these pressures, women can make more informed and empowering choices in their love lives
- Use dating apps with intention: Using dating apps mindfully can prevent burnout and help you find more meaningful connections, aligning with a feminist approach that values quality over quantity. Lily advises setting clear boundaries for dating app usage, such as limiting it to 20 minutes a day. This helps avoid the addictive nature of these apps and keeps you focused on meaningful interactions. She also recommends asking deeper, more qualifying questions to potential matches, which can help ensure your interactions are aligned with your values and desires.
- Engage in joy-building and social connections: Engaging in activities that bring joy and connecting with others in meaningful ways enhances overall well-being and expands your social network, making dating a more positive experience. One suggestion Lily gives is to make a list of 10 activities that bring you joy and commit to doing them regularly. This not only enriches your life but also creates opportunities to meet like-minded people. Additionally, leveraging “co-conspirators” or friends who understand and support your dating goals can help you find potential partners. These friends can introduce you to new people and provide moral support, making the dating process feel less isolating.
- Rewrite negative thoughts: Overcoming negative self-talk and societal conditioning is essential for building a healthy, feminist dating life where you recognize and embrace your own worth. Lily discusses the importance of addressing negative self-talk with self-compassion, using phrases like “It might be possible that…” to reframe your thoughts. This helps create new, positive neural pathways and challenges harmful beliefs about your worthiness. Understanding that feelings of unworthiness often stem from societal conditioning allows you to actively work on countering these beliefs, fostering a more empowered and positive self-image.
Notable quotes
“You can’t say the wrong thing to the right person.”
“Wanting what you want is revolutionary, and it’s breaking legacies of women who had to accept less.”
“‘[Saying] It happens when you least expect it’ vilifies people for having desires. Women’s desires challenge existing notions of power and order.”
Episode at-a-glance:
≫ 01:41 Introducing Lily Womble: Feminist dating coach
≫ 10:32 From advocacy to matchmaking
≫ 29:14 The patriarchal influence on dating
≫ 44:22 Understanding settling in relationships
≫ 48:20 The power of self-compassion
≫ 01:02:49 Navigating dating apps with intention
≫ 01:11:26 Building a joyful dating life
Lily’s Links:
Lily’s website: https://www.datebrazen.com/
Lily’s book: https://www.datebrazen.com/book
Special thanks to our sponsors:
Thrive Causemetics: Get an exclusive 10% off your first order at thrivecausemetics.com/FFPOD
Squarespace: Go to www.squarespace.com/FFPOD to save 10% off your first website or domain purchase.
Hill House: Visit hillhousehome.com and use the discount code TORI at check out for 15% off.
Indeed: Visit indeed.com/FFPOD to get a seventy-five dollar sponsored job credit to get your jobs more visibility.
RESOURCES:
Feeling Overwhelmed? Start here!
Our HYSA Partner Recommendation (terms apply)
Behind the Scenes and Extended Clips on Youtube
Leave Financial Feminist a Voicemail
Financial Feminist on Instagram
Take our FREE Money Personality Quiz
Meet Lily
Lily Womble is the Founder and CEO of Date Brazen, whose mission is to help badass, feminist humans build joyful, fulfilling, and confident-as-hell dating lives that lead to extraordinary love. Lily was raised in Birmingham, Alabama and being raised in the south, she saw that a woman’s worth was deeply tied to her romantic relationship status. A fierce feminist from a young age, Lily bucked against this convention and now as a feminist dating coach helps women center themselves (and not a romantic relationship) as the marker of their worth and power.
Lily began her career in the feminist advocacy and nonprofit space— from starting a nonprofit to end sex trafficking in Alabama, to working for an international women’s rights organization. This work took her to Istanbul, Yaoundé, Cameroon and Kuala Lumpur, but after finding herself burnt out from the first chapter of her career, took the leap to pursue another dream. In 2015, she moved to NYC to try a new career in musical theatre. During that time she worked various side hustle jobs and on a whim took another as a matchmaker (because if anything it would make for a good story). Turns out she was very good at it! During her matchmaking days, she set up 399 dates and became the 3rd most successful matchmaker out of 160 around the country. In setting up all these dates, she realized that dating is a microcosm of our overall wellbeing and working with women on their love lives really fit into her heart’s purpose.
Upon recognizing she was in a series of unfulfilling situationships, Lily realized that the answer to finding love was much deeper than a first date, and that the way we are taught to date is still stuck in the patriarchal dark ages. She started coaching with her unique approach, and it led to attracting her now-husband and her clients joyfully finding better dates for themselves than anyone else ever could. She broke up with matchmaking and founded her company, Date Brazen in 2018 and has since helped hundreds of women create love lives that are epic, settle-proof, and joyful-as-hell with her intersectional feminist approach.
After seeing the life changing impact of this work on her clients, she knew she wanted to write a book. In June 2022, Lily went viral on TikTok for a video called “Dating apps are a scam” which led to her book deal and The Date Brazen Podcast climbing to the top of the U.S. Relationship Charts. Her debut book, Thank You, More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love (Legacy Lit, 6/11/24) shares a proven guide to creating a confident and joyful dating life that makes the right relationship inevitable.
When she’s not running her six figure business, watching Gilmore Girls reruns or singing, Lily currently resides in New York City with her husband (a direct result of the Date Brazen way) and the love her life!
Transcript:
Lily Womble:
… we’re not taught how to even acknowledge what we want without it feeling threatening or feeling scary. And so even starting there, of giving yourself permission and learning your own essence-based preferences, and then asking for what you want the first time. That baby step work leads to massive freedom down the road.
Tori Dunlap:
Hello Financial Feminists. Welcome to the show. I’m a Stanley Cup girl. That’s the update, that’s the life update. I resisted it. I really did. I was like, they’re ridiculous. They’re too big. I just had my normal water bottle. I don’t need anything more than that. And then I was gifted my first Stanley Cup and I was like, “Let’s see what all the fuss is about.” And now we’re a fan. I have like three. I didn’t buy them. I just keep getting gifted them and I get it. I get it. I am hydrated. I’m carrying it around like a mom from New Jersey. I’m like, “I got to go pick the kicks up at like soccer practice, and Timmy’s sick again and I got to kick him up from school.” I don’t know, I’m doing a lot of picking up. That’s what happens when you have a mom from New Jersey with your Stanley Cup.
Okay, anyway, hello, welcome to the show. If you’re new here, welcome. My name is Tori. I teach you how to be good with money and fight the patriarchy by getting you rich, which is pretty cool. This show talks about how money affects women differently, but really a lot of the things that affect women differently. And if you’re an oldie but a goodie, you already knew that.
If you’re wondering where to get started on your money journey, well first of all, you’re in a great place just listening to this show. We have over 150 episodes for you to go listen to about everything in anything personal finance, but also feminism. And you can take our six step quiz to get a free personalized money plan at herfirst100k.com/quiz. We’ll also link it down below.
Today’s guest is a fun one because first of all, we’ve never done a dating episode on this show, but second of all, it happens a lot where I’ve realized that the guest and I have a lot of the same interests and are basically the same person.
Lily Womble is the founder and CEO of Date Brazen, whose mission is to help badass feminist humans build joyful, fulfilling, and confident as hell dating lives that lead to extraordinary love. A fierce feminist from a young age, Lily bucked against this convention, and now as a feminist dating coach helps women center themselves, and not a romantic relationship, as the marker of their worth and power. Hell, yeah. Lily began her career in the feminist advocacy and nonprofit space, from starting a nonprofit to end sex trafficking in Alabama, to working for an international women’s rights organization.
In 2015, she moved to New York City to try a new career in musical theater. Are you starting to see where she and I might be similar? During that time, she worked various side hustle jobs and on a whim took another as a matchmaker because if anything, it would make a good story. After a series of unfulfilling situationships Lily realized that the answer to finding love was much deeper than a first date, and that the way we are taught to date is still stuck in the patriarchal dark ages. She broke up with matchmaking and founded her company Date Brazen in 2018 and has since helped hundreds of women create love lives that are epic, subtle proof and joyful as hell with her intersectional feminist approach.
Her debut book, Thank You, More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, shares a proven guide to creating a confident and joyful dating life that makes the right relationship inevitable. We’re talking today about dating, duh, of course, but specifically why dating hasn’t really progressed in a way that’s made it better for anyone, not just women. What it means to date like a feminist. Why traditional dating advice is mostly trash. Why Lily and myself don’t like the phrase, “if they wanted to, they would”. And why lily thinks dating apps aren’t really built for people looking for relationships.
So if you are someone who is doing the swiping thing, who is struggling to meet people, is maybe out of a relationship for the first time and trying to figure out what’s going on. This is a perfect episode. It’s also a great episode to send to your single friends who are feeling like, “Oh my God, maybe something’s wrong with me because…” Hint, it’s not you, babe, it’s not you. It’s the patriarchal shit. Without further ado, let’s go ahead and get into it. But first a word from our sponsors.
Do you have a background in musical theater? Is that what we found out when-
Lily Womble:
Yes.
Tori Dunlap:
… Okay. So I majored in theater in college.
Lily Womble:
Musical theater or straight plays?
Tori Dunlap:
Straight theater. We did some, it wasn’t a big enough program to support both, but I grew up doing both. But I love musicals, but I was trained more in straight theater.
Lily Womble:
Okay, got it. I feel that it helps us in our careers now.
Tori Dunlap:
Oh, the amount of people who were like, “What are you going to do with a theater degree?” I’m like, “I don’t know, make a lot of money. Show up on a podcast. Do fine.”
Lily Womble:
Be the most polished podcast you’ve ever seen in your whole life.
Tori Dunlap:
So, fucking, fucking polished. Yes. No, but I think that’s one thing that I wish more people talked about. It’s like, “What are you going to do with those liberal arts degree?” And I’m like, “Basically anything. Anything you want.”
Lily Womble:
Yeah, live my life well. I don’t know.
Tori Dunlap:
I know. What’s your favorite musical? I know. Pick your favorite child.
Lily Womble:
Chorus Line. Oh, Chorus Line.
Tori Dunlap:
Okay.
