How One Man Spent Over $700 On 14 Dates In 30 Days

Illustration by Abbie Winters.

The lead-up to any special occasion can arouse a number of conflicting feelings: Excitement of the possibilities, whether it's a big date or friend's wedding; or anxiety about the behind-the-scenes prep work — namely, keeping your calendar in check and your bank account in the black.

One of the things we've learned at Refinery29, through Money Diaries and Not A Trophy Wife, is that observing how other people negotiate their finances can inspire us to consider, and even change, our own habits — or simply reassure us that we're already doing our best. Now, in our new series, Keep The Receipts, we're tracking how people make their way through a month of life events, big and small.

First up, a 26-year-old straight man in New York City explains how he dates — and what he spends — after years of being in a relationship. He started dating in mid-February, and met seven women through apps — specifically, Bumble and Coffee Meets Bagel. In 30 days of dating, he spent $771 at wine bars and movie theaters, on dinners both big and small, and brunch (of course). Read on to see if all that dating was worth it.

Total: $771 for 14 dates over 30 days

Week One

Date #1: Wine bar — $91
Date #2: Bar — $40
Date #3: Dinner & drinks — $70
Date #4: Dinner ingredients (cooked at home; date paid for half & cooked) — $40

Week Two

Date #5: Movie & drinks — $50
Date #6: Dinner (split the bill) — $40
Date #7: Movie — $36
Date #8: Dinner & drinks at Freek's Mill — $130

Week Three

Date #9: Dinner (followed by a break-up) — $60
Date #10: Benefit event — $0 (plus one for date's work event)
Date #11: Dinner (Cooked at her place) — $0

Week Four:

Date #12: Drinks — $19
Date #13: Brunch — $75
Date #14: Dinner — $14

You spent as little as $40 on some of these dinners. But on one second date at Freek's Mill — a more upscale restaurant — you had a $130 dinner bill? That's a big range.

"If it's a $40 dinner, that probably means someone insisted on paying half. At Freek's Mill, I think we ordered about five food items, and I was the only one who got a drink because my date wasn't feeling great."

Were you actively choosing places that were cheaper, or did you pick restaurants that you wanted to go to anyway?

"Where we went usually depended on what my dates were in the mood for or where they live. A lot of places I wanted to try were a little expensive for a second or third date."

Did you have any strategies for dating over the course of the month, or did you come up with one by the end?

"I started avoiding dinner on the first date, which was a mistake I made earlier. Aside from that, I didn't really have a strategy. Second date was usually dinner or drinks again, but more often than not, dinner. I’m cost-conscious — but not exceptionally so."

Why did you stop having dinner on the first date?

"I had a pretty memorable bad first date over dinner. It was clear early on that we weren't going to work out, but with dinner, you’re locked in — in terms of time. Trying to make the conversation drag on as long as possible so that we could order and get through it was like pulling teeth. We went to Calexico, so it wasn’t actually super expensive. It was probably $50 or $60, and I covered the entire bill."

So, you prefer to go out for drinks on the first date?

"Yes, but depending on how well that date goes — drinks can add up. I usually ordered just one or two drinks. I’m not looking to get hammered on a first date. If you are, it’s probably an indication that it’s probably not a great first date."

How do you navigate the bill question — who pays for dinner, etc.? Do you expect the wallet reach?

"It depends on how well the date is going. I don't make any judgments based on whether the girl tries to pay or doesn't. My default is to move to pay for the whole thing, and also to resist them trying to. Every now and then, I'll go out with someone who is insistent, but it's pretty rare. They'd have to insist four or five times. I can be pretty stubborn.

"If she did pay, I would be pretty insistent on Venmo-ing her back. I grabbed a drink with the girl I'm seeing now, and I got the check first. I had opened a tab on my credit card at the bar, but when she got there, she ordered a drink, swapped out my credit card for hers, and sneakily paid the bill. In that case, we'd been on enough dates that I was less insistent than I would have been on a second or third date."

Why are you less insistent over time?

"It's just a sense that that is what you do. Also, generally speaking, the girls I've been on dates with become more insistent that we share expenses over time.

"If it was a long-term thing, I would not be okay with a girl who didn't offer. I think there is a shared responsibility that enters a relationship. I haven't given a ton of thought into the point at which I would start to get a little bit annoyed, because I think it's pretty atypical. But there is definitely a point in my mind when become reasonable — if not expected — to start sharing things."

If we count just how much was spent on you (by cutting your month-long dating tab in half), you've spent about $385 on food and drinks for yourself during this period. Does that number feel like a lot?

"It felt like a lot to me — at least for a month-long period. I wasn't going out to dinner a ton when my ex and I were together, so the cost certainly felt larger. It's not just what I spent on my dates; it's the added cost of spending more than I ordinarily would on myself. It would have been even more if I hadn't started pruning the crowd, so to speak. Part of that is informed by the fact that I traveled three out of four weekends the month before, so I was feeling especially poor. But it was more than I expected."

How much do you normally spend on meals by yourself?

"If I weren’t dating, and I was eating out by myself — like a nice dinner — I would probably spend somewhere in the ballpark of $60 to $70. I would either go somewhere nicer intentionally, or I would order more food, or a more expensive item on the menu. But I wouldn’t be doing it all that frequently."

So, do you order differently on a date than you do when you go out to eat by yourself?

"I will sometimes modify what I order. I don't generally watch what my date is doing. I may not get an appetizer, or I'll move toward something a little cheaper — at least until later on in the dating process. I'm trying to be cost-conscious and gauge whether or not I am spending more than the average guy does on dating. I've been in long-term relationships for the last seven or eight years, so I don’t have the best barometer.

"I wouldn't necessarily be going out otherwise, and if I did, I would definitely be spending a lot more money. When my ex and I were together [in a long-term long-distance relationship], we would go out and do something nice — but that was because we only saw each other once or twice a month. It was easier to justify a nice night out every now and then, but if you're going on dates two to four times a week, that adds up."

You had a $60 dinner that ended up with a breakup during the meal. What was that about?

"It sort of felt appropriate? I mean, breaking up was going to happen regardless. It was around dinnertime, and we were going to eat anyway. I'm still operating very much on the guy-should-pay-for-things mentality I was raised with. So, even if I had the intention of breaking up, it still felt appropriate to pay for dinner."

Why didn’t you just meet for coffee?

"I probably would have preferred that, but she asked me what was going on that night. I didn't want to start that conversation over text, so we sort of wound up with dinner instead."

Does this experiment change the way you see dating?

"I didn't have any preconceived notions of my dating habits. I hadn't actively dated since high school, so it certainly informed me of my baseline dating habits."

How do you feel about your decisions?

"From a cost perspective, it doesn't feel that crazy. From a time and energy perspective, it was definitely tiring. Even before I decided to focus on just one girl, I was getting a point where I wanted to slow down a bit."

Interested in sharing your own month of receipts? Tell us at moneystories@refinery29.com.

Related Video