I'm A Sugar Baby—& I Expect A Gift On EVERY First Date

Illustrated by Abbie Winters.
In the past few months, we've chatted with sugar babies making anywhere from $3,000 to $12,000 a month. Some view sites like Seeking Arrangement or Arrangement.com as extensions of online dating — with a few more benefits. Others, however, treat their dates as work; their sugar daddies are like clients.
In our fifth interview with a sugar baby, we meet a 26-year-old New Yorker who only goes on first dates if a gift is promised, and once received $20,000 to discuss books on the phone. Read her full interview below, and if you have any questions, leave a comment below (politely, please) and she might just answer them.
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How did you get your start?
"I started sugar babying when I was between jobs. I was just at home watching Netflix, and I saw this documentary about sugar babies and their lifestyle. This one girl said she received $3,000 to go on a date. Since I was unemployed, and I wasn't sure where I was going, I created an account. At first, I treated it like a normal dating site. I had pictures with my face and everything. Then I learned that you shouldn’t so transparent about who you are — of course. Someone I knew found me on the site and told me I needed to hide myself, and my heart just dropped. I was like, 'Oh my god, oh my god, what was I thinking?'
"So I got completely off the site, but I had given my number out to one guy before that, and we dated for four months. It was very tumultuous. He was married, and he loved the idea of having this affair, and I fell into the whole gimmick. I didn't know better. He gave me a credit card, and I had a certain amount to spend on it. We would go shopping, and we were supposed to go to Paris together, and I was like, Oh my gosh, I'm getting $5,000 a month. He was spinning me in this web."
When did you get back on the site?
"After that relationship ended. At first, I was against dating a married man, but a lot of them are married. The ones you might have things in common with, or the ones you would be attracted to, they're married. I can think of a few who were well-known bachelors in the city, and they liked the site because the girls on the site aren’t nearly as clingy — they want someone they can go on a beautiful date, go shopping, have this amazing fun time, but if they never text you again you won't bother them."
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At my peak, I was making around $10,000 a month, sometimes up to $15,000 or $16,000 a month.

How much have you made on Seeking Arrangement?
"I stopped doing Seeking Arrangement for a little while, so I haven't made a lot recently. At my peak, I was making around $10,000 a month, sometimes up to $15,000 or $16,000 a month. Still, I'm super frugal. I might have YSL shoes and Louboutins, but I live in an apartment with roommates, and I just put away a lot of the money I've made because I want to go back to grad school. I'm still deciding exactly what I want to do, and in the interim, I've really been able to save a lot of money. When I get $5,000, the first thing I do is go to the bank and put all the money away."

Do you pay taxes on it?
"From what I've Googled and talking with my accountant, it seems like as long as the money is a gift, and it's under $10,000, it's tax-free. I ideally don't want to get audited, but they're just gifts. It's not like I worked for someone, and they're paying me — and these guys aren't paying me through their work or anything like that. I guess people can be mad that I don't pay taxes on it, but at the same time, when someone gives you a birthday gift that's a $200 gift card, or $200 in cash, do you think, Oh, I need to claim this? For me, it's just a gift for my time, or they just want to help me out, or it's an actual gift that they're buying for me."

Tell me about your first date.
"It wasn’t a good experience. I was really nervous so I ended up having a mixed drink before meeting this guy for tea in the afternoon. I wanted to be a bit tipsy. I showed up, and he went over everything. He wanted an arrangement where he would pay $5,000 a month to see me twice a month. It felt like we were talking about clients at my company, only the company was me. He said, 'Oh, you seem wonderful. I'm also talking to this girl from NYU, and I think she would be great, but you’re so beautiful. Let’s see if we can go somewhere a little more private and kiss to see if there’s chemistry.'