Lily Womble:
Yeah. Like, “[inaudible 00:05:17] 10, looks, 3 and I’m still on unemployment.”
Tori Dunlap:
Oh yeah, I went through a big tits and ass phase.
Lily Womble:
Look, as a child, I was like, “Oh my God, this is the funniest thing I’ve ever heard in my life.”
Tori Dunlap:
Same thing. And I was like, “Wow, this is so scandalous.” And it was on my iPod and my parents didn’t know it.
Lily Womble:
Well, and then when I became a Gilmore Girls fan, which then is a huge other part of my personality, I also learned about the Emily Gilmore, which is obviously… What’s her name? I’m blanking on her actual name.
Tori Dunlap:
Kelly?
Lily Womble:
Kelly Bishop.
Tori Dunlap:
Yep.
Lily Womble:
Was in the original cast, and that’s her story of my dad cheated on my mom, and my mom found the mistress’s panties in the back of her car. That’s her life story in the play.
Tori Dunlap:
I don’t know if I knew that. That’s fucking wild. Okay, so I’m a big girl Gilmore Girls fan too. I grew up on Gilmore Girls. I feel like if I could point to anything and be like, “That determined my personality.” It was the dialogue of Gilmore Girls.
Lily Womble:
Which part Tori? Oh, the dialogue. The rat-a-tat.
Tori Dunlap:
Just the references. Yeah. I mean, if you read my book, it’s a personal finance book, but I just drop references to things. And literally the copy editor was like, “You need to explain this.” And I’m like, “No, we’re playing by Gilmore Girls rules. If you don’t get the reference, you either need to Google it or you got to move on.”
Lily Womble:
You can’t play. Yeah, for sure. Oh, I think that that’s brilliant. I think I over explained my references, but I did feel that I had as many as I wanted. It was like Parks and Rec, Ocean’s 11-
Tori Dunlap:
Yep. What? We’re the same person. I’m sorry. Okay. First of all, Ocean’s 11, and anybody who knows me knows this, I watch that movie every six weeks. Every six weeks.
Lily Womble:
I’ve seen the movie 50 times. Quote Danny Ocean. Because I think that the dating world is like the… I call it the dating casino, because it’s so loud, it’s a labyrinth built to keep you trapped in. And so that begins chapter one, is the Danny Ocean… Anyway, we have a lot in common. We must take this offline.
Tori Dunlap:
“Does he make you laugh?” “He doesn’t make me want to cry.”
Lily Womble:
Wow. Wow. Let’s take a moment for that Julia Roberts. I did have a moment in the book that was taken out. That was like Julia Roberts is the most stunning damsel in distress in the whole movie. The only woman who has lines, literally the only woman who has lines in the entire film.
Tori Dunlap:
I joke, the feminism leaves my body, James Bond in Ocean’s 11. I’m sorry, I didn’t need an Ocean’s 8. I’m good. I’m good. Keep the bros, I’m good. Keep the Rusty.
Lily Womble:
Wow, hot take. Hot take.
Tori Dunlap:
I know it’s a hot take. I know. And then James Bond, I’m like, “I don’t need character arcs. I don’t need you being a father. I need you being a daddy, and I need you to…” It’s the most controversial opinion I have, which is like, I need you out here having casual sex. Shoot big guns.
Lily Womble:
Cate Blanchett was so hot though.
Tori Dunlap:
Oh, of course.
Lily Womble:
She was so hot in Ocean’s 8. Oh, my God-
Tori Dunlap:
No, I think Ocean’s 8 was a great movie and it was fantastic-
Lily Womble:
You can’t backtrack now.
Tori Dunlap:
… and I just jokingly say-
Lily Womble:
No, you can’t. No, go ahead.
Tori Dunlap:
… Okay. All right. I just say, I love Ocean’s 11. I think it’s the perfect movie. No notes. Absolutely none. I love that movie. It is the comfort of all comfort movies, and I love that movie so much.
Lily Womble:
Agree. [inaudible 00:08:27].
Tori Dunlap:
I listened to the soundtrack writing my book. I had a playlist and it was the majority. It was just Ocean’s 11 soundtrack. That’s the only reason the book got done.
Lily Womble:
Mine was The Holiday.
Tori Dunlap:
Oh.
Lily Womble:
The Holiday was on repeat, like, “Da-da-da-da”
Tori Dunlap:
Da-da-da-da.
Lily Womble:
I was like, “Yes.”
Tori Dunlap:
Yep, yep. I get that. I went through a Nancy Meyers kick earlier this year, because I hadn’t seen The Holiday until last year. I know.
Lily Womble:
Wow.
Tori Dunlap:
I know.
Lily Womble:
You were behind on that. But that’s okay.
Tori Dunlap:
But I grew up with… Parent Trap was my favorite. I loved Nancy Meyer’s Parent Trap, and then Father the Bride and Father the Bride II were like Dunlap family movies. Yeah. Okay. I know we have other things to talk about. I can stay here… Oh. What team are we on, on Gilmore Girls?
Lily Womble:
I literally ran the Gilmore Girls Fan Fest debate on this topic in Kent, Connecticut.
Tori Dunlap:
Okay. I’m talking about how we’re basically the same person. This will determine whether we’re the same person or not.
Lily Womble:
Okay. Well, I think that there’s no perfect choice. Just because-
Tori Dunlap:
Sure.
Lily Womble:
… That I shouldn’t have to be pigeonholed to choose, is my feminist answer. Because Rory needs to come into her own. Jess. Are you a Logan?
Tori Dunlap:
Nope, I’m a Jess.
Lily Womble:
Oh, you’re a Jess. Okay.
Tori Dunlap:
I am all the way. I am so Jess Mariano. I did do a re-watch recently. I didn’t hate Logan as much as I did. I remember growing up and I hated Logan.
Lily Womble:
Yeah, yeah, yeah. Well, he’s super hot. But when Jess comes in with those Distiller tickets at 10 P.M., coming in late, hasn’t planned a date. When he’s deciding whether or not to smoke that cigarette, I’m like, “Oh, my God.”
Tori Dunlap:
“Why did you drop out of Yale?”
Lily Womble:
Oh, my God.
Tori Dunlap:
No, I’m sorry. And also Milo Ventimiglia has been my celebrity crush forever. No, Team Jess. Sorry. Team Jess all the way.
Lily Womble:
Oh my God.
Tori Dunlap:
All the way.
Lily Womble:
Well, in our other podcast, Feminist Deep Dive on Gilmore Girls, we dive into all that. So tune in listeners.
Tori Dunlap:
I love it. Okay. Happy to have you on the show. This is so fun. Yes, it makes me so happy. Okay, so you went from working in advocacy and nonprofit, to then chasing your musical theater dreams, to becoming a matchmaker, and now you’re a feminist dating coach. So tell me everything. How did that happen?
Lily Womble:
Well, let’s do the abridged version.
Tori Dunlap:
Sure.
Lily Womble:
So my heart was always performing in high school, middle school, high school. Performance and advocacy. So I was out there starting a nonprofit in high school for survivors of sex trafficking in Alabama, and going to Montgomery and advocating for legislation, of which the state of Alabama at that time didn’t have any legislation around human trafficking, they were relying only on the federal law. So I was very much foot in two camps, advocacy and also performance. And when I didn’t get into my dream musical theater school, which was Elon at the time, I thought, “Okay, this is my redirection. I’m going to go all in on international relations.” And got to dive into the world of nonprofit advocacy in the U.S., which is a deeply flawed place because of the way capitalism has screwed up how we care for one another.
So nonprofit world, if you are listening and you work for a nonprofit, God bless you. It is such tough work. Not paid enough. It is very difficult. So when I burnt out of that world after a couple of years inside of it, I was like, “Oh, maybe this is my redirection back to my dream of performance.” And so no friends, no money, quit my job, moved to New York, found a job at a church where I could live there in exchange for my rent, iconic, in Hell’s Kitchen. And I had 50 side hustles. I was a nanny, I was a receptionist. I also was a balloon hat maker at Senor Frogs in Times Square. I could make a penis hat coming into a pair of lips, as a hat. I can text you the picture after.
Tori Dunlap:
Wow. Do you still have that skill? Is that under special skills on your resume?
Lily Womble:
Well, thank God I run my own business. I don’t need a resume anymore. However-
Tori Dunlap:
No, sorry, on your theater resume.
Lily Womble:
… it would’ve been.
Tori Dunlap:
Yeah, that would have been-
Lily Womble:
Oh, at the time?
Tori Dunlap:
… yeah, special skills. Yeah.
Lily Womble:
Oh, 100%. At the time. Yes, yes. I thought you were talking about today. I definitely can. I could go make a quick buck on the corner shilling some balloon hats, and I’m so grateful I don’t need to anymore. So I needed another side hustle because I didn’t have much money at all. I remember I was so poor at the time for me, I know that I held a ton of privilege living where I did, doing what I did. But I remember putting the tiny $1 bill tips that I got, at the Bank of America, they were all tattered and ripped, and sliding them into the slot and praying that they weren’t ripped enough to not go through.
Anyway, I heard through the grapevine that a matchmaking company was hiring. And I, as a late bloomer who didn’t have much romantic experience outside of my high school boyfriend who dumped me, telling me that I was “too much”, I thought, “LOL, how hilarious that I’m applying to be a matchmaker. LOL, that’s hilarious.” Didn’t have any intentions of being in the dating space, didn’t have any intentions of making this my career. However, I got the job. It was sink or swim, not much training, and I learned that I was really good at it. I was really good at getting beneath the surface of what people wanted, and asking deeper questions. My EQ was off the charts. And I started setting up matches. Meanwhile, I was in the worst toxic relationship of my life. I had settled so hard for this guy I met on Bumble. What are you thinking, Tori? I see your face. And I’m just so curious.
Tori Dunlap:
Oh, I mean, you’re describing my life. But keep going. You’re doing great.
Lily Womble:
Okay. Okay. Okay. Well, that’s the thing that’s great about this book is that there are so many, all of us who are feminists who are taught that we were too much growing up. All of this is why I have a job now because this is so relatable.
