Keep The Receipts: How One Guy Spent Over $1,200 On 23 Dates In 30 Days

In our series Keep The Receipts, we track the extravagant costs of everyday living, as well as the less-common expenses tied to other life moments.

We first spoke with a man who spent more than $700 on 14 dates over 30 days. Next, we talked to a woman who spent roughly one-third of that on dating in the same timeframe. We also spoke to a woman who moved across the country, from New York to Los Angeles.

Today, we talk to a non-monogamous medical resident in his early 30s who went on nearly 25 dates across 30 days. He discussed his thoughts on dating in New York City, and how gender, money, and romance intersect.

The following interview has been condensed for clarity and length.

Scheduling is definitely an issue.

I have no idea how you managed to go on so many dates! Can you talk about how you managed them and why you made this a priority?

"Scheduling is definitely an issue. When you’re working 60-80 hours (or more) a week, it can be difficult. Honestly, when people aren’t good at scheduling things or are very 'play it by ear,' I don’t meet them. It's not that I’m excluding them intentionally; we just can’t find a time. It’s a combination of my work schedule and things I already have planned in my limited free time.

"In terms of making it a priority, it’s hard to know what’s normal. I didn’t know I was going on so many dates. A lot of my friends are in serious relationships, so they’re spending almost every day with their significant other. If you compare it to that, I’m actually spending less time with other people. But I’m extroverted; I get energy from meeting other people and there are a lot of very interesting, amazing people in New York City to meet."

Do you tend to date people in your field because they understand your schedule, or are you open to dating anyone?

"I don’t tend to date people in my field. Specifically, I would not date anyone in my own department because I think that’s a setup for disaster. I have dated residents in the past and there are advantages, but there are also perks to dating people outside of your field. It’s kind of nice to date people not in the medical field because they think what I do is super cool; there are all these peripheral ego boosts.

"If I was dating someone in the medical field, they’d be like, Yeah, yeah. Eighty-hour work week? Whatever. I don’t avoid people in my field, but given that most people are not [medical] residents, and I mostly date people I find on apps, I’m connecting with people who are just not in medicine."

I was a student making no money and still paying for everything; that made no sense to me.

What is your general approach to dating when it comes to finances — and how far along are you in your program?

"Not to the point where I make any money. My salary is between $70,000 to $80,000 but I have well over $250,000 of debt, so it can be hard. I’m of two opinions, the first being that in an ideal world where we are all equal, where women are getting a dollar to the dollar and have equal opportunities to get jobs and rise through those jobs, and in which they’re not penalized for child rearing, things should be split 50-50 on dates; that would be wonderful.

"When I ask my gay friends what they do for paying — because I think that’s an interesting population to look at for dating habits, as there aren't as culturally-engrained practices — one of the guys said, 'Well, it’s simple. If someone clearly makes more money, they pay; if you’re about the same in terms of socioeconomic status, you split the bill.' I told him, 'You don’t understand man; that makes way too much sense! Straight people are never going to go for that.' I would love things to be equal, especially for the first date because you statistically go on more first dates than anything else.

"But my other opinion is that’s obviously not the culture I live in. If I want to meet people, I’m going to have to obey the rules of the culture to an extent so, by and large I pay for first dates. I always appreciate a nod toward them reaching for their wallet or saying, 'Oh, are you sure?' Just making an acknowledgement. I have no expectation, but I certainly remember [an experience] when I was a medical student, and much poorer than I am relative to now, I went on a third date with a girl who was middle management at a very large company, and who I knew was making six-figures at that point. I was a student making no money and still paying for everything on the third date; that just made no sense to me.

"What I’ve tried to explain to my female friends is that not every quality guy out there — and in fact, most quality guys out there — aren’t making a ton of money. [For] women as a collective whole, it is in your best interest to split bills because [men] are then going to be able to go on more dates, and you’re going to have a higher likelihood of meeting them."

How do they receive that advice?

"Oh, they blow me off! These are my friends, but yeah, they blow me off. It's just ironic. Understanding the norms and practices that are expected of me, if I’m on a date with somebody I think is cool, my rule of thumb to say, 'Oh no, my pleasure' if they offer to pay on the first date — and maybe I’ll hint that you can get the second date or something like that.

"If they push a second time and say, 'No, no, no; I’d like to help,' I’ll split it because I don’t want to make it awkward. But interestingly, if they do push to split it, my gut reaction is that they must not want to see me again; and they don’t want to feel like they owe me anything.