"Now today, I would never do that. I wouldn’t even meet this kind of guy. But he kissed me and he tried to touch me, so I immediately pushed him away and left. I felt it was inappropriate, and the whole night I was thinking, Do I want this kind of arrangement with him? And the next day, he comes back and says, 'I'm sorry, the NYU girl is the right person to pursue this with. I wish you the best.' I remember being hurt by it, and thinking, Shoot, I thought he liked me, I thought this would be something. Come to find out months later he sends the same thing to me under a new profile."
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Maybe I've lost out on great guys, but I won't meet someone unless they have some type of gift.

After that bad experience, did you change the way you meet up with men?
"I have a few rules. I won't meet someone unless they offer some type of gift. And, of course, I only meet them in a public place. Some girls don't have these rules, and more power to them, and maybe I've lost out on great guys. My view is, Hey, you’re supposed to be a wealthy person, you’re supposed to be serious about this. If you’re not willing to give me taxi money or something like that, then you’re not that serious."

How do you get them to agree to that?
"I have a thing that I say that shows that I’m really serious, and I basically put the ball in their court. I say, 'I'm happy to meet, but I have a very serious job. I can't waste time. I would appreciate a gift to show sincerity.' The ones who say no, I don’t see. The ones who say yes, and I like them, then I will see."

How has the gifts rule affected your dates?
"I've been able to find really generous men. I know it sounds crazy, but some guys do want to sit down with you and have a drink and give you $1,000. And it's just a gift to meet — absolutely nothing else. I've been on so many dates where if they're willing to give a gift, I'll go and meet them anywhere because it's free money.

"Then, I see how I feel, and hear what kind of arrangement they're thinking about. Maybe we'll go on a second date, and there will be dinner, and sometimes it will be followed by something more intimate. I treat it like normal dating at that point — see how I feel, see what I'm comfortable with. At the end of the day, the guys I want to have an arrangement with are the ones who are looking for chemistry. They're not looking for one 'wham bam thank you.' They actually want to get to know me. There are some people I have true chemistry with, and other ones, it's like, Thank you so much for the gift. I really appreciated meeting you. And I don't talk to them again. And sometimes, the guys don't reach out afterwards."
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The worst was $50. The best was $2,000 and a pair of Louboutins.

What have you gotten as a gift on the first date?
"The worst was $50. The best was $2,000 and a pair of Louboutins."

Wait, how did that happen?
"Basically, I suggested we meet at a cafe which was inside an expensive department store. After we met I said, 'Oh, I want to look at this pair of shoes.' And before I know it, boom, he pulled out his credit card. I was like, Yay this plan worked."

Is there anything you do before you meet your sugar daddies in real life?
"Before I meet them I try to find out who they are. I use a few apps, like Truecaller, or I'll Google a number to find out who a person is. If I can’t find that out I’ll ask more questions. To be honest I've never run into a serious issue with someone. I get a lot of messages so I go through and see which ones seem promising. The ones that don't seem promising, I just block them."

How many dates do you go on a week?
"I go on anywhere from three to 10 dates a week. It’s usually in the evenings when I'm done with work, and I keep them all straight in my calendar. I've had days when I've gone on five dates in a row — one date to the next to the next. Usually I'll just be meeting people for a drink. It sort of becomes a job, but if you know how to do this correctly it can be lucrative when you're young. It's about youth and beauty and intelligence — a lot of these guys went to Harvard or Yale or Stanford, and you have to be intelligent because if not, they might want to sleep with you, but they won't want anything long term."
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Before this, I never had a pair of Louboutins... and here I am now, with five pairs of Louboutins.

Why do you think these guys are on Seeking Arrangement?
"I've had an arrangement with a guy who just liked the idea of it. He's someone who likes to give gifts, and he liked the idea of having a special gift for me every time we saw each other. He thought it was more fun and less serious than dating. So with him, it felt like meeting a guy from OkCupid or something, except I got an awesome gift like a YSL bag every time I hung out with him.