So I was in this relationship with this guy who wanted to be with me, and I thought that was enough. And I also fell in love with him. And I also was like, “Oh, I’m too much, so nobody else is going to want to be with me, so I’ve got to make this work.” Meanwhile, my parents were getting a divorce at the same time, and I just grew up seeing how much work women around me were having to do in their romantic relationships to make them work. And so I thought, well, that’s just normal. And I was miserable, and I would cry on his bathroom floor and then five minutes later take a matchmaking client call saying, “You deserve so much more. Let’s get you out on some great dates.”
And it was so painful to be in that place. And the cognitive dissonance was astounding. And at that point, I had started therapy, and thank God, because she really helped me build the skills to break it off with this person who ultimately was the worst fit. And when I found the courage to leave that relationship I looked around… And I had gotten really good at matchmaking. I became the third most successful out of 160 at that national firm. But I saw that matchmaking was this first date level solution. And while it was working for some people, I knew that I wanted something much deeper than a first date. I didn’t trust myself to never settle again. I was like, “How do I never settle again?”
My therapist hadn’t dated in 30 years. Besides helping me break up with that person and build some deep skills to maybe trust myself more, she didn’t know what to tell me with dating. Then I looked to my friends and family who were like, “Why don’t you just swipe more? Why don’t we make over your dating profile? Why don’t you just get on the other app?” That’s the dating casino, the loud advice from everybody around you who’s found love, who randomly landed in a relationship telling you what you should do. And I was like, “That’s not going to work.”
I also had professionally swiped on all the dating apps, so I knew their dating bullshit, and I knew that dating apps were not the answer. So I started becoming my own first client. I started uncovering the, “you’re too much” belief and started learning the skill of self-compassion. I started uncovering my own preferences, beneath the surface of my checklist that got me in that good-on-paper-bad-relationship before. And I found out what essence I was looking for. And I started building skills to be more playful, and messy, and self-trusting in my dating life. And that led to me flirtily giving my number to waiters, and having more fun, and feeling free in my dating life, which then ultimately led me to meet the love of my life IRL, who I may not have said yes or swiped yes to him had I not done this deeper work on my own preferences. So I was like, “Oo, this is working.”
And I went to my matchmaking clients and I started coaching them with these same tools, like secretly, and they started to find better dates for themselves than I or anybody else could find for them. And so about seven years ago, I broke up with matchmaking and I started my company Date Brazen, to be the feminist answer to, “How do I make dating feel better? How do I actually make it joyful? How can I meet the right partner on my terms without settling or compromising?”
And I’ve since gotten to coach hundreds of people around the world with these tools, and have written the book on the subject called Thank You, More Please, which came out on June 11th. And I’m so, so proud of it and I know it’s going to change people’s whole fucking lives.
Tori Dunlap:
And thank you all for coming. Appreciate you. That was great. No, I plus a thousand to all of that. Oh my God, you said so many things. We have other questions and I want to get into them, but what you said, I think that is so important. So I met my now partner IRL as well. I met him at a bar, sat down next to him. After dating apps for years and years and years, and had some success and some not so success on the dating apps. And I was the very similar person where everybody was like, “You’ll find somebody eventually.” And, “Here’s all of the advice.” And, “Oh, I’ll introduce you to this person…” And it was just like, “Okay.”
And honestly, what you said, I’m trying to remember what exactly it was you said, but it sparked something of what I had to realize in my own life about dating, which is I had so much expectation for what the relationship should be. I grew up Catholic. It was like, no, you date to find the relationship.
Lily Womble:
Right, right.
Tori Dunlap:
And anything that you immediately realize this person’s not interested in a relationship, don’t waste your time on that. And I actually went through, my previous partner before I met my current one, we both knew going in that this probably wasn’t going to last, but I fell madly in love with this person. It was one of the most incredible experiences of my entire life. Also devastating when it ended. But I was so glad it happened because it allowed me to realize that I would put too much weight too early on something. And then I also would just put blinders on of like, “Okay, if you don’t also want a relationship…”
As soon as I let go of expectations, I had my fun little, the whole phase where I was just out just giving my number to random men on the subway, going and putting my Hinge location in London just to feel fun and flirty. And it was just like there was no expectations. Did that for a while, actually had fun with it, and then met my partner just because I wasn’t… I don’t know it worked for me to not have all of the, “I need to find the relationship and the one.” And just be like, “You know what? I’m just going to have some fun for a while.” I don’t know.
Lily Womble:
Tori, can I break down what you did?
Tori Dunlap:
Yeah, talk to me.
Lily Womble:
Can I break it down? Because it’s what I talk about in chapter seven, which is dating in-person with main character energy. Main character energy is a skill set. It’s not like Tori has it and you don’t. It’s not like I have it and you don’t. It is a teachable, learnable, practicable skill set that is three things that you did in so much, line in heaps.
Gave yourself permission. You gave yourself permission to do whatever the fuck you wanted, want what you wanted, have more fun, play around, get kind of messy. Love that.
Self-trust. You trusted yourself, that, “I’m going to try shit and it’s going to be okay.” Why? “Because I have my own back,” I would imagine.
Tori Dunlap:
Yeah.
Lily Womble:
And then the third step of main character energy is massive messy action. And so main character energy is what leads to successful IRL dating, successful dating, successful life, I think, fulfilling life. But I just wanted to mention you did exactly what I hope everybody does, which is those three things, permission, self-trust, and massive messy action.
Tori Dunlap:
No, I love that. Yeah. It felt so serious for me. And then as soon as I let go of the seriousness of it and was just like, “Let’s try to find kind people who I have chemistry with, who I don’t have to see the next 10 years together. We can just see where things are going.” And even in my relationship, normal, I shouldn’t say even normal Tori, early Tori would’ve been like, “Okay, we’re going to lock this down after five dates and we’re going to get in a relationship.”
We dated for six months until we had the official, “We’re dating no one else,” conversation. And I did that on purpose so that I wasn’t putting all of my eggs in this basket too early, before the basket had… I don’t know, this metaphor doesn’t work. But before the basket had been fully weaved, I didn’t want all of the eggs in it.
Lily Womble:
Yeah, I love that.
Tori Dunlap:
Anyway. Yeah, I love asking people out publicly. It’s so fun. So many women feel embarrassed by it. I think it’s exhilarating. It feels like you’re getting on a roller coaster. I don’t know. I love it. I think it’s fun. And just not having expectations for me is what really unlocked a lot of stuff.
Lily Womble:
I think that’s so powerful. And I think that the skill that people need to embody to be able to ask people out in-person is the skill of shame resilience. It sounds so not sexy, but it sounds like, because you love that thrill, it sounds like you have a really high shame resilience set of skills. Because people fear rejection like they fear death because when we lived in caves rejection did mean death. And so people fear making the first move, or asking somebody out IRL, but if you have the skill of, I’m willing to feel anything to be with you, with yourself, that self compassion that neutralizes the feeling of shame, or helps it pass faster, then you become unstoppable. Like literally unstoppable in your love life and everywhere.
Tori Dunlap:
I had to hype myself up every time, let’s be real. The knees weak, arms sweaty, that was it every time. But it was like I had to pep talk myself and say, “Okay, if they say, ‘No’, fine. Your hearts going to hammer for the next five minutes after, and that’s okay. What’s the worst they can say? ‘No, I am dating somebody already,’ or, ‘No, I’m not interested.’ Great. Okay.”
And I wouldn’t do it for the other person. I would do it for me. I would do it for the confidence it gave me. My outcome or success was not in their answer, success was I did it. And it was like, cool.
Lily Womble:
That’s so good. Well, and that’s like what’s in your control, which you’re reframing. You were reframing to what’s in your control, instead of what I hear so many people doing, which is, “I’ve never been asked out in-person, so that means people must not like me. So that means I probably shouldn’t try because people have already told me that they don’t like me.” Instead of reframing to, “What if I was in control of my own experience and my own interpretation of these scenarios, and literally it doesn’t matter. Let’s go be messy, and playful, and try things.” If you’re willing to feel awkward, you become unstoppable.
Tori Dunlap:
I love my partner and my partner loves me, but we’ve had a conversation after. I did the, “Hey, hand me your phone,” after we were done talking and typed my number in. And I go, “Would you have asked me?” And he goes, “Probably not.” And I’m like, “Okay.”
Lily Womble:
Interesting. Interesting.
Tori Dunlap:
He was like, “I hadn’t been on a date in two and a half years. I was not looking for numbers. I didn’t want to assume.” And I’m like, “Okay, so this might not have happened had I not been the one to be like, ‘Give me your phone. I’ll type in my number and we can text.'”
Lily Womble:
Okay, this is why I hate the “if he wanted to, he would” advice. I hate it.
Tori Dunlap:
Ugh, me too. Sometimes they can’t, sometimes they don’t have the capacity. Oh, I-
Lily Womble:
Or sometimes they’re just distracted and doing something else and you saying one thing pivots their attention, or pivots… And I think that the reasoning behind that advice, it’s very similar to the decenter men conversation, which I think is important to have for a lot of reasons. Both…and I think that unnecessary emotional labor has been heaved upon women and people socialized as women in all scenarios. And so I think the intention of “if he wanted to, he would”, the intention of that advice is to, I think originally, unload some of that emotional labor.
Both…and I also think that it comes from this place of, “Prove to me that you’re interested,” which is putting the relationship already out on kind of an unequal footing, putting a lot of weight on their response, their behavior. And instead, I do think that it’s about decentering the people who are wrong for you. Instead of saying like, “Oh, well that person did that and he broke up with me and so I shouldn’t try again.” Decenter the people who were wrong for you, and then focus on co-creation. Co-creation is what you did at the bar. You had a conversation, you gave your number, and your now partner probably came back with questions, thoughts, conversation. It wasn’t all on you. The emotional labor wasn’t all on you. So it’s not just, “if he wanted to he would,” it’s a co-creation of two human beings.
Tori Dunlap:
Yeah. I gave him my number and then whether he texted me or not, that was up to him.
Lily Womble:
But a relationship wouldn’t have started if he hadn’t come back with something. So it is that equal effort that comes in, that I think “if he wanted to he would” leaves out of the equation.