"Again, I never expect anything of anyone. I didn’t think that was real — the whole guys expecting girls to drop their pants because they paid for dinner — until my female friends told me stories of guys expecting that, and my mind was blown. But even though I’m trying to be culturally evolved, I still have that initial thought — that a woman who wants to pay on a first date isn’t interested — because of the culture we live in."

What do you generally like to do on a first date? You did a lot of drink dates in this first week.

"I do generally like drinks. Alcohol is a great social lubricant; it kind of takes the edge off the awkwardness. I understand that not everyone participates in drinking culture, and I’m not talking about getting blacked out. A great first date is like, let’s go to a fun place — a bar neither of us has been to or one they’re comfortable with — and get a beer.

"I’ve had pushback from friends who say, 'Oh, we wish guys were more creative on the first date.' My argument is back to the inequality, especially with app life. There’s this expectation that guys are supposed to plan these amazingly elaborate and creative dates for people they’ve never met and don’t know that much about.

"The old model was getting to know someone through church, or through friends or family or whatever, so by the time you went on the first date, you already knew something about them to a fair extent. Now, you don’t know anything about them. The number of first dates I’ve gone on where you just don’t click? That’s fine, but if you’ve planned something elaborate, it would be such an exhaustive use of time and energy that I’d personally rather save for a second date."

Going into the details, you spent about $45 on Date #2 in this first week. Tell me about it.

"It was for cooking at my place and I was a little surprised they agreed since it was a second date. I tend to be very upfront: I’m not trying to take them to bed. I like my apartment, I like cooking, and I’m a good cook too, so to me, it’s more meaningful to have a meal in a relaxed, comfortable environment where we can talk more. There’s not the background noise of a bar; there’s not a show we have to pay attention to. If we want to watch TV, we can always pause it if we hit on an interesting topic."

It looks like she bought some of the groceries?

"She did. I realized at the grocery store that it was going to be very expensive and she happened to text me while I was there and ask what she could bring. Normally, I would say just a bottle of wine, but she works near a grocery store and doesn't eat meat, so I asked if she wanted to pick out the fish. That way, she could also feel like she contributed to the main course even though I was doing all the cooking."

How did that go over — you asking her to buy something?

"Well! She wanted to contribute and actually gave me a hard time that I wouldn’t let her help clean."

Do you have any financial considerations based on the number of people you date at one time? Because you had several first and repeat dates this week.

"Time tends to be more of the constraining factor than money. If I’m feeling tight on money, which I usually am, then I might go on less expensive dates: meeting up in the park and drinking wine. I try to avoid dinners, especially on first dates, because it’s New York City and I just couldn’t afford to do that often. But I try not to let the economic control things."

You still like to cook for your dates. Does one really feel less expensive?

"Eating in is a little less expensive, but way higher-quality in terms of time spent. It’s more effort on my part for sure, but I think it's evident that I’m investing more time because I like them. Anyone can go out to a restaurant. I guess it’s one way I try to differentiate myself from the finance bros.

"I hear stories from a lot of my female friends who go on dates with these guys for $200, $300 dinners, easy. I simply can’t afford that, and I can’t compete with that. If a girl is looking for that as one of her top criteria, I’m not sure she and I would have that much in common. Certainly, people I’m dating are dating other people and it’s not a competition, but [cooking] is my way of trying to let them know that rather than spending a ton of money, I’m putting in a lot of effort and thought."

Date #6 was a third date with someone at the movies. Was that the same person as the dinner at your apartment, and how did you decide on a movie?

"It was the same person! I saw them twice in one week and things are going well. The limiting factor is really their schedule. They were seeing multiple people — and still are — so their social calendar was full.

"In New York City, going to the movies is certainly more expensive. On that date, I bought the tickets, snacks, and food later; she paid for dessert. But I try to look at going to movies as being more than just the movie. For instance, this person doesn’t know it yet but I bought us tickets for Star Wars. She’s a big Star Wars person, and I like Star Wars. The show is on my birthday, so I’m pretty sure I’ll be able to convince her to hang out with me that day."
In Week 2, on a first date with someone (Date #7), she paid the $3 tip. Was she insistent on paying that?

