Talking about money once you start dating can be daunting. Money is often rooted in fear and shame, which can make intimate conversations uncomfortable, especially if you’re trying to keep things light and fun.
However, as a family law attorney for nearly a decade representing high-net-worth clients in cohabitations, marriages, children, and divorces, I can attest to the value of assessing a potential partner’s financial worth early on. I’ve seen how financial conflicts can undermine even the strongest relationships. Often, couples don’t talk about money at all and pay for it later.
I’m not saying you should ask your date about their 401(k) balance on the third date. However, there are five important questions to ask by this point. That way, you can spot the red flags before you get too deep.
1. “If you won the lottery today, what would you use your winnings for?”
No matter how far-fetched they may seem, developing hypotheses can give you early insight into your partner’s financial value. There are many possible answers to this question, starting with whether you want to receive your winnings in a lump sum or in installments.
They may want to go all in, start saving, pay off student loans, raise a family, quit their job, start a business, or travel the world. Their answers, whatever they are, provide a window into their aspirations, obligations, and relationship with money.
2. “What was your first financial surprise and how did you deal with it?”
You can tell a lot about someone by how they handle unexpected situations. Are they ready, reactive, hysterical, or living in denial? Are they relying on parents or friends, accumulating high-interest debt, or tapping into emergency savings?
Their reactions to past experiences may reveal how they adapt, grow, and plan what happens next, no matter what is thrown at them. You want to know how they will overcome challenges with you in the future.
3. “How did your parents talk about money when you were a child?”
Our economic base is primarily formed by our education. How your partner’s parents managed money and discussed it with them will influence you even into adulthood, and how they handle it in your relationship.
For example, if your parents have never talked about money, they may feel embarrassed about the topic or uncomfortable discussing it with you. They may react defensively to questions about money without realizing it. They may also avoid having open and honest financial conversations with you altogether.
Alternatively, if the other person has never heard the word “no” or never had unlimited access to a credit card, they may harbor a sense of financial entitlement, and if that spills over into your relationship without establishing boundaries early on, it can cause friction.
This may look like your partner is assuming that your income is “their money” while yours is “their money.” They may spend shared money without considering the impact on you or your joint goals. They may also expect you to maintain a lifestyle that is beyond your means or comfort, or that you cannot otherwise afford. Because it’s natural for them to do so.
Understanding your partner’s financial background provides insight into their current habits and expectations, which creates a framework for how you can expect to handle money together.
4. “When you started making money, what was the first thing you splurged on?”
How a person celebrates financial success can reveal a person’s financial priorities.
Whether they’re using the money to pay off student loans, buy a new car, or splurge on vacations or other luxuries, their answers can tell you whether they value security, status, freedom, and experience.
It may also give you tips on how they handle money as your relationship and income increases.
5. “What are you doing to save money or work on your finances?”
This question reveals that it’s not just your date’s savings goals. Knowing what someone is working toward can tell you about their values, planning habits, and life priorities.
Depending on their answers, you may be able to assess whether they are making long-term plans based on their experience, focusing on security, or just living in the moment.
For example, if you’re putting money toward a down payment on a home, a new business, retirement, or even your future children’s education, you’re looking for someone who is a long-term planner and someone who values family.
If you’re dreaming of a vacation or taking a gap year to save up to travel the world, you’re likely prioritizing experiences over possessions. If they are interested in luxury cars or jewelry, it may reveal that they are status-driven. Or if you don’t have any goals at all, that also says something.
Although it may feel uncomfortable, talking about money doesn’t have to be unromantic. The strongest and most successful relationships thrive through open and honest communication. Addressing these topics early can lay the foundation for a strong partnership built on shared values, aligned goals, and genuine connection.
Jackie Combs is an experienced negotiator known for handling celebrity and high-profile cases. She represents high-net-worth clients across a variety of industries, including sports and entertainment, content creation, finance, technology, and innovation. Jackie is a Marriage and Family Law Partner at Blank Rome and the author of the forthcoming book “Love Him. Check Everything” (Simon & Schuster, 2028). This book is advice for women on building financial intimacy with their partners and protecting themselves in relationships from the first date to the final settlement.
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