Tori Dunlap:
My other big issue with, “if he wanted to he would” just implies the Disney prince. I literally was watching Bridgerton just before I jumped on with you-
Lily Womble:
The new Part Two.
Tori Dunlap:
Uh-huh.
Lily Womble:
Don’t say anything.
Tori Dunlap:
I won’t.
Lily Womble:
Okay.
Tori Dunlap:
But the romance version of what we’re told as women, especially if you’re dating men or interested in men, is it’s the like, “Well, if he wanted to he would. He’d do all of these things and he’d know exactly what to say.” And it’s like, “No, that’s completely unreasonable.”
If I expect to be loved a certain way, I need to tell you that that is my expectation and give you the handbook. Now, if you throw away the handbook that’s on you, if you choose not to consult the handbook, that’s on you, but it’s not on you to read my mind about what I want. So I think a lot of social media is like, “if he wanted to he would”. Really, to them it means, “Well, he should just know that this is how I want to be loved or how I want to receive affection.” And it’s like, “No, every single person’s different.”
Lily Womble:
Right, right. Well, and in my experience with Chris, my now husband, he asked me out, I wasn’t ready, I was still healing from that relationship that ended and I said, “No.” I was like, “Hey, I can’t.” He wanted to text and be cute, kind of get to know each other over text, and I literally said, “I can’t talk to you. I know you have a crush on me. I think you’re cute, but I can’t talk to you.” And I set that boundary and we didn’t talk. We just hung out in a group twice after that, in the next couple of months. And then once I felt like, “Oh, shit, this man is someone that I want to get to know more and I feel that it’s right now.” I asked him out. And he responded like, “Yes.” And so I do think that it’s that co-creation, not muscling, not doing all of the emotional labor. It’s that co-creation.
Tori Dunlap:
Okay. I’ve not asked you any of the questions on here. So okay, you’ve shared that the way we date is in the patriarchal dark ages. What are some of the glaring examples of that?
Lily Womble:
Telling women, and people socialized as women, that they’re being too picky? Picky is just pick with a Y at the end. Literally vilifying people for having agency in their desires.
Tori Dunlap:
Standards.
Lily Womble:
Yeah, standards. So I do think that there’s people who might go toward rigidity in order to self-protect. That’s not what I’m talking about with picky. Picky is wanting what you want.
Another example is the settling pressure. I grew up in the deep south where I saw that a woman’s worth was deeply tied to her relationship status with a cisgender man. And so I saw that single women were treated as literal, less than human beings, because they weren’t coupled.
And imagine what that implicit and explicit pressure does to our nervous systems over time. Imagine what that does to our brains over time. That implicit and explicit pressure. The pressure from your mom at the holidays. Getting the tiny, shitty, single, twin blow up mattress on the floor while your married sister takes the bedroom. Think about the level of pressure that single women are under all the time to be coupled up, in order to be more desirable to people around them, more worthy, or whole, or what the fuck ever. And to get conspiratorial for a second, let’s go there, Tori.
Tori Dunlap:
Yeah.
Lily Womble:
If we think about the declining birth rate in our country and world, which I don’t have an opinion on… What the fuck, like I don’t know. But I do know that because of the declining birth rate, it is in the best interest of people from the top to pressure folks, specifically women, specifically people who can birth humans, to settle down pretty quickly and make babies.
Tori Dunlap:
And immediately start pumping them out.
Lily Womble:
So we can have more labor for the workforce. So if we think about top down, where is this pressure coming from? It’s not just coming from the church. I was raised evangelical Christian, forget about it. You know what I’m saying? It’s coming from all of these different places, which is why dating advice, I think, so often focuses on helping women settle. Instead of helping women, and people socialized as women, thrive in their love lives. Thrive and settle proof every inch of their lives. Want more. Because wanting what you want is revolutionary, and it’s breaking legacies of women who had to accept less.
If we think about this year was the 50th anniversary of when a woman could get a credit card without her husband’s permission. So it’s not very recent that women didn’t have to settle in a marriage, whether or not it was a good marriage, settle for economic security and potentially freedom. So that’s how the dating world is still stuck in the patriarchal dark ages, and why I wrote my book, and why I started my company, and why I get to help people settle proof their love lives every single day, and learn how to take up more space. Because this shit is deeper than just dating.
Tori Dunlap:
That’s why I love doing this show, because everything you just said is everything we talk about here, and everything I discussed in my work, and it’s not a conspiracy… It’s not a-
Lily Womble:
Conspiratorial.
Tori Dunlap:
… It’s so true. No, because I talk about it all the time, money is as a form of control. Money is power, and we want to talk about… Yeah, I quote that stat in my book. 1974 was the first year a woman could have a credit card in her own name. A business loan I think came eight to 10 years after that. It was the ’80s.
So it’s like, yeah, marriage was a financial decision more than anything else. That’s why we had dowries and sometimes still do. It’s not been about and about healthy relationships, it’s been totally patriarchal, all of it.
Lily Womble:
Yeah. Yeah.
Tori Dunlap:
Yep. Okay. So are you noticing this patriarchal influence across the spectrum for both, obviously hetero relationships, but also queer relationships too? Or is it mostly just women who date men?
Lily Womble:
Yeah, so for self-disclosure purposes, I am with a cisgender man in a straight presenting relationship. I’m queer. I’m bi. I didn’t have a ton of lived experience dating women because I came out and shortly after met Chris, and we’re monogamous. So I like to share all of that information to share that I do have a lot of queer clients, and I do think that the patriarchy fucks us all up.
And I do think that for men, the patriarchy has fucked up men too. Toxic masculinity has impacted their ability to ask for emotional support, or connect with loved ones or friends, and that impacts their wellbeing and their ability to be in healthy relationships too.
So I think that across the board, yes, there are expectations. Talking specifically about queer women and femmes that I’ve worked with, expectations that they place on themselves to perform a certain way, to care-give at a certain level, to emotionally burden themselves. Like queer women and straight women alike, emotionally burden themselves with most of the emotional labor in a relationship because of how they were taught to survive as people-pleasers. In order to belong in their family units, in order to belong at work potentially. So, absolutely. Yeah, 100%.
Tori Dunlap:
Yeah. I mean, patriarchy fucks us all up, and we’ve said that many times in this show too. And regardless of your gender identity.
Lily Womble:
Yeah, the intersectionality of it all also is something that I really wanted to honor in the book. That patriarchy, white supremacy, homophobia, transphobia is all working together in a hot soup of awful, to create a dating world that is difficult for everyone. Especially people who hold marginalized identities, especially people of color, women of color, Black women. It is hard. And that’s why I have a job. Because we’re not taught how to advocate for our own needs, we’re not taught how to even acknowledge what we want without it feeling threatening or feeling scary. And so even starting there, of giving yourself permission and learning your own essence-based preferences, and then asking for what you want the first time, that baby step work leads to massive freedom down the road.
Tori Dunlap:
You’ve mentioned already in our conversation, but I know a lot of your book is about this feeling of self-trust for women, or getting to a point where women do trust themselves. I know from literally talking with the millions of people in our community, talking with other women friends. It’s not that we don’t want to trust ourselves, it’s that patriarchy and the systems that exist they’ve gaslit us into not trusting our own intuition, and not respecting our own needs, and not even being able to hear sometimes our own intuition because everything’s just too loud. So what does building self-trust look like in a practical way? How can women specifically build self-trust and how can we build self-trust when it comes to dating?
Lily Womble:
Yeah, so self-trust is… I mean, after my terrible toxic relationship, didn’t trust myself at all. I was like, I thought I trusted myself then, when I got in that relationship. I thought I had self-trust. So I think that it’s important. I talk to so many people who’ve been in bad relationships and they say the same things. And I think it’s important, right now, whoever’s listening, to stop using your relationship history as a weapon against yourself moving forward.
Yes, I made decisions that I wouldn’t make again. Yes, you might’ve made decisions that you wouldn’t make again. Both…and how about that’s humanity. How about it’s okay to learn something new. And so I think just first base level that, it’s okay to messily, imperfectly, learn something new. And self-trust is a skill, that is a practicable, learnable skill. And I quote Brené Brown in the book, from Daring Greatly, talking about how trust with other people is built in marbles, like tiny marbles added to a jar. And self-trust is the same thing. It’s tiny choices. Choice by choice, moment by moment.
One of my clients the other day asked the same question, “Practically how?” And I was like, “Just for one day, listen to yourself and go to the bathroom exactly when you feel the desire to.” Literally that tiny step can be like, “Okay, instead of waiting for that meeting to pass, where I’m crossing my legs because I have to pee so fucking bad, why don’t I actually pause my Zoom, say, ‘I need to step away for a moment and I’m going to go use the restroom.'”
Tori Dunlap:
The amount of times I’m like, “Okay, you get to go to the bathroom when you finish this email.” It’s like earned. We have to earn a little pee.
Lily Womble:
I know. Well, there it is, right? The idea that we have to earn-
Tori Dunlap:
Ludicrous. Crazy. Yep.
Lily Womble:
… Which is those moments where we think that we owe our computer something, or that it proves something about us that we’re going to hold our pee-
Tori Dunlap:
Self-control.
Lily Womble:
… for another hour to get more work out for… The self-control, right? But what’s happening in the conversation about self-control is a fundamental lack of self-compassion. Because if we just looked at ourselves as soft, squishy human beings who need things sometimes.
Using the pee example, if I go to the bathroom exactly… I went to the bathroom five minutes before this recording. I do it before every meeting because it’s part of my Type A personality, number one. Number two, it’s a gift that I’m giving to myself to listen to my body and to trust my body’s instincts. And then in this scenario, if you’re trying to learn self-trust, you could say, “Hey, Lily, I trusted myself just then. Good job.” Acknowledging it.
That’s what the Thank You, More Please is about, the title of my book, it’s like, “Thank you, more please. Thank you moment where I listen to myself. More please.” And it can go for external things too, like seeing a cutie exiting a therapy office. Thank you, more please. Having a flirty conversation with your barista. Thank you, more please. To build evidence that what you want exists. Same with building evidence that I can build self-trust. You’ve got to notice the small steps.