"I don't quite remember, but I can totally imagine someone saying, ‘Oh, let me pay,’ and then me saying, 'Well, how about you get the tip?' What’s more common is that if I’m having a good time and they are too, I’ll say, ‘How about I get this, and you get ice cream?’ Or, ‘Why don’t we get drinks after and you can get those?’

What about Date #8? It's another date where you spent a little more than usual, and she paid some.

"This is another person I’m seeing regularly, and it was a second date. She's super fun and makes a little more money than I do … I hope it’s not misogynistic, but I feel a little awkward about them paying for things. I just don’t want them to be paying because they think I can't afford it. I guess I have trouble letting people pay too much for me."

Do you feel that way in general, or just with women you’re dating?

"In general, but let me rephrase that: I have trouble letting people spontaneously pay for everything. For instance, I had my board exams over the summer and one of my friends asked to take me out to a nice dinner to celebrate. I said that would be amazing. We went out, it was an expensive dinner at a steakhouse, they paid for everything, and I was totally fine with that. I think they enjoyed paying for me, they make plenty of money, and we kind of set it up in advance. Where I have trouble is if we go out to eat, it’s expensive, and then at the end, the other person's steals [the bill] — which is what happened with one of the women I'm seeing."

How did that happen?

"I went to the bathroom and [when I came back], the server came up and said 'Oh, your bill is all paid.' That’s harder because there isn’t a conversation. I feel uncomfortable about that."

Do you ever steal the bill?

"Only with people who have done it to me. If they do it to me, then I know this is going to be an issue. It’s like escalation of arms — earlier and earlier. I’m just waiting for the day where she’s called ahead to the restaurant and given them her credit card before we even get there. I know that’s going to happen.

"Then, the person I’ve been seeing most frequently pulled a Girl Code on me one time. The waitress wouldn’t come back to the table; she was like, 'Sorry, bro. Girl Code.' Literally two days later, it was a guy waiter and he wouldn’t bring it either! That time I actually brought it up with her. I said, 'You know, I really appreciate it but I’m a little upset because I wanted to buy dinner for you. I invited you out and you didn’t give me the opportunity to even discuss it; you just paid.' I don’t want to sound unappreciative — I appreciate it. I just wish it had been a conversation."

What do you find is so important about having a conversation? You’re saying that payment is a gesture of showing someone that you want to take them out and treat them, but you also worry that you’re perceived as not being able to afford it?

"It’s not so much the latter; I think everyone I date is clear on the fact that I don’t have a lot of money right now. I won’t always be that way, so I don’t have any insecurities about women making more money than me. I think that’s great. It’s more about [the fact that] I asked you out. I picked the place. I was treating you. I was trying to take care of you.

"I can see that it sounds like I’m worried about them thinking I can’t pay for it, but that’s not the root cause. The root cause is that I invited them out, I wanted to treat them, and if they said in advance, 'Hey, I want to treat you. I want to take you out and I’m going to pay for everything,' I would have been fine. It’s more that I kind of feel like they stole the thunder. I initiated the date and picked the place, and at the last minute, they swooped in and were like, 'Ah! I took care of it!'"

On that note, can you tell me about Date #10?

"Yes, this was one of the bill stealers; it was a fifth date and she paid for everything. I think both women who do this are very giving. They want to treat, and this is their way of showing they care maybe. But this one was frustrating because we were actually having brunch with two friends of mine I wanted her to meet, and she stole the whole bill."

Do you know why she does this?

"I think we had a conversation about it after brunch. I didn’t bring it up immediately; I talked about it with some other friends and asked them what they thought in case I was being weird. I don’t want to put too many words in her mouth, but my conceptualization of her thoughts and actions is that she’s an independent, confident woman who’s got a good job, has money, and she can afford it. I think her thought is, I can afford it. Why not treat you and your friends?

"My friends loved it. They were like, ‘You can bring this girl around any time!' It was just awkward to me because they were my friends. If it had been her friends, I would have thought it was fine. But again, it was the same thing: I invited you. I specifically wanted to introduce you to my friends and bring you a little bit deeper into my world, and then you swoop in. It’s not that I don’t appreciate it; it just seemed to be kind of usurping [the moment] somehow."
So, this week, there were two first dates, and you paid a lot more than you usually do for a first date. What was different?

