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Talking about money early in a relationship can feel daunting. Money is often rooted in fear and shame, which can make intimate conversations uncomfortable, especially when you’re still trying to keep things light and fun.
However, as a family law attorney for nearly a decade, during which time I have represented high-net-worth clients through cohabitation, marriage, kids and divorce, I can attest to the value of gauging your potential partner’s money values early on. I’ve seen how financial conflict can erode even the strongest relationships. Too often, couples never talk about money and they pay for it later.
I’m not saying you should ask your date about their 401(k) balance on the third date. But there are five essential questions you should ask by this point. That way you can spot any red flags before your heart is in too deep.
1. ‘If you won the lottery today, what would you do with the winnings?’
Asking hypotheticals, no matter how wild they might seem, can offer insight early on to your partner’s financial values. There are many possible answers to this question, starting with whether they would take the winnings in a lump sum or in installments.
They might want to spend it all, start saving, pay off student loans, support their family, quit working, start a business or travel the world. Their answer, whatever it may be, offers a window into their aspirations, obligations, and relationship with money.
2. ‘What was your first financial surprise and how did you handle it?’
How someone handles the unexpected tells you a lot about them. Are they prepared, reactive, hysterical, or do they live in denial? Do they lean on their parents or friends, accumulate high interest debt or tap into their emergency savings?
Their response to past experiences may reveal how they will adapt, grow, and plan for what’s next, no matter what is thrown at them. You want to figure out how they will navigate challenges with you in the future.
3. ‘How did your parents talk about money growing up?’
Our financial foundations are largely shaped by our upbringing. How your partner’s parents managed money and discussed it with them will carry into adulthood and how they handle it in your relationship.
For example, if their parents never discussed money, they might carry shame around the topic or feel uncomfortable discussing it with you. They might respond defensively to money questions without realizing it. They also might avoid open and honest money conversations with you altogether.
Or, if they never heard “no” or had unlimited access to a credit card, they may carry a sense of financial entitlement, which can create friction if it spills into your relationship without established boundaries early on.
This could look like your partner assuming your income is “our money” while their income is “their money.” They might spend shared money without considering the impact on you or your joint goals. They also might expect you to maintain a lifestyle beyond your means or comfort, or that they couldn’t otherwise afford, because they “deserve” it.
Understanding your partner’s financial upbringing gives you insight into their current habits and expectations, which creates a framework for how you can expect to handle money together.
4. ‘What was the first thing you splurged on when you started making money?’
How someone celebrates their financial successes can reveal their financial priorities.
Whether they use the funds to pay off student loans, buy a new car, splurge on a vacation or another luxury item, their answer can provide insight to whether they value security, status, freedom, or experiences.
It may also hint at how they may handle money as your relationship, and their income, grows.
5. ‘What is something you are saving for or working toward financially?’
This question reveals more than just your date’s savings goals. What someone is working toward can give you an insight to their values, planning habits and life priorities.
Depending on their answer, you may be able to assess if they are a long-term planner, driven by experiences, focused on security or just living in the moment.
For example, if they are putting money toward a down payment of a home, a new business, their retirement, or even for their future children’s education, you are looking at a long-term planner and someone who may be family-oriented.
If they are dreaming of a vacation or saving up to take a gap year to travel the world, they may prioritize experiences over possessions. If they are eyeing a luxury car or piece of jewelry, that may reveal they are status-driven. Or, if they have no goals at all, that tells you something, too.
As uncomfortable as it may feel, talking about money does not have to be unromantic. The strongest successful relationships thrive on open and honest communication. Addressing these topics early can lay the groundwork 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 diverse range of industries, including sports and entertainment, content creation, finance, tech, and innovation. Jackie is a Matrimonial & Family Law Partner at Blank Rome and is the author of the upcoming book “Love Him. Check Everything” (Simon & Schuster, 2028), advice for women on building financial intimacy with their partners and protecting themselves in relationships from first date to final settlement.
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