And then in terms of dating, I really recommend people do a date feedback system, that I teach inside of the book. Where after the date, I have a spreadsheet that all of my clients use, and it’s not about being super rigid, it’s about noticing. Because what’s happening after dates is your hormones are raging, you have a lot of feelings, and you probably won’t remember the details. And so putting down on a piece of paper, “What questions did they ask me? What made me come alive in the conversation? What’s my most beautiful and true next step?”, allows you to start building self-trust after dates, by tuning in with your dating intuition. So I think it’s about those small baby steps. It’s about the small tiles that make up the mosaic of self-trust.
Tori Dunlap:
Yeah. What you said at the beginning too, a lot of people, which is very sweet, ask me, “I want to be confident like you. How did you get to be confident?” Because I made fucking stupid mistakes that I would not make now. And I do not blame myself at all. I look back at younger me and I was like, “She was doing the best she could with the information she had.” That was it.
And our audience knows, because I’ve told this story a lot, my first serious boyfriend, who I thought I was going to marry, once told me I was fat on a beach because his mom told him that she thought I’d be skinnier, the first time she met me. And I remember feeling so ashamed and angry. And I was 20 years old. I was so distraught and angry, and I should have honored myself then and taken myself home. We were in Hawaii. I was away from home. I should have gotten on the next plane, I should have come home, but I didn’t.
And I still have a choice. I could look back at twenty-year-old me and be like, “You stupid, fucking bitch. You should have just got on that plane. It was horrible, and you stayed in that relationship for another two years.” And instead I’m like, “You know what? I get why she did it. She felt lost. She didn’t have the money to get herself back on a plane. She loved him and didn’t understand it. And had to figure out why and had to understand…” And it’s just like the only reason I have standards now is because they were violated at some point. And then I realized, “I don’t like that, so I’m not going to let it happen again.”
Lily Womble:
Yeah, I have so many of those moments too, Tori. Literally one of them is in my book, of I was in this bad relationship, we were in love, we went to Paris a couple of months into our relationship. And the first night in Paris, I was like, “I’m living my dream.” All of this is on a credit card. I have no money. I am so excited to be living my Passport to Paris fantasy. And we’ve decided to be monogamous. We’ve made a commitment to each other. First adult relationship, first time having sex, all of these things with him. He looks at me and he’s like, “Lily, I actually realized that I need to be in an open relationship for this to work, and I can’t be in a monogamous relationship.” And for those listening, I don’t hate non-monogamy. If it’s right for you, then it’s right for you.
Tori Dunlap:
No, that’s fine. But not in mother-fucking Paris. Paris, Helen? Paris?
Lily Womble:
Not after I put 5K onto my credit card for this trip with this man that I was in love with. And so in that moment, I think back, and I wish that I had looked at him and really listened to my body and discerned, “Actually, if something feels like your body is on fire from the inside out, it’s actually wrong for you, Lily. And so you don’t have to say, ‘Yes’.”-
Tori Dunlap:
Stay.
Lily Womble:
… And I wish I’d stood up and had a little solo Paris trip, but instead I stayed for a year.
Tori Dunlap:
Yep, yep, yep.
Lily Womble:
So I totally get that, and I felt regret over that moment, and other moments in my journey. Both…and in my more compassionate moments, I can say what you just said, which is like I did literally the best I could based on what I knew at the time, and that doesn’t mean that I’m not trustworthy now.
Tori Dunlap:
No, and I learned sometimes you realize what your boundaries are because they get crossed and you go, “Actually, that didn’t feel good. So that is a boundary.” Or, “I’m not going to have that happen again.”
And again, talking about my handbook before, I have told this story to every partner I’ve dated, and in the future, and not like any of them would, but I’m like, “I don’t want comments about my body unless they’re nothing but positive. And anything even close to that is going to be triggering for me because of this experience that happened in the past.” So yeah, you’ve just learned what treatment you will or won’t accept, because sometimes you accepted it and hated it.
Lily Womble:
Yeah, yeah.
Tori Dunlap:
Yeah. Oh, boy. Anyway. Got to love that. You’ve got to love that story. Okay. This quote from your book, “If the patriarchy is interested in keeping power in the hands of the powerful, then it’s in its best interest for women to settle.”
Okay, so speaking of stupid boyfriends, what does settling look like for your clients and how can we fucking stop settling in our lives?
Lily Womble:
Yeah. Settling looks like a couple different things. Settling can look like before you ever meet somebody. Settling for a shitty feeling dating life is a version of settling. Dating is a microcosm of our well-being. It’s every hope, joy, dream, fear, insecurity, desire that we have as humans. You owe it to yourself and your nervous system to figure out how to pursue your desire more joyfully. Not because of anybody else, but just for yourself. Dating gets to be an active agency, and joy, and power. So don’t small settle for a shitty feeling dating life, that has 15 dating apps and a ton of dates, playing the numbers game. Or maybe you’re settling by not trying at all. Like under-functioning by saying, “I don’t need anything.” When actually you have a desire. It’s okay.
I think there’s a myth wafting around some feminist circles that says, “Wanting a relationship makes you weak, or pathetic, or makes you less of a feminist.” And I do think that it’s about acknowledging your desire and saying like, “Yeah, I believe you. It’s okay. It’s okay to want what you want.” It’s a both…and. I’m a feminist and I want the right partner. Not, “I’m either a feminist and I don’t need anybody,” or, “I want a partner, and I am a tradwife.” It’s like, “No, I get to want what I want.” Yeah?
Another version of settling is, the good enough, good on paper. “I don’t know what’s wrong, but I don’t feel good in this relationship, but I guess that’s okay because it’s normal.” No, the right relationship should feel supportive and easeful, and you get to feel how you want to feel. You get to feel held, and seen, and validated, and supported. That exists. And if you haven’t seen that what you want exists, then it’s time to do a Thank You, More Please challenge in your own life, and in the world, of looking for moments where you have felt that way with a partner or a friend. You have felt seen, held. Say, “Thank you, more please. Okay, it does exist. It might exist more if I keep looking for it more.”
Tori Dunlap:
I have a theory about that. We’ve talked about the, I call it the head hit your pillow at night before you go to bed, and you’re like, “Something’s not right.” But you stay. I think we as human beings, especially your example of the caveman, which I bring up all the time too, it’s comfortable. It’s comfortable. It’s not risky. It doesn’t make you feel good. It doesn’t make you feel happy, but big scary world out there. It’s easier to stay in something that you might not like but you know what it is, then go out there to big scary world that is a berry bush that you haven’t eaten before and is a cave that could get you killed. So I’m going to stay in my cave. I’m going to eat from this one berry bush that I know isn’t poisonous. I don’t love my life, but it’s too scary to think of other things.
And couple that with, I think, the feeling of unworthiness. This is fine. I’m not worthy of more than this. I not worthy of a partner who loves me in this way. I’m not worthy of the job. I’m not worthy of this, because other people can have that, it’s not for me though. So I feel like it’s that comfort. It’s that homeostasis, where we get comfortable in our lives. And I don’t mean safe, I mean just doing the same thing over and over and over again. Not happy, but also because we don’t believe we’re worthy of anything more than that.
Lily Womble:
Can I say something that feels like a hot take?
Tori Dunlap:
Sure. We love hot takes.
Lily Womble:
I am going to say this, and then I’m going to back it up with a lot of thoughts that are going to make you feel amazing, but first it’s going to be like, “Huh?”. You’re not special. Okay? If you say to me, “I’m uniquely unqualified, I’m uniquely broken. I’m uniquely the one who doesn’t get what she wants. I’m the one who can’t seem to figure it out, and it’s not going to be possible, so I better just hole up in my house with five cats, and that’s totally fine. But I’m afraid of cats. I’m afraid they’re going to eat me.” And I want you to go outside and experience life and have the…
I’ve seen so many people, so many people who have worked with me, who’ve listened to my free podcast, who have read my book, who have felt that way. Who have felt like, “I’m uniquely bad at this. I’m uniquely unqualified. I’m uniquely unworthy.” Who all they needed was community with people who got what they were going through, and self-compassion, and some action steps. Literally, that’s all you need to start getting more of what you want.
And if you don’t believe me, then you can borrow some of my belief. I’ve seen hundreds of people get in the best fucking relationships of their lives. And create not only that… Because I think the relationship is the bonus. I think the winning results, the thing that we’re in control of is how you live your best freaking life possible, and how you take up more space in this world, and then other bonus results flow from that work. Like getting bigger promotions, making more money, going on more epic trips, moving to the place you’ve always wanted to-
Tori Dunlap:
Like yourself more.
Lily Womble:
… Liking yourself more, having more fucking amazing sex. All of these are the bonus results of trusting yourself enough to pursue your desire, and learning those things of trust, permission, and massive messy action.
Tori Dunlap:
I’ve heard it phrased as, “How egotistical is that? To be like, ‘I am the problem. It’s me. Everything’s wrong with me. I’m not special. I’m not worthy.'” And I’m like-
Lily Womble:
Well, it can be very easy to think that in your love life if you’re the only single friend in your friend group and everybody else is married.
Tori Dunlap:
… Very valid.
Lily Womble:
So that’s why… Yeah.
Tori Dunlap:
No, but I’m echoing what you said of, yeah, this feeling of, “I’m not special, I can’t do it.” And I’m like, it’s actually weirdly egotistical.
Lily Womble:
Yes.
Tori Dunlap:
It’s like, “I don’t deserve love.” Why do you not deserve love, bitch? I’m sorry, why are you, of all people? You believe everybody else deserves love? Why do you believe that you can’t and don’t get it?
Lily Womble:
Because of patriarchal conditioning.
Tori Dunlap:
Of course.
We get it. We get it.
Lily Womble:
Of course. It all drains lead to the ocean that is patriarchy.
Tori Dunlap:
Well, I think, yeah-
Lily Womble:
Yeah, but especially if you’re the only single friend. That’s rough.
