5 Money Icebreakers for Better Money Conversations

September 28, 2022

Now Trending:
I'm Tori!

After successfully saving $100,000 at age 25, I quit my corporate job in marketing to fight for your financial rights. I’ve helped over three million badass women make more, spend less, and feel financially confident.


The following article may contain affiliate links or sponsored content. This doesn’t cost you anything, and shopping or using our affiliate partners is a way to support our mission. I will never work with a brand or showcase a product that I don’t personally use or believe in.

Most people today would rather talk about sex than money.

At least that’s what journalist Gaby Dunn found as she surveyed strangers for a 2016 article, and she isn’t alone in her findings.

A recent survey found that one in ten people would rather talk about the details of the horizontal shimmy with their parents than ask them for financial help.

Needless to say, the reality today is that most people would rather talk about just about anything other than money.

Why? Well, money is really personal, and disclosing financial information to a friend, family member, partner, or even financial professional can feel intimidating, scary, or even shameful – especially if your money situation isn’t exactly where you want it to be just yet.

But here’s the thing: talking about money is really important. Having transparent financial conversations can help close the gender wage gap, improve financial literacy in your community, encourage women to advocate for themselves in the workplace, enable people to leave financially abusive relationships, allow you to find essential financial information, and so much more.

Now we know that talking about money is a lot easier said than done – after all, we have built a multi-million dollar business answering the financial questions others shy away from. But we don’t want the discomfort of talking about money to hold anyone back from improving their relationship with money, getting out of a bad financial situation, or living a life of financial freedom.

So today we are going to help you have better and easier money conversations with your friends, coworkers, loved ones, partners, and neighbors by sharing five of our favorite money icebreakers.

Two women drinking coffee and sitting at an outdoor table while smiling.

What the heck is a money icebreaker?

We are so glad you asked!

While we eventually want you to feel comfortable discussing the ins and outs of your finances with the appropriate people in your life, we understand that jumping into those conversations with both feet can be really overwhelming for a lot of people. That is why we came up with the idea for money icebreakers for better money conversations.

Money icebreakers are questions that are created to spark money conversations that feel fun and judgment free and can “break the ice” to having more serious, vulnerable financial conversations. 

While we are sharing five of our favorites today, we recently released a collection of 30 money icebreakers that you can use with a romantic partner, friends, family members, coworkers, or anyone who would benefit from a transparent financial conversation. The best part? They’re totally free!

Now, let’s get into our five favorite money icebreakers and why they are our favorites (and will quickly become yours too).

  1. Do you believe “money can’t buy happiness?” Why or why not?

HFK Founder, Tori Dunlap, shared some thoughts on whether or not money can buy happiness on Season 2 Episode 1 of the Financial Feminist podcast.

Just about everyone has heard this phrase at some time or another, so most people have an opinion on it already, making this an easy and familiar icebreaker to start paving the way for deeper financial conversations.

Some follow-up questions could be:

“Are there things that cause happiness that money can buy?”

“Do you feel like your happiness is ever affected by money?”

“Do you think our happiness should be affected by money?”

We explored the relationship between money and happiness in a recent Financial Feminist podcast episode. Listen to the full episode exploring three patriarchal money  myths that keep women from building wealth here!

2. Would you rather have a low-paying job that you love or a high-paying job that you hate? Why?

This is our take on the classic “would you rather” question.

We love this icebreaker because the conversations that arise from this question often reveal what our individual priorities are. From financial security to a fulfilling career to a work/life balance, this icebreaker really helps to explore what our greatest motivators are, thus providing more context and empathy for future money conversations.

Some follow-up questions could be:

“Where does your current job fall in relation to this question?”

“What role does your career serve in your life?”

“Do you get a lot of personal fulfillment from your job?”

“How important is it for you to love your job?”

“What do you look for when applying for a job?”

“What does your dream job look like?”

Pssssst…did you know that you can have a job that you love and that pays well? You might just need to do some negotiating to get it. Learn how to negotiate your way to your dream job and dream pay rate in our bestselling Navigating the Negotiation course.

Three female coworkers sitting at a table and happily reviewing work documents.

3. What role does money play in your life?

This is one of our favorite icebreakers because, at first, it seems like such a simple question. But the longer you sit with it, the more you can start to unpack the various roles that money plays in your life.

From allowing you to pay your bills to providing a sense of financial security to being a source of stress while also a source of peace, money often plays multiple and complex roles in people’s lives – roles that may not even be realized until this question is explored.

Some follow-up questions could be:

“What role do you want money to play in your life?”

“What roles do you think money should play in your life?”

“What role do you think money plays in my life?”

“How has the role money plays in your life changed as you have grown up?”

4. How does thinking about money make you feel?

On the vulnerability scale of “what would you buy if you won the lottery?” to “how much debt do you currently have?”, we would consider this icebreaker to fall right in the middle: it doesn’t require explicit financial information, but it definitely requires a bit of thought and vulnerability, and that’s why we love it.

The reality is that most people have a lot of feelings about money, and those feelings can differ from day to day, and even hour to hour. When asking this icebreaker, make sure to allow each person plenty of time to really sit with and share the various ways that thinking about money makes them feel. 

Some follow-up questions could be:

“How would you like to feel when you think about money?”

“How often do you find yourself thinking about money?”

“When do you feel best about money? Worst?”

Wish that you felt differently about money? Financial Feminist is the comprehensive manual you need to completely transform the way you think, feel, and use money. Written by HFK founder, Tori Dunlap, this book will give you the information, resources, and encouragement you need to own your financial sh*t in today’s modern world. Order your copy today!

5. Is there any part of your relationship with money that you would like to change?

This is a little bit of a trick question because – let’s be honest – most people would like to change some part of their relationship with money.

We like this icebreaker because it fosters a lot of reflective thought, builds vulnerability and trust, and also gives you some insight into what financial resources or support your friend, partner, family member, etc. may need. 

Some follow-up questions could be:

“Why do you want to change that part of your relationship with money?”

“How do you think you could change that part of your relationship with money?”

“I have a resource that could help you reach that financial goal. Would you like me to share it with you?”

“How can I support you as you work toward changing that part of your relationship with money?”

“Would you like to be accountability partners as we both work on improving our relationship with  money?”

We hope that these money icebreakers will help you start having more and more beneficial money conversations with the people in your life. 
Want even more money icebreakers? Don’t forget to download our FREE set of 30 Money Icebreakers here!

Take our FREE quiz for a personalized, step-by-step money plan 🤑



HFK Weekly

Subscribe to

Free money tips directly to your inbox