Don’t ask ‘How much do you make?’ on a date—ask these 7 questions instead

Dating is full of tiny money moments: choosing a restaurant, talking about travel, splitting a check, and deciding whether a gift is “too much.” 

You don’t need to ask someone how much they make, what their net worth is, or how much student loan debt they carry to learn how they approach money and what kind of financial partner they might be.

Talking about money with a potential partner is never just about money. It’s about values, habits, and expectations around how someone thinks a “team” should work.

On your first few dates with someone, can you imagine actually asking, “How much do you make?” Or, “What’s your net worth?” I wouldn’t be surprised if they excused themselves to the restroom and didn’t come back. 

The irony is, those questions aren’t even the best way to get at what you’re trying to learn. Someone can earn a lot and still feel financially unstable. Someone can earn less but have excellent systems, habits, and boundaries.

The goal is to understand how they think about money and what their values are. 

Start with these questions that invite real answers, stories, preferences, and patterns — and reveal their financial mindset more organically.

1. “Where did you grow up and what was it like?” It’s a basic getting-to-know-you question, but you’ll learn a lot about the environment they were raised in, their family norms, and the lifestyle they consider “normal,” without forcing them into specifics.
2. “Tell me about your family. What were they like when you were a kid?” People will tell you what shaped them if you give them an opening. Pay attention to themes like stability, ambition, generosity, privacy, education, status, faith, and community. These are the things that drive financial decisions.
3. “What was your first job?” This is an easy way into someone’s relationship with work, motivation, and independence. Did they feel proud, pressured, supported, or alone? Did they work well with other people? Those early experiences tend to show up in adulthood, including how someone thinks about earning and financial stability. A first job often reveals what money represents to them: freedom, security, responsibility, or survival. It can also hint at their default habits, like whether they saved their first paychecks, spent them immediately, or used them to help their family.
4. “Are you more of a planner or a wing-it person?” This is a window into how someone handles uncertainty, and money is full of uncertainty. Two people can be completely different here and still work, but it helps to know what you might be signing up for early on — before life gets busy and important financial decisions have to be made.
5. “What’s something you’ll happily spend on and something you refuse to overpay for?” Most people have “yes” categories and “no” categories that reflect their values. You can learn how they perceive things like convenience, health, quality, experiences, style, generosity, and savings. It’s also a great way to talk about spending without getting into budgets.
6. “What’s your ideal vacation?” Vacation preferences are just as much about money expectations as they are about travel. A “camping in national parks” person and a “boutique hotel and tasting menu” person can find common ground, but it’s helpful to learn early what someone assumes about cost and how they handle it when planning trips with other people. Do they openly talk about a budget before booking, or hope it all just works out?
7. “When you get stressed, what do you like to do?” You’re not fishing for a perfect answer. You’re learning how someone copes with stress, because stress changes how people spend, save, and communicate about money. Some people plan. Some distract. Some shut down. Some spend. The key is whether they recognize their patterns, because self-awareness is what allows us to better manage our behaviors.

When money stops being theoretical and starts showing up in decisions that affect both of you — moving in, splitting regular expenses, building a shared life — it’s time to have more direct and specific conversations.

Money doesn’t have to be a third wheel on your early dates with someone new. Start with questions that reveal how they think and live, and save the hard numbers for when you’re building something together. That’s how you avoid surprises and set the relationship up to last.

Douglas A. Boneparth is the president and founder of Bone Fide Wealth, a wealth management firm based in New York City that focuses on millennials, young professionals and entrepreneurs. He is a member of CNBC’s Financial Advisor Council. Boneparth and his wife, Heather, are the co-authors of “Money Together: How to Find Fairness in Your Relationship and Become an Unstoppable Financial Team.” 

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