… And that’s why all of my programs are group coaching programs. That’s why we do this in community, because community and belonging is inherently subtle proofing. Because when you see that you’re not alone and other people are doing this with you, and that you’re not weird for wanting something, or weird for trying, you do more epic shit.
So I think that. And then if you’re struggling, and you’re like, “It’s me, I am the problem. This is me they’re talking about,” then I think a baby step could be just doing a simple Thank You, More Please challenge. What do you want, and how can you go out in the world this week and look for tiny, tiny slivers of evidence that what you want exists, that you might be exactly who somebody would want to be with? And say, “Thank you, more please,” to every sliver of evidence. To build that active bank of evidence that what you want exists and it is possible for you.
Tori Dunlap:
A lot of what you’re talking about is how we’re speaking to ourselves, which I really, really appreciate. How do we start redirecting the thought that is like, “Oh, I’m out at this bar and no one’s asked me out, therefore, I’m unlovable.”? How do we stop that or anything like that? “Oh, I am swiping on the apps and everybody’s a piece of shit today, so it must be me.” How do we redirect that and start rewriting that script in our head?
Lily Womble:
Great question. The way that we don’t do that is with toxic positivity. So I see most people who want to reframe, or rephrase, or whatever in their [inaudible 00:52:48] brain say like, “No, it is possible. No, you’re wrong. Shut up brain.” I call that the thought seesaw. On one hand, you have, “I’m not attractive. Nobody wants to be with me.” And on the other hand, you have, “Yes, I am. Yes, they will.” It’s the aggressive opposite that I think we’re taught helps, but it’s sort of like putting a new coat of paint over a wall that is crumbling. Toxic positivity is like a cheap plastic bandaid, it’ll fall off the minute you’re in hot water.
And so the way that you actively, in an evidence-based way, reframe that thought is by acknowledging that it’s a thought, not a fact, first. Acknowledge it. Like it’s a sentence in my brain, “Hey, thought. Okay. Hey, thought.” Using the bar example, like okay, nobody’s come up to us and we’re having the thought. That means that it’s not possible and that nobody wants to be with us. Okay, we’re having that thought.
Then self-compassion. Self-compassion isn’t just a fluffy phrase, it is a proven resource, in a 2014 study out of Stanford, that found that self-compassion reduces cortisol and increases resilience. Two things that you definitely need to do, anything epic and attract, anything that you want in this life. Self-compassion in that moment in the bar could sound like, “Gosh, it really sucks to feel this way. I’m here for you. Of course you feel this way. Of course, you want somebody to approach you. That sounds really normal and understandable. And I also hear you’re having hard thoughts like, ‘Ugh.’ I’m here for you.”
Then once your nervous system, you’ve allowed it to reset, you can then go to a baby step new thought that uses the starter phrase, “It might be possible that… It might be true that…” So it might be possible that it would feel really good to go up to somebody right now and say, hello. It might be possible that this isn’t my night, and that’s okay. Not every night has to be the hottest night of my life. It might be possible that I haven’t met everyone. It might be possible that someone’s here that I could make eye contact with. It might be possible that this is just the beginning. It might be possible…
Literally those three steps. Which is acknowledging thoughts not facts, practicing self-compassion, and doing baby step reframe in the moment, to be like, “It might be possible that…” But you got to start with the nervous system care first. All of that with practice might only take two minutes. It’s not going to be that deep, but you got to start practicing.
Because the neural pathway, “It’s not possible,” it’s like a well-worn path. And building a new neural pathway is like being in the middle of the jungle with a machete, and somebody drops you in the middle and is like, “Build a new path.” And you’re like, “What? I’m scared I don’t know where to go.” And your brain’s like, “Yeah, we’re building a new path. It takes practice, it takes effort. It takes coming back.” That’s why when you go on paths that have been so well trodden over millions of steps, they look like roads because they’ve been well trodden. You’ve got to start practicing a new baby step thought to build that neural pathway.
Tori Dunlap:
You all can’t see me. My head hurts and neck hurts from shaking my head too much. No, okay, so what you just said, Lily, because I know my listeners. And they’re doing the thing in their head where they’re like, “Okay, yeah. The little like, ‘Okay, everything’s going to be fine.’ And the baby talk in your head that’s like…”
I do this all the time. It feels so bizarre. The first time you do it, you feel like you’re talking to a child and it feels, at first, a little condescending. Where you’re like, “It’s okay. I’m really sorry this is happening to you.” And you’re like, “I’m a big girl, I don’t need that. I don’t need to do that.” You fucking do. I do this with myself all the time.
Well, it’s just like the self compassion and the acknowledgement, it really helps me, and I’ve talked about this on the show before, is I will journal as two different versions of myself when I’m not doing well-
Lily Womble:
Love that.
Tori Dunlap:
… Is I will do the, “I’m really, really scared and I’m really stressed out.” “Honey, what’s going on?” The one I think of all the time was like, “I went to the doctor and the doctor’s worried that everything’s wrong with me, and I think I have cancer and also a brain tumor and I’m going to die.” “That sounds really scary, but I’m going to be here with you, and I’m not going to leave you, and everything’s going to be okay.”
And even that, it sounds so ridiculous when you hear somebody talk about it, until you do it. And then you realize, oh, this actually helps.
Lily Womble:
Yeah, and just to pull the curtain back on why self-compassion might feel cheesy or even intolerable for most people. Let me lean closer to the mic. It’s because most of our parents didn’t know how to help us have and move through big feelings.
Using an example of a teacher. You remember when you’re on a playground and a friend rejects you, says, “You can’t play with us.” And it hurts and you’re crying. And there are two teachers. The first teacher comes over and is like, “What happened? Tell me what happened. Why are you crying?”
Tori Dunlap:
“What’s going on?”
Lily Womble:
“Okay, what’s going on? Okay, that doesn’t sound that bad. Okay. It’s okay. Brush it off, brush it off. Go back and play. You’ll feel better if you just go back.”
Tori Dunlap:
As Taylor Tomlinson’s dad says, “Eat some peanut butter. You’ll feel better.” Have you seen her sketch about this?
Lily Womble:
No, but that’s very true.
Tori Dunlap:
She basically in high school goes to her dad and she’s like, “Dad, I think I’m depressed.” And he’s like, “You need some protein. Eat some peanut butter.”
Lily Womble:
Oh my God. Oh my God.
Tori Dunlap:
But didn’t a lot of our parents do that?
Lily Womble:
I know, they-
Tori Dunlap:
My mom, bless her, I’ll call her and be like, “I’m not doing well today.” She’s like, “Have you pooped? Have you gone on a walk? Go on a walk.”
Lily Womble:
… Oh my God, yes.
Go a walk. Everything will be okay.
Tori Dunlap:
Well, it’s that nobody teaches this vocabulary of how to effectively care for our feelings and move through them.
And the fixing it. I want to fix it. My mom wants her baby’s pain to go away. I get it, but I’m not calling you, Mom, for a solution, I’m calling you so that you can hear me, that I’m really stressed and upset.
Lily Womble:
And the only way through that pain is through it. Right?
Tori Dunlap:
Yeah.
Lily Womble:
So let’s think about the other teacher, the teacher who comes over to you when you’re crying on the playground, and gets down on your level and says like, “Hey, tell me what’s going on.” And then you as a kid are like, “Oh, she just rejected me. She made me feel so sad and called me names.” And you might cry more for a second because of the acknowledgement of this moment. But the teacher’s like, “Oh, that really is so painful. I’m sorry. And is there anything else?” And you’re like, “Oh, I guess something else, something else, something else.” And then the teacher says, “That’s really hard. Do you want to hug?” The teacher gives you a hug, and the vibe of the hug is, “I’ll be here as long as you need me to be.”
What happens then? Inevitably, you will feel better quicker because of the acknowledgement and the care, and the, “I’ll be here as long as you need me to be,” vibe. And you’ll hear somebody playing off in the background and you’ll want to get out there faster, more authentically. And you’ll say, “Hey, I’m going to go play.” And she’ll be like, “Are you sure I’m here for you?” “No, I’m ready. I’m ready to go play. Thank you. Bye.”
You want to be that second teacher to yourself, that second version of re-parenting that is more caring and getting on your level, so that you can go play faster.
Tori Dunlap:
That’s so brilliant, Lily. That’s so smart. You’re exactly right. That’s so good. I love it.
Okay, I’ve seen this on social media. Sorry, I’ve read in a research paper, I saw a TikTok video, and you say it too, which is basically you can’t do the wrong thing to the wrong person.
Lily Womble:
You can’t say the wrong thing to the right person.
Tori Dunlap:
Yes. Sorry. Thank you. You can’t say the wrong thing to the right person. Yes.
Lily Womble:
Yes. And to my knowledge, I was the first video that went viral on that.
Tori Dunlap:
Oh, I love it. Cool.
Lily Womble:
Yes.
Tori Dunlap:
Okay, so I’m talking to the OG. Okay, great.
Lily Womble:
I think. I think. In so far as I know. You know, on social media, whatever. But I’m pretty confident.
Tori Dunlap:
And I love that I’m talking to you because I literally brought this up with somebody yesterday, and I’m like, “The very things about dating that people find disgusting with the wrong person, are the very things that they find so great.” Of like, “Oh my God, he texts me every morning and he says, ‘Good morning, beautiful.’ And he calls me every day and he wants to know what I’m doing.”
And the flip side of that is like, “Oh my God, he texts me every fucking day, and he texts me right when I get up in the morning.” And I’m just like, “This is fucking too much.” It’s the exact same thing, but whether we’re into somebody or we’re not into somebody.
Lily Womble:
Yeah. So, “you can’t say the wrong thing to the right person” was born from my first date with Chris, where I definitely did something that I would not recommend. Which is, I talked about my ex for 30 minutes, Tori.
Tori Dunlap:
Oh, girl.
Lily Womble:
Not great. Not great. Not great.
Tori Dunlap:
I love that matchmaker broke cardinal rule of dating, which is never bring up ex.
