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

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.

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

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

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

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.

“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.”

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