A question I occasionally get (though, not too often since I mainly work with people in the very early stages of meeting and new relationships) is this: “When should I ask the person I’m dating about their finances?”

This has been especially relevant lately in light of the movie "Materialists" out right now about a matchmaker is working with clients to find their dream partners, many of whom have very strict salary requirements (which is, honestly, hard to watch but not untrue for many). Meanwhile, the matchmaker in the film is also struggling with herself as far as whether someone’s financial prowess outshines true love (with a guy who is, in his own words, “broke”).

I’ll start by saying that I find that people are so keen on (obsessed with?) not “wasting time” that they often ask questions, about finances or otherwise, prematurely and completely out of context. Instead, you’ll learn a lot more about someone’s finances—both how much they may have and how they choose to spend their money—simply by spending time together. For example, does the second date include a fancy, expensive dinner, or is it a drink and a walk through the park? Do they fly first class and travel monthly or save for an annual trip to the beach with their children?

Observing how someone actually lives their life is a lot more telling than asking someone a question too soon -- a question that they may or may not answer honestly.

Here's my advice: I don’t recommend asking explicit questions about someone’s finances early on, especially in the first few dates. You may think you’re saving time, but in the process of essentially interviewing your date for a “right” answer, you may also be putting them on the defensive and making them think that the only value they have to you is the number of dollar signs in their bank account.

This is also true for premature questions about prior relationships (the first date is not the time to pry into the reasons someone got divorced … not your business), health issues, difficult family matters or custody situations. The first date is simply to see if you get along … and might want a second date. That’s it!

Also, try not to jump to conclusions about someone’s financial situation simply from their job type.

I, sadly, have a lot of people say, “I would never date a teacher. They don’t make enough.” I will retort, “1) We have no idea what their financial situation looks like, and 2) Do you not find it commendable that someone would dedicate their life to helping young minds?” Whether my prodding gets through to people or not is questionable, but gosh darn it, I try.

As you progress in your relationship, things will come up. The first might be a trip you’re planning to take together. This would be a good time to start gauging how someone handles money. You can ask, “Are you more comfortable at a hotel or an Airbnb?” or “If we went to one of the nicer restaurants on vacation, how would you feel?”

Ultimately, however, if you’re planning on merging anything, especially a home or considering getting married (or having children), it is important to discuss finances. No singular aspect covers everything, so make sure you discuss not only income but career goals, debt, savings and investments, and retirement planning (including when you each want to retire and potentially where).

Ultimately, the key to understanding someone’s financial situation in a relationship is balance and timing. Over time, as your relationship progresses, conversations about finances will naturally come up. When that happens, approach the discussion with care, understanding and a willingness to listen.

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