Lily Womble:
Oh my God. Well, by this point… Oh, no, I was still a matchmaker, wasn’t I? Oh my God. That was like seven years ago now, so it’s like, yep, that was about the time I was breaking up with matchmaking. But I was on the date, and when I talked about my ex, it was from a question of, “How are you doing?” And then I just went on this verbal processing thing and he made me feel safe. He made me feel seen. He held my hands when they were cold, out in the cold November air, and warmed me up. He was so kind and he made me feel how I wanted to feel. He was meeting those essence-based preferences. And that’s how I know you can’t say the wrong thing to the right person, we’ve been together seven years.
Now, the additional piece to that is that a couple of months in Chris was able to say to me, I was still talking about my ex sometimes, not sometimes, often, he was like, “Hey, I would love it if we could talk about us and you could process with your therapist or your friends. I love you, I care about you, but can you talk about that with somebody else? Because I don’t really want to talk about your ex anymore.”
And the right person will also be able to set boundaries with you. They’ll be an adult who can communicate. And so it is, you can’t say the wrong thing to the right person, and you are uniquely qualified for the right person because that person will know how to advocate for themselves too.
Tori Dunlap:
Yes. Yes, yes, yes. Yep. Yep. Just can’t… I’m just going to move on because it’s yes.
You’re not a fan of dating apps. Tell me more about that.
Lily Womble:
My first viral video was, Dating apps are a scam. So I think that with any publicly traded company, or any company that is held within a publicly traded company, we’ve got to keep our eyes wide open. You know what I’m saying? So dating apps have this reputation, I would say less so this year with all of the attention on how they are impacting our brains and how they’re addictive. And I’ve been having this conversation for seven years, but I think people are awakening to that conversation differently than they have in the past few years before this.
So dating apps have these multimillion, maybe billion dollar marketing budgets over the last 12 years, that have influenced how we think about dating and how we think about dating apps. For example, Hinge is designed to be deleted. This marketing message creates this expectation, or this feeling, of like, “Oh, they’ve got my back. Oh, they want me to delete them.” It’s a great marketing message, but if we think about what’s actually happening, it’s a publicly traded company that wants more users, to generate more revenue for their shareholders.
And I don’t think business is inherently a bad thing. However, if we think about the dating app’s main objective. Hinge Tinder, Match.com, a lot of them are owned by Match Group. Bumble obviously is a separate thing. It’s a publicly traded company all on its own. Their job is to get more users and keep users on. And that’s why I think that from anecdotal evidence, and from my own experience, and from the data from my clients and people that I’ve spoken with over this last seven years, dating apps are giving you enough of the good stuff to keep you coming back. But they’re not essentially solving the problem that they promise to. Which is, Hinge is designed to be deleted. They actually don’t want to be deleted. They want to give you enough of the good stuff to keep you coming back, but not enough to keep you full.
That’s why I liken them to McDonald’s fries. McDonald’s fries are delicious, they’re salty, and they’re covered in a type of sugar called dextrose. So they don’t fill you up, they just keep you wanting to have more. And so that’s why I don’t think dating apps are the enemy of one’s dating life, but I think that most people are using them and they’re being taken advantage of. Their nervous systems, their brains are being taken of by the addictive features. Because dating apps are built like slot machines designed to keep you gamified in the system.
And so coming in with an intentional plan, with boundaries, with a clear profile that asks for exactly what you want, using one dating app 20 minutes a day, that way you can be the CEO of that resource. And dating apps are optional when you have a badass in-person dating life. And that’s what I think we need to talk about more. Social skills have eroded over the last four plus years, for obvious reasons. And so how can I help people build up the confidence and social skills necessary to start shooting their shot more, to start joy-building more, making new friendships, helping their friends more effectively, help set them up? I call that the co-conspirator strategy. I talk about it in chapter seven.
But that’s why I think dating apps can be really harmful to our wellbeing, and why I think you need a plan, and why you need to come in with eyes wide open, and also why I think in-person dating is so necessary.
Tori Dunlap:
Oh, so many thoughts about what you just said. Yeah, I mean, I am willing to admit this, I’m not proud of it, I very much love my partner, I love our relationship, and I sometimes will be like, “You know what? That amount of attention all the time was kind of nice.” And I hated the apps, don’t get me wrong, but also I had men telling me I was pretty all the time, and it’s very addicting. It’s very addicting.
Lily Womble:
Yep, yep. Our brains love to see faces. We have these mirror neurons that are firing off. That’s why in this conversation that I’ve mirrored you in body language. We want to see faces and we want to connect with other human beings. But similar to TikTok, which is I’m so grateful to TikTok in some ways. It’s-
Tori Dunlap:
Right. [inaudible 01:07:12] Same girl. Gosh.
Lily Womble:
… difficult for my mental health in a lot of other ways.
Tori Dunlap:
Yep. Same.
Lily Womble:
That app doesn’t want you to set boundaries with it. No.
Tori Dunlap:
No. That’s why it doesn’t stop scrolling. I couldn’t believe I hadn’t thought of that. Somebody said that a year ago on, I think it was a podcast, and I heard it and was like, “Oh, yeah, it never stops.” You don’t get to the end of TikTok. You don’t get to the end of Instagram. It’s not like a book where you shut it and you’re like, “Okay, I’m done.” There’s no end. Ever. You don’t run out of TikToks to watch.
Lily Womble:
Yeah. So I do think that it’s important to acknowledge how your brain might be addicted to the faces, addicted to the matches of the messages. And then reframe to like, “Okay, what’s my core desire? What’s my why for being on this resource?” And then, “How can I really make a plan of intention around my why?” Instead of searching for the…
Because look, if you look to a dating app to prove to you that what you want is possible, you will consistently be burnt out, exhausted and overwhelmed. It’s like trying to look to TikTok comments to make me feel better as a human being. It’s never going to work. Because there’s going to be one positive one and there’s going to be one that rips me apart. And so I can’t look to that for my validation. I have to do a deeper dive into what’s my why and how do I want to navigate this with agency? Same, same with dating apps.
Tori Dunlap:
Okay, so I’m putting myself in the listener’s shoes. I even know as me, the fact that I met my partner at a bar, I know, at least it feels statistically unlikely. It’s also, I was not supposed to be at that bar at that time. He was not supposed to be at the bar. I had never been to that bar before. We weren’t supposed to be sitting there. There were many things where I’m like, “It was fate.” But I can hear somebody listening to this and being like, “Okay, but the apps feel like a necessary evil. You’re telling me, Lily, to go and date in-person. Where am I finding people? What am I doing? What is the script? Where am I going? How do I get brave enough to…? Tell me.”
Lily Womble:
Yes, okay. So first caveat, I don’t think that dating apps should be thrown out in the trash completely. I think that you got to use them with intention and power-
Tori Dunlap:
Right. You said 20 minutes a day. I think that’s great.
Lily Womble:
… Yeah, and especially for queer folks, trans folks, it can literally be unsafe to date in-person. And so I do think that issuing that caveat of, it may be that if you want to date, you got to be on a dating app. However, you need to take the power back from that resource by setting your own boundaries, by asking deeper questions when you open conversations. My favorite one is, “What’s bringing you joy lately?”
Okay, in terms of in…
Tori Dunlap:
Lily, you and are the same God damn person. My opening on every dating app was, “Hi person. What are you most excited about in your life right now?” That was my opening line.
Lily Womble:
That’s it.
Tori Dunlap:
And then I still have some screenshots that are like, “Your tits.” And I’m like, of course-
Lily Womble:
Bye. Bless and release.
Tori Dunlap:
… Truly, bye. I’m like, “You’re not wrong. But also, goodbye.”
Lily Womble:
Yes.
Tori Dunlap:
No, you and I are the God damn same person. Okay, sorry, keep going. That’s so funny.
Lily Womble:
Well, I call them qualifying/disqualifying questions, and you were doing that naturally. I did that naturally. I teach it now. In my book there’s literally 50 qualifying/disqualifying questions, organized by preference. On what questions you could ask in a conversation to gauge whether or not somebody has your essence-based preferences.
Tori Dunlap:
Okay, I have to ask, let’s say we’re just down to fuck, what’s the question I’m asking?
Lily Womble:
You just want to hook up?
Tori Dunlap:
Yeah. What’s the question I’m asking somebody.
Lily Womble:
Oh, well, you could just open with like, “Hey-
Tori Dunlap:
Want to fuck?
Lily Womble:
… I’m looking for a great time. Want to hang out tonight?” Or something like, “You want to hook up tonight?” You could just do that. You could also, a couple messages into the conversation, be like, “You’re really cute. Want to hang out tonight?” Make it simple. But don’t make it super complicated.
Tori Dunlap:
I didn’t know if the qualifying question was… Okay, let’s keep going.
Lily Womble:
The QD questions depends on what you want, right?
Tori Dunlap:
Right.
Lily Womble:
So if you’re looking for a serious relationship, if you’re looking for a hookup, you might ask different things. If you’re looking for a hookup that feels more serious, that feels more connected or emotional, you might ask different questions.
So let’s talk about IRL dating though now, because I have a three-step system that I’m so proud of, and I’ve taught hundreds of my clients and it’s so good.
Three steps. Number one, joy-building. This is just to increase the quality of your fucking life. Make a list of 10 things that you want to do this month that sound joyful. Food festivals, meetup groups, pottery classes, dance classes, whatever. I don’t care if someone is at the class that you’re attracted to. I don’t care. That’s not the point. The point is going to do something that brings you joy, to increase the quality of your life, and to make connections with new people.
Because your job at the joy-building activity is to make eye contact with new people, to say hello, and to strike up a conversation. That way you are expanding your social circle, which in fact is the function, the only function of a dating app that is within your control, is expanding your social circle. So you can do that organically IRL with joy-building.
Now, then you get to Step Two, which is co-conspiratorship. Co-conspirators. This is how you tap your friends to help you better.
Are you saying, this is me? Tori-
Tori Dunlap:
My friend-
Lily Womble:
… your facial expressions. I can’t stop.
Tori Dunlap:
… I know. I’m sorry, I keep derailing. No, but my friend Kelsey was my wing woman the night I met my partner and was talking me up. She’s like, “Can I show him your Instagram?” And I’m like, “Yeah, that’s fine.” And she’s like, “Look at this girl. Look at what she does for a living. She’s an author. She’s a this.” And he was just like, “Oh my God.” He’s like, “This is you?” And I’m like, “Yeah, it’s me. No big deal.”
