My Date Paid For Dinner — & This Is How I Feel About It

Illustrated by Richard Chance.
The end of a date is, hopefully, full of feelings. But one of these feelings is more awkward than the others: Raise your hand if you've fumbled, engaged in the tried-and-true wallet reach, or said "oh no you shouldn't have" when a date insists on paying the whole check.
The world of heterosexual dating can feel like the last frontier in overcoming old-fashioned gender roles and stereotypes. It goes without saying that you can be a hardcore feminist and appreciate when a guy holds open the door or picks up the bill on a date. Conversely, it shouldn't be emasculating to a guy when a woman offers to pay. But is it okay to feel a tinge of disappointment if you go splitsies?
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Let's face it: the check on a date can be really awkward to navigate. There is a slew of factors to consider: If you know your date makes three times your salary, is it incumbent upon them to pick up the check? Or should you just split the difference the whole night no matter who makes what? And to what extent does ego play into the whole thing?
Ahead, four recent Money Diarists dive into how they felt when their dates picked up the check.
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1 of 4

"When L. paid on our first date, I was in the bathroom."

This 23-year-old aerospace engineer in Englewood, CO, toggles between a few prospects (she met L. on Coffee Meets Bagel, and B. on Bumble) over the course of her Money Diary.

How did you experiences with L. and B. compare in terms of payment?

"On our first date, L. bought the drinks, and on our second date, I bought the drinks. For our third, he came over to my place to watch a movie and brought a six-pack of beer. But when I went on a date with B., he bought a drink and closed his tab prior to me arriving, so I ended up paying my own tab."

What happened when the check came on your first date with L.?

"When L. paid on our first date, I was in the bathroom, and when I returned, he stated that he got this one but I could get the bill next time. I found this interesting because we hadn't officially decided to go on a second date, so I'm not sure if he actually wanted me to buy next time or if he was just trying to segue into us going on a second date."

What is your philosophy when it comes to paying on first dates?

"Usually on first dates, I don't offer to pay, but I am very willing to if asked. If we go to multiple places or have multiple rounds of drinks, I usually offer to buy the second time, because I can afford to. Equality!"
2 of 4

"I’ve noticed younger men are keener to split the check on first dates."

This 35-year-old project manager from San Francisco, CA, went on two dates with a guy she met on Hinge in one week (and then hopped into her Money Diary comments with an update: the second date was their last). She admits going back and forth on how she feels about dating apps, bemoaning how much of her time they tend to take up.

What happened when the check came on your first date?

"He reached for his wallet immediately. To me, that’s usually a signal that he intends (and wants) to pay. Although I did half-reach for my wallet as well, he motioned that he had it, and that was that. He asked me out and chose the restaurant, so, despite it being our very first date, I was expecting him to pay."

What about your second date?

"He bought us movie tickets online prior and paid for our drinks at the bar while waiting for a table to open up at the restaurant. I was already planning to pay for our food at that point, and he let me. He didn't reach for his wallet."

What's your philosophy when it comes to paying on first dates?

"If a man asks me out and recommends a bar or restaurant, I assume it’s within his budget and he’s planning on paying. The way I feel is, if money is a concern, choose a date that you can afford. This goes for both sexes. A coffee date or a free art exhibit works. I typically think the adage “whoever asks, pays” works most of the time. Although, I’ve asked men out for a first date and they’ve insisted on paying – even when I offer. In this case, I graciously accept.

"I’ve noticed younger men are keener to split the check on first dates, and they handle this by flat out mentioning it when the check comes. I don’t love this, to be honest. I find men closer to my age (35 or older) typically insist on paying for the first date. Maybe they are more financially stable? Old-fashioned? If we are having a great time and the man makes it clear he wants to pay, all the better. I'll offer to pay on our next date. Everyone likes to be treated. If a date isn’t going so well and I know I won’t see the person again, I'll offer to split the check right away. I've learned to always carry cash!"
3 of 4

"They want to appear as successful, able providers – and you paying their share is a blow."

We met this 26-year-old sales director in Brooklyn, NY, on her fourth date, where she was verbally harassed by a girl in the bar bathroom (and got the bouncer involved), before heading back to her date's place for some wine and rooftop skyline-gazing.

What happened when the check came?

"After our first three dates, I knew he didn't expect me to pay, so I let him pick up the check without any discussion. My date had a successful professional background and was also over ten years older than me. I feel like in those situations (where the man is clearly more established financially), they go on the date expecting to pay for everything. I would never assume that someone earning more money should be responsible for paying the tab, but it also does feel silly arguing over a bar tab with someone who makes over twice my salary. He also paid for my Uber to go home."

What is your philosophy when it comes to paying on first dates?

"I always offer to split the bill. This guy was the type who takes the bill directly from the waiter (before it even hits the table). In those situations, I'll offer to pay next time. After two or three dates, if I see a pattern (like if they swoop for the check), then I'll assume they enjoy treating me. I think when men take responsibility to pay for everything, it's partially driven by ego. They want to appear as successful, able providers – and you paying their share is a blow."
4 of 4

"If it's a not-so-great date and I just want to get out of there, I'll offer to split the bill."

This 24-year-old copywriter in Massachusetts went on two dates with a guy she recently started seeing. She says she foots the bill for their outings one-third of the time, because he makes three times her salary.

What happened on your dates when the check came?

"He paid for everything on our first few dates, and now that we've been regularly going out for the last few months, we take turns more often. We've had brief discussions about our finances, and he makes a significantly larger salary than me and has less debt, so he usually pays for pricier outings."

What is your philosophy when it comes to paying on first dates?

"On first dates, I usually let my date pay for me. If we go to dinner and he pays, and then go for a drink or dessert somewhere, I would pay. In my experience, the guy usually insists on paying. I think a lot of it depends on the chemistry of a date, and several guys have told me that if the girl is insistent on paying or splitting the bill, it makes them feel like she doesn't want to go out with them again or take things further. If it's a not-so-great date and I just want to get out of there, I'll offer to split the bill. I think the more I have dated, the more I have preferred to keep early dates as low-key as possible – like going to a dive bar instead of an expensive meal. It's easier, logistically and economically, to take turns buying rounds of drinks."

This interview has been edited and condensed for clarity. Have a story you'd like to share? Email us here.
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