Success Story: Why Is It So Awkward to Talk About Money When You’re Dating in Your 20s?

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For a long time, talking about money in a relationship was considered awkward, intrusive, and sometimes downright rude. Yet financial transparency is one ingredient to a successful, happy relationship built on mutual trust and understanding. 

How to talk about money when you’re dating

Talking about money when you’re dating is actually a big, important step, especially now that most relationships involve two careers. This may be why millennials talk about money in relationships more than any other generation. 

After all, how could you agree to share bills with someone if you don’t know whether they prioritize making rent payments or running up bar tabs? Or accept a proposal without first knowing whether your future spouse had outstanding debts that could become your own? 

If you are wondering how to get rid of the awkwardness and dive straight into the money talk with your partner, you’ve come to the right place. I’ll walk you through how to host a money talk date night to learn more about your partner’s relationship to money. 

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Actionable Steps


Decide where to host your date night

The best place to host your money talk date night is at home, where you both feel comfortable and you don’t have to worry about who is footing the bill. If you do decide to venture out, choose somewhere quiet where you can hear each other talk and where you won’t face interruptions. 
If you are in a long-distance relationship, you can host your date night over a video conference call.


Play Money Talk games

Don’t start your money talk date night by demanding to see bank accounts or pay stubs. Instead, ease into the conversation with finance editions of icebreaker games. 
These money talk games let you learn about your partner’s relationship with money without being overly intrusive. 
You can delve into your partner’s past finance faux pas with a fun game of Never Have I Ever. Would You Rather is a great way to learn about your partner’s long term financial priorities and values, with questions such as “Would you rather have a shorter commute or a larger income?” 
You’ll find tons of free money talk games here. 


Express gratitude for your differences

Once you start having the money talk, it’s normal to come across some disagreements in opinion and priorities. No two people have the exact same views on money and you don’t have to agree on everything in order to have a happy, healthy relationship. 
Rather than tearing each other down or arguing about your differences, practice gratitude during your money talk. If your partner tells you they value spending money on vacations with friends, respond by saying “I think it’s great how you value relationships with both your time and money.” 


Set goals and boundaries

While you talk about money when you’re dating, set other goals and boundaries with each other. Talk about who pays for what, and how often. After all, it isn’t very fair for one person to pick up the tab every time you go out to eat unless you’ve agreed upon this ahead of time. 
Setting financial goals together can help you both envision your relationship long-term. Start by setting a goal towards a fun activity or trip you can do together. This will give you both something to look forward to as well as establish a unified goal. 
Having a talk about money when you’re dating doesn’t have to be awkward. In fact, it should be a fun and healthy conversation that helps set you and your partner up for long term success. While not every relationship you have in your 20’s is going to end in happily-ever-after, establishing healthy dating habits early on will set you on a path to success. 

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About the Author

Karlyn McKell

Karlyn McKell


Karlyn is a writer who specializes in the lifestyle and finance spaces. She believes the best ingredients for relationship success are passion, purpose, and open communication.

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