"For the older guys, I think it's a mix. Some of them really want companionship. They just want a pretty girl to hang out with and talk to. They feel like they're helping you out with school and work and a future. Then there are the ones who are married, and they want a younger version of their wives, which sounds kind of weird. But some of them get so nostalgic about their earlier dates."

Why are you on Seeking Arrangement?
"I mean, the money. And, I don't know. I love it. I've been able to travel a lot — I've been to Europe, Miami, Vegas. I have met some really prominent people on that site, and I've been able to meet some really cool people and have amazing stories to share with my friends. Before this, I never had a pair of Louboutins. I never had a pair of Valentinos or Ferragamos, and here I am now, with five pairs of Louboutins. It’s fun to have those things when you’re young and living in New York."
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With this type of dating, it's the same exact guy, and at least in this case they pay my rent for three months.

Do you go on any normal dates?
"I'm still on normal dating sites like Bumble and OkCupid and Match. But I was dating these hedge fund Harvard, 32-year-old guys, hoping they would want something serious, but they just wanted to have fun. You date, hook up, and never hear from them. With this type of dating, it's the same exact guy who just wants to have fun, and at least in this case they pay my rent for three months.

"Obviously that's not every guy on there. There are also a lot of wealthy guys who are just lonely, and they want a girl to come over and cuddle. I know people are going to think that's a lie, but it's happened to me."

Have you ever stepped away from sugar dating?
"Around November, I started getting busy with my salaried job, and I kept finding 'salt,' or guys that were salty or fake. Salt looks just like sugar but doesn't taste like sugar — so these are guys who are pretending to be sugar daddies. But I can figure it out by talking to them for a minute. I ran into a lot of that in November, and I wasn't making the kind of money I was making before. So I got off the site and didn't use it as much, but then all of a sudden work slowed down, and boom, I'm back on the site. It's just like, you're looking at your cool items, and the things you have, and you're looking at your bank account, and you just think, Hmmm, I could go on a few more dates and change this situation. It's hard to stay away from free money.

"But the cost is that it's stalling me. It's time-consuming. You have to go on the site, send text messages, see if they're legit, and that takes up time. Plus, a lot of them have drama. They all say, 'I'm not looking for a girl with drama,' but they are the ones that have a ton of drama and you have to deal with that.

"There are also times when you're more intimate with somebody, and you're like, did I do that because of the money? Or did I do that because I actually like this person? Luckily whenever I've started to feel uncomfortable, I've been able to get out of that situation."

How often do you check in on how you're feeling?
"I’m constantly checking in all the time. When you push your limits, you start to think, Are you crossing the line? And I’ve told myself from the beginning that if I ever feel like I've gone too far, then I'm done."
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You need to remember that your time is the one thing you can't get back.

What’s the best sugar daddy experience you’ve had?
"There was a man I'd never met who sent me $20,000 over the course of four months. He sent me books in the mail and we would discuss the books. He just liked the whole mentor aspect. So I was his online sugar baby. Eventually he found someone who was close to where he lived, and that was the end of that. But obviously, he was a super generous, and a really nice guy. Definitely my favorite."

Looking back, what would you tell your younger self before she started sugar dating?
"It sounds so glamorous and yes, my experiences have been glamorous. It’s nice to eat at Daniel and Per Se and have the gifts and the money. But the one thing you have to realize, whatever these guys are doing, they're paying for your time, and you need to remember that your time is the one thing you can't get back.

"You want to make sure you have your feet firmly on the ground and know what you want to do. Because I have lost myself along this way. There were six months when I wasn't serious about anything. I was just making money and not really doing anything. I wasn't focusing on if I want to go to grad school. And a lot of these guys will say they want to be your mentor and in some cases that’s happened, but for the most part it’s all talk and it never becomes anything. You meet them and you think, I’m going to be the next whatever. But they never really help you."

This interview has been edited and condensed for clarity. Have questions? Leave a (polite) comment below and she might just answer them. Have a story you'd like to share? Email us here.
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appearance by Laura Delarato.
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