A Sneaky Way to Talk Money on a First Date Without Making Things Awkward

When Krista and Danny met, Krista was living in Baltimore and working as a teacher’s aide. She didn’t make much money. She used food stamps to supplement her income, and she had not paid a penny toward her $40,000 in private and federal student loan debt in years.

Danny was working as a financial aid adviser. So it’s not surprising that their conversation eventually landed on her mountain of debt.

By the end of the date, Danny had already helped Krista work up the courage to call one of her lenders and make a payment over the phone.

“I just felt isolated, but then, having met Danny, I just didn’t feel that way anymore,” Krista told host Anna Sale in a recent episode of the podcast “Death, Sex & Money.” “It stopped becoming my identity, and it started just becoming something that… can be controlled but doesn’t control me, and that was a huge revelation.”

Yes, this was their first date. No, this is not weird. In fact, Sale called it “the most beautiful, sweet thing,” and I agree.

We’ve been trained to believe that if we want conversations to remain civil, we are supposed to steer clear of conversations about money.

And when it comes to first dates, we seem to double down on that rule.

But if you believe that, I can tell you right now that you probably don’t want to go on a date with me because that’s where I’m taking the conversation. (While we’re at it, we’ll probably discuss religion and politics, too.)

Backtracking on that crush you thought you had on me? It’s cool. Don’t ask me to dinner. But at least hear me out before you decide to disagree with me. I’ve got proof.

You and Your Boo May Not Be on the Same Page About Money

The Cashlorette, a blog run by Bankrate analyst Sarah Berger, conducted a survey about our views on money and dating last month.

On some things, men and women were pretty close. For example, men think a first date should cost $89.94 on average. Women thought it should cost a few dollars less at $83.97.

The survey showed that 85% of men thought it was their responsibility to foot the bill for the first date. That’s a good thing because only 8% of women said they expected to pay the full bill on a first date. (In our defense, 37% of women said they expected to split the check.)

Unfortunately, other disagreements over money can cause problems.

According to the survey, 51% of people who are married or have a live-in partner said they have gotten into a fight about money at some point in their relationship.

Of those who fought about money, 59% said the fighting started because one person in the relationship thought the other was either spending too much or was entirely too cheap.

Another 16% percent of couples who said they fought over money said it started because someone lied about their spending habits, while 14% said they got into arguments over how to divide up bills.

While it’s impossible to know everything about your new boo and their relationship with money in a single conversation on a single date, a few key questions might help you avoid partnering up for life with a cheapskate if you’re a big spender.

Don’t Ask ‘Are You Rich?’

I’m… blunt. When I’m not careful, as soon as thoughts enter my head, they come tumbling out of my mouth.

That happened a few days ago with a guy I met at a bar while out with a few friends. He went on and on about how he moved to Florida because he got a huge raise at his new job and how he made so much more money now than he did before.

He brought it up, so I asked the question everyone was thinking: “Are you rich?”

This wasn’t a date. This wasn’t someone I was trying to build a relationship with. But this was someone I just met. I shouldn’t have to say this, but if you’ve never talked about finances on the first date and you want to start, this is not the way to do it.

Instead, just work it into the conversation casually, and ask questions that allow you to make a few inferences about your date’s financial stability.

For example, ask your date if he likes to travel. If he does, look for specifics.

If he rattles off an endless list of countries and cities he has visited, you know that he likes to spend money on experiences, but that might not be enough to gauge his spending habits.

Follow up with questions and find out if these were work-related trips or just for fun. Ask where he stayed. Is he staying in hostels and spending $20 a night on backpacking trips? Or is he the type to drop $300 a night on the swanky hotels for 10-day excursions?

Just like that, a simple conversation about traveling can teach you about how your potential partner spends. And you can compare this information with your own spending habits to gauge whether you’d be among the 51% of couples who fight about money.

And that’s just one way to approach it. Is your date a music lover? Ask about concerts or music festivals. Did your date say he’s foodie? Find out if he likes to cook or if he just moved to your city but has somehow tried every restaurant in town.

As you go on more dates and get more comfortable, you can ask more direct questions to make sure you’re right about the first date inferences. Not only is it informative, it’s painless.

Desiree Stennett (@desi_stennett) is a staff writer at The Penny Hoarder. She’s also single, so it’s possible that she’s wrong about this. Anyway, she’ll see you on Tinder. Happy swiping.