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On a first date? Watch out for these financial red flags

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A woman looks in her wallet for credit cards. (Joe Raedle/Getty Images)
A woman looks in her wallet for credit cards. (Joe Raedle/Getty Images)

Editor's note: This segment was rebroadcasted on April 29, 2024. Find that audio here

A date who requests $1.50 for a single eggroll after paying for dinner. Someone whose mother sends them money to take people out on dates. A potential partner who admits to overspending regularly on credit cards.

These could all be considered financial red flags that surface on dates. Behavioral red flags — like a date ordering for you, not asking any personal questions, or treating service workers poorly — are hot topics in conversations around dating. But The Washington Post’s personal finance columnist Michelle Singletary thinks financial compatibility is just as important when seeking a partner.

Singletary isn’t saying that you should open every first date by asking the other person about their income or what’s in their bank account. But there are other clues to look for to see if you and the other person have the same outlook on spending and finances. In her 32-year marriage, conversations about money with her husband started early on.

“At the beginning, he said, ‘Listen. I don't have a lot of money for our dates. So if it's okay with you, I might pay for some, you might pay for some, or we split it,’” Singletary says. “It turns out he was as frugal as I was.”

Singletary says it’s important for people to recognize their own values to know what they’re looking for in a serious relationship.

She says that before she met her husband, she went on a first date with someone who talked about buying their dream car, regardless of the cost, and going into debt over it. As someone who prioritized staying out of debt, Singletary didn’t plan a second date.

And she says that overspending is a red flag that daters should watch out for.

“They're living above their means. For me, that would be a huge red flag. Now, when you're dating, some of that can be kind of cute: ‘Oh, he takes me out. We fly first class,’” Singletary says. “All that seems really cute until you marry and you realize that there was all your money going to this reckless stuff that was fun when you were dating, but not when you're in a relationship and you're trying to build towards the future.”

Talking about money can be hard, but Singletary stresses the importance of doing it early on when seeing a new person. And if they aren’t comfortable having those conversations? Run. Financial attitudes and values shouldn’t be revealed after a relationship has become serious, she says.

“Dating should be the time that you kick people to the curb, and quickly,” Singletary says. “If you don't recognize the red flags, if you don't act on those red flags, you'll get all emotionally tied to this person.”

Some advice that worked for her? In her 20s, she asked her now-husband where he sees himself at retirement age. He answered by saying he pictures himself sitting on a porch watching his grandchildren play in the yard.

“I thought, ‘That's my man.’ And all of that meant that he shared my values,” Singletary says.

“You get to decide what your values are, and then you get to decide who you want to be partnered with in that respect. But the values have to be aligned.”


Kalyani Saxena produced and edited this interview for broadcast with Peter O'Dowd. Grace Griffin adapted it for the web.

This article was originally published on November 15, 2023.

This segment aired on November 15, 2023.

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