"You feel more confident knowing that someone is going to be like, 'Hey I’m going to pay for your apartment.'"
"The biggest difference with Tinder is that it’s so much easier to tell people how you met your date. Like, Hey I met this girl on Tinder and I took her out. But that changes drastically when you meet someone on Arrangement.
"I also think in general, with the girls I’ve dated in the past, you go on the first date and you don’t expect a ton from it. You play this game where you put your best foot forward, and you look at how everything goes and reassess after that. When you’re going on an Arrangement date, it’s like, something could potentially happen here. You feel more confident knowing that someone is going to be like, 'Hey I’m going to pay for your apartment.'"
"I actually did offer to pay for the bill, which looking back, didn't make sense."
"In the past I've always paid for everything on dates — drinks and dinner. So this is a completely opposite approach for me.
"I don’t feel like every person I date going forward is going to have to pay for me, and I've definitely felt weird sometimes. I have gotten more comfortable with the arrangement at this point, but I understand how it looks from the outside."
Did you offer to pay on your first Seeking Arrangement date?
"I actually did offer to pay for the bill, which looking back, didn't make sense. She didn’t let me. Second one I got a little smarter. I did the wallet reach on both those dates, and I genuinely would have paid, but now I don’t even do the wallet reach anymore."
Tell me about your first date from the site.
"I didn’t really know what I was doing. It was like dinner and a drink, and that was really it, to be honest with you. Everyone always thinks there’s going to be more details, but they were just dates. The second date I had was with a different woman, and it was her first time using the site. And it was the same — dinner and drinks. Not too exciting as far as perks.
"I’ve only been on the platform for about a year — maybe 11 months. This is the third arrangement I’ve done, and sometimes I forget where I met her and how long it’s been going on."
"The first two times I slept with her, I felt a little different, but now I don’t feel weird about it at all."
"The woman I see is divorced with one kid and has a pretty good job. She works in tech, and she’s 46 — her birthday is actually next month.
"Right now she pays for my apartment in San Francisco, which is amazing — I live in the Marina right now — and a membership for my gym. I pay for a trainer and SoulCycle. My rent comes to $3,000 a month, which is so much more than it I paid in New York. And with the gym membership, she gives me around $3,300 a month. I’ve also been to Miami and Cancun with her, and we have one more vacation planned."
How did these terms come about?
"The rent was specifically an offer from her; she was the first one to throw that idea out there. I was talking about the biggest differences between New York and San Francisco, and I think there’s a perception they have similar housing costs, but they’re not. SF has a lot less inventory and much higher prices.
"Then the gym was a joke that turned into something that is now included. She pays me via Venmo. But with Venmo, you can only do $3,000 max, so she breaks it down into $2,500 and $750, or $800 the following week."
Do you sleep with her?
"Yes. The first two times I slept with her, I felt a little different, but now I don’t feel weird about it at all."
What was weird about it at first?
"I think it was knowing that someone had agreed to pay for my apartment, so there was that first thought of, Hey, is this really happening? It’s not the most common way of dating. So it was just going through the experience first time, mentally checking in at where I was with it. Does this make sense? Is this something I want to be involved in? And I really enjoyed it."
"It’s just someone paying for my rent. It’s not that crazy."
"The financial reward is definitely a bump for me. I’ve probably made around $30,000. It’s something I can use. I also do like her to a point. So I don’t know where that leaves me. Obviously, she’s paying for my apartment and my gym membership, and I have genuinely a good time with this woman. I like her. I think if you take out the financial gain from it, I would still want to see her. But I don’t know how that emotion or feeling would change if there wasn’t a financial gain as well."
Would you ever do the reverse? Be a sugar daddy?
"My immediate response is yes, but I don’t know how I would feel about paying for a 24-year-old’s apartment somewhere. That could drastically change, though. I have no problem looking into that.
"I really don’t think it’s any different from going on a regular dating platform. Yes, there’s a financial aspect to it, but honestly I’m not walking around with more money in my pocket. Instead of cash, it’s just someone paying for my rent. It’s not that crazy. It’s almost like a matching platform, where I want to find someone to date, but I also need help with something else."
"To be open with you, people can make some pretty big financial gains by seeing a few people at a time."
"I would definitely ask for vacation more. I would put that into the terms. It can be hard to find someone who has the time to take the vacation and the money to pay for it. I would take less rent in order to travel more. It’s always a good time, and I would love traveling to Barcelona, Cuba, Italy, or Southeast Asia."
But you're just seeing this one woman right now?
"You can make some pretty big financial gains by seeing a few people at a time, but I’d rather just see one. If it ends, I would try this route of dating again, especially while in school. I’ve always been a serial dater. I don’t think I would be on this platform to see multiple people. I’m just seeing where this is going right now."
Do you see this going somewhere more serious?
"I definitely am getting to a point where I see it as more than just a hookup. I don’t think I would say it's a full-blown relationship, because of the terms and things like that, but it’s more than just paying for something. I see her three times a week, but we haven’t had the deep-dive conversation. I expect she’s going on dates, and I’ve gone on a few dates, and we’ve made jokes about it. But we’ve never really sat down and said, 'Are you seeing other people right now?' I think we’ll probably have that conversation at some point."
Would you consider marrying someone you met on the platform?
"I can’t give you the best answer. These arrangements are still in the infancy of being socially accepted, so I have to really think about that. I have to really like the person.
"I’m just trying to think about how that conversation goes. Like, 'Hey, you don’t have to pay for my apartment anymore.' How would you have that conversation? If you’re personally gaining from the relationship, what is it like when you say, 'Okay, this is enough?'"