Lily Womble:
Amazing.
Tori Dunlap:
But literally was wing-womaning me all night. I went to the bathroom. Apparently she talked me up the entire time I was in the bathroom.
Lily Womble:
Oh my God, she’s the best co-conspirator. I love this.
Tori Dunlap:
And she was not drinking. She played designated driver. Oh, she gets Friend the Century Award. So, yeah, co-conspirators.
Lily Womble:
I love it. Yeah, so for some people, their friends say problematic stuff about their dating lives, or their friends just are like, “I don’t know how to help you.” Or, “I don’t know any single people.” And so the co-conspirator strategy is about identifying one or two people who you’re really close to, who you know want to love you better. And bringing your essence-based preferences, which is a whole process that I teach in the book of identifying how you want to feel in the right relationship, and coming up with your own root words that have your own definition, that are a clear picture of the kind of relationship that you want to be in. It’s not a rigid checklist. It’s not an open-minded pile of mush. It’s how you want to feel.
So you bring your essence-based preferences. You bring your qualifying/disqualifying questions to your co-conspirator. You say, “Hey, I would like to come up with creative solutions together for my dating life. Here’s what I’m looking for. Can we go out once a month, or once a week, to a bar and you be my wing person? Here’s what that would look like ideally. Could you look out for me at your next work conference or when you’re in the airport?”
Two of my clients were co-conspirators for each other. They lived in different states, and one of them was in the airport for work of the other client’s city, met a guy, asked him the questions, for the QD questions gauged the essence-based preferences, asked if he was single, set them up and they started dating. That’s what I’m talking about with co-conspiratorship, helping your friends help you shoot your shot.
Now, I also in the book have a list of “Oh-no-nos.” Tom Haverford’s list of “Oh-no-nos” was from the show Parks and Recreation. One of them was, “If she doesn’t like 90s R&B music, then it’s a oh-no-no.” Oh-no-nos for your co-conspirators are when they say things like, “I just don’t know anybody single. Maybe you’re being too picky. Maybe you should just move, there’s nobody in our city.” I literally script out responses for you to say to your elected co-conspirator to help them love you better, and help get them on the co-conspirator track.
And so it’s about joy-building. It’s about co-conspiratorship, and then the third and final is about messy eye contact. This is where you got to believe that if I’m willing to feel awkward, then I become unstoppable. I have a whole in-person dating Bingo card in the book at the end of chapter eight, where I list out, in a Bingo card, that I want you… I was like, “Publisher, I need this page to be blank on the other side so people can rip it out and put it on their fridge.” It has literal action steps, like make eye contact with three cute humans, then check off the little box in your Bingo card. And take yourself on a luxurious date. Practice a self-compassion meditation. Ask someone out on a date. Bless and release someone. If you follow those Bingo steps, you will have a robust, badass in-person dating life.
Tori Dunlap:
I fucking love it. That’s so great.
Lily Womble:
Yay.
Tori Dunlap:
Okay, everybody. Everybody, you’re listening. You’re going to rewind about eight minutes and you’re going to listen to the whole thing again, and then you’re going to go out and do it. And you’re going to buy her book and it’s going to be great.
Okay, I have to wrap up, even though I could talk to you for the next three hours. What’s the worst dating advice you’ve ever heard? What’s the advice that you hear and you’re just like, “No, absolutely not.”
Lily Womble:
“It happens when you least expect it.” No, no, no. Oh-no-no. Oh- no-no. It’s like vilifying people, specifically women for having desires. Which again, that’s about women’s desires make people uncomfortable because they challenge existing notions of power and order. And it’s important for you, because your friends who are saying this to you, “It happens to the least expect it,” they might have settled, unfortunately, I wish the best for all coupled people everywhere, but they might have settled. They might have not have known their own preferences. They may not have known how to advocate for themselves. You know what I’m saying?
So I think that it’s important to look at who’s giving this advice and bless and release their opinion of what’s necessary to find your incredible partnership. Because your path is your own, and wanting something is exactly what will help you attract it. Similar to if you were like, “I’m looking for a job, but I don’t want to be too much, and I don’t want to be too specific. So I don’t know, any job where they pay me a good salary and people are nice.” You’re going to end up in the worst job that you’ve ever heard of.
Tori Dunlap:
Or no job, because you’re not specific enough for people to understand what you actually want.
Lily Womble:
And that’s the, “it happens when you least expect it”, sort of advice. And then whereas if you had your essence-based preferences, if you had your qualifying/disqualification questions for a job scenario, that would be, “I know what the culture is like at the company. I know what salary range I’m going for. I know exactly what bonus package I want and deserve. I know exactly what I want leadership to focus on, and how I want them to treat their employees with dignity and respect every single day. And here’s what that looks like.” You’re so much more likely to find the best fucking job of your life because of those skills, and because of that vocabulary, and because of your knowledge of your own desire. Same-same with your love life.
Tori Dunlap:
I will admit, I have probably said that to people. And what I mean by it is, it’s like I have, again, back to my original point, and this will tie us up perfectly, I think I put blinders on about what I wanted. And I probably wouldn’t have talked to my partner if I wasn’t open to understanding, “Oh, it did happen when I least expected it.” But because I put myself in a position to start talking to people, and be open, and to do all of those things. That was not the plan. So that’s probably how I’ve interpreted it. But I agree, it’s often, “it happens when you least expect it because I’ve settled.”
Lily Womble:
One of my friends, and this is what I finished the book with, this quote, one of my friends said something that I find to be a more helpful alternative to that phrase. When I was in the depths of despair about my love life, I felt like I was too much. I felt so ashamed and sad. And she was on the phone with me and she was like A), “I’m so sorry you’re feeling this way. This really sucks. I’ve been where you are. I feel you. I’m so sorry you’re struggling.” So A). Validation. I’m just breaking down the mechanics of this incredibly helpful statement. B), “I don’t know when it’s going to happen Lily, but I have confidence that the right relationship is coming.” And so that’s B). Acknowledgement of it’s coming. C), “I will believe it for you until you can believe it for yourself.” And that’s what I wrote in the final chapter of the book, is to everyone listening and reading, I will believe it for you until you can believe it for yourself.
Tori Dunlap:
Oh, sorry. That’s so lovely. That’s so lovely. That’s what you want.
Lily Womble:
Yeah.
Tori Dunlap:
You want somebody to believe it for you until you believe for yourself.
Lily Womble:
Yeah.
Tori Dunlap:
Yeah, that’s great. Go buy her book everybody. Thank you for being here. Plug away. Your book, your work. Go for it.
Lily Womble:
Yes. Oh, thank you, Tori. I am so excited for anybody listening to pick up a copy of my new book. Thank you, More Please. I’m going to say my desire, my desire is to be a bestseller. And I would love to get this book in as many hands as possible. And so, Thank You, More Please. A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, is out anywhere books are sold, and you can go pick up your copy.
I also did the audiobook and it’s really fucking good. So the ebook is out there as well. You can learn how to work with me at my website, datebrazen.com, and you can listen to all of the 200 plus episodes of the Date Brazen podcast anywhere you listen to podcasts. And I’m also on Instagram and TikTok, @datebrazen.
Tori Dunlap:
Thank you. Thank you for your work. I’m so excited. Everybody go read the book. I’m going to go read it. I’m in a happy relationship and I’m still going to go read the book.
Lily Womble:
Amazing. Thank you, Tori.
Tori Dunlap:
Thank you so much to Lily for joining us. You can buy her book. Thank you, More Please, wherever you get your books. I got a copy. It’s great. It’s fantastic. Again, great for you if you are dating, if you are single, but also just great for anybody just trying to stand more in their power and figure out love and what they want. If you’re someone in a relationship that is maybe going through a hard time, another good one to read too. So again, Thank you, More Please, wherever you get your books.
Thank you as always for being here financial feminists. We appreciate you all. You can leave us a review if you like the show, and if you don’t like the show, stop listening. Go listen to something you like. I don’t want you wasting your time with something that you hate. Go do something you like instead.
Okay. Hope you’re having a good summer. Okay. Bye.
Thank you for listening to Financial Feminist, a Her First $100K podcast. Financial Feminist is hosted by me, Tori Dunlap, produced by Kristen Fields and Tamisha Grant. Research by Sarah Sciortino. Audio and Video Engineering by Alyssa Midcalf. Marketing and Operations by Karina Patel and Amanda Leffew.
Special thanks to our team at Her First $100K, Kailyn, Sprinkle, Masha Bakhmetyeva, Taylor Chou, Sasha Bonar, Rae Wong, Elizabeth McCumber, Claire Kurronen, Daryl Ann Ingman, and Meghan Walker.
Promotional Graphics by Mary Stratton, photography by Sarah Woolf, and theme music by Jonah Cohen Sound. A huge thanks to the entire Her First $100K community for supporting the show. For more information about Financial Feminist, Her First $100K, our guests and episode show notes, visit financialfeministpodcast.com. If you’re confused about your personal finances and you’re wondering where to start, go to herfirst100k.com/quiz for a free personalized money plan.
Tori Dunlap
Tori Dunlap is an internationally-recognized money and career expert. After saving $100,000 at age 25, Tori quit her corporate job in marketing and founded Her First $100K to fight financial inequality by giving women actionable resources to better their money. She has helped over five million women negotiate salaries, pay off debt, build savings, and invest.
Tori’s work has been featured on Good Morning America, the New York Times, BBC, TIME, PEOPLE, CNN, New York Magazine, Forbes, CNBC, BuzzFeed, and more.
With a dedicated following of over 2.1 million on Instagram and 2.4 million on TikTok —and multiple instances of her story going viral—Tori’s unique take on financial advice has made her the go-to voice for ambitious millennial women. CNBC called Tori “the voice of financial confidence for women.”
An honors graduate of the University of Portland, Tori currently lives in Seattle, where she enjoys eating fried chicken, going to barre classes, and attempting to naturally work John Mulaney bits into conversation.