"One of them with somebody I already knew for a couple of years. Before we went out, I was pretty sure it was a date and afterwards I definitely knew, but it was a little ambiguous at first. They picked the restaurant and it ended up being expensive. I reached for the bill and they didn’t stop me; and when we got drinks after, they also didn’t stop me [from paying]."

Why was this date so much more ambiguous, especially since you say you tend to be a more upfront person? That clarity seems to have a lot to do with the price differentiation.

"I think I was willing to spend a lot more money on them because I knew them already. It was an amazing night; the whole night was wonderful. It was expensive but I didn’t mind as much. I’d hung out with them previously — not on dates — and we always had a great time. I knew what I was getting into and was willing to spend more money on something I knew would be great, and it was."
Tell me about this week, in which you went on much fewer dates.

"There were a few meh first dates, but most of these were repeat dates with the people I continue to see most. As the month concluded, I started seeing fewer people more often. I don't know if I'm spending less money now [because of that], but that trend of doing fewer first dates and more non-first dates has continued since then. The two people I saw most during this month, I'm still seeing them regularly. That's also part of my approach to dating though, which is fairly non-traditional."

In what way?

"I hate using labels because terms like polyamory come with so much baggage that the listener forms a preconception of you. I most commonly say non-monogamy; the term I see most often on the internet is 'ethical non-monogamy'. I don't use that because I don't think a lot of people run around saying, 'I practice unethical non-monogamy!' Those are just douches who are misogynistic and mistreating women — and probably some women mistreating men. But as someone who is non-monogamous, I firmly believe it's more than acceptable to see multiple people, and that it doesn't reduce the value of that time.

"The way I approach it is that if I'm seeing someone and I want them to be happy, it feels strange to try and control what they're doing when they're not with me. One of the characteristics that I value a lot in both people I'm seeing is that I can't tell you what their phones look like. They're not on their phones when they're with me; they're present in the moment. When they're not with me, I don't know what they're doing. I know they're with other people and I'll ask, 'Oh, how'd your date go?' — and different people are comfortable sharing different levels of detail. For me to say they can't go on dates with other people would be a form of control.

"But this is all above-board. I lose a lot of interest from people. A lot of people I meet online want nothing to do with me because I'm very transparent and upfront about my approach to dating."
Overall, you spent $1,264 this month. I know you were surprised by that number when we tallied it up, so how do you feel about it?

"I feel a little self-conscious; it sounds like a lot of money to me. Granted, maybe there are some guys out there who spend that much on four dates — or two dates, I don’t know — but for me and the means I have at my disposal, that seems like a lot of resources to be putting into something.

"There’s a little bit of self-denial going on. I know I’m spending a fair amount on it and I probably don’t keep track of it on a granular level because I don’t truly want to know how much I’m spending. Because if I did know, I might feel self-conscious and then curb it."

Have you talked to your friends about how much they spend on dating?

"No, they don't keep track. And honestly, I have a lot more female friends than male, and they tell me how they don't spend any money on dates. They go to bars and they don't buy drinks. When they do go on dates, the guys pay for everything, so I don't think they spend very much in general."

Hearing that number, do you think dating as much, or spending as much money is something you'll continue doing? The expensive dates were ones you really enjoyed. Do you think you'll approach dating differently now, or stick to the same thing because the results were worth it?

"I'm seeing, for the most part, two people now, and I'm probably collectively seeing them less often than my friends who are exclusively dating one person but seeing them four or five times a week. Between the two of them, I'm probably seeing them a combined three times a week. Maybe we're doing more things, but I like that. I don't necessarily want to sit around and eat Chipotle. Where I think it can have a financial impact is when I go on first dates with other [new] people."

Having done this exercise, Keep The Receipts, what do you think now about the culture of money and dating?

"I think that the financial aspects of dating are in as much need of an update as other aspects of dating, and the way in which our culture views dating. I think the general culture of dating is rather unhealthy in this country and very antiquated, and I think that finances are no exception to that. There are still really strong cultural expectations that are gender-based, specifically, when it comes to dating.

"That being said, I think to a great extent it’s self-selecting. You can find people out there who are going to agree with you whether you believe that dating is great as is, and the gender expectations are acceptable; you can also find people who think it’s unacceptable and want it to be revamped. Where you can make it difficult for yourself is if you refuse to even engage in the finances of dating and say the system is broken — which I think it is. But I also think you shut yourself off from the opportunity to meet people who might agree with you, if you don't give them a chance."
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