I'm A Former Sugar Baby — This Is Why I Stopped

In parts one and two of our interviews with sugar babies, we chatted with a woman who views the scene as a job, and another who looks at it as a serious relationship. Both parties, however, differentiated what they do from sex work — a view much contested in the comments.

For our third interview, we talked with Lily, a 25-year-old in New York City who dabbled in sugar dating on and off for three years. Ahead, she spills everything — including how much she charged per date, and why she ultimately left the scene.

This interview is part three of our series about sugar babies. It has been edited and condensed for clarity. Names have been changed. Have a story you'd like to share? Email us here.

Tell me about yourself — what were you doing when you decided to try sugar dating?

"I graduated from school in 2014, and after that I moved back home and started working at a designer shoe store downtown. I was making $12 an hour plus commission. When I started, I had hoped a lot of people would come in and spend a lot of money, but in reality it was really slow most of the time. I was probably just getting $400 a week or so.

"I really wanted to move out of my parents’ place, though, so when I met a girl who was on SeekingArrangement.com, and she told me how she had a lot of extra cushion, I decided to move out and joined."

"I’ve always kind of liked older men, and I have a fantasy of being with a much older guy, so it didn’t really scare me that much sexually."

What types of messages did you get when you were on the site?

"I got all sorts of guys. I got a guy with a foot fetish who wrote a long paragraph asking me to send him my dirty socks. He told me he would pay for my socks and buy me new socks in exchange. He offered me like $10 for my socks. I didn’t reply, because it wasn’t something I was willing to go to the post office for, but it was an icebreaker for when I met other people.

"I also got long paragraphs from guys explaining who they were and what their situation was — if they were married, why they were on the site, stating exactly what they were willing to pay, exactly what they were expecting. I was seeing anywhere from $300 to $2,000 a date, and probably all of them were expecting sex. Then there were also messages like, ‘Hey what’s up.’ I was more inclined to respond to someone who wrote a custom note, though.

"A lot of them were married, but that was a deal breaker for me. I’m all for open relationships, but I don’t feel comfortable being a part of something a guy is keeping from his wife."

Were you nervous about meeting the men off the site?

"I’ve always kind of liked older men, and I have a fantasy of being with a much older guy, so it didn’t really scare me that much sexually. I was more scared of meeting strangers, and I was scared of my family and friends finding out about it. A lot of people use fake names, so there’s no real way to verify them. I would always exchange messages with them for a day or two, and then I would figure out if they gave me a Google Voice number or not. If they gave me a fake number, then I wouldn’t give them my real number, because there wasn’t any mutual trust involved. I’d also require a picture before meeting.

"For first dates, I always made sure I was meeting people in a public place. I was definitely nervous about the first few dates, and the very first one I went on was kind of strange. I met him at a hotel bar lobby after I went on an interview for a corporate job. We got a drink at the Hyatt next to Grand Central, and we just talked about what I wanted to do with my career. He was very normal, nothing to write home about, and nothing to be scared of. But it was a little awkward, and I think he could feel it, too. He gave me $200 in 'cab money,' quote, unquote, but after that I didn’t hear from him."

"I asked him if he was married, and he said, 'Are you going to hate me if I tell you the truth?' And I was like, well, that tells me the truth."

Can you tell me about your first arrangement?

"I first met him for a drink at Rockefeller Center, and we hit it off. I don’t like talking about arrangements face-to-face, because it’s uncomfortable for me, so we had a normal date, and he gave me $50 after the date — actual cab money. We then texted about it afterward to discuss what the terms would be. He asked me what I was expecting, and I said I would probably want around $1,000 per date. I had read blogs and Googled it, and he said okay. I thought I had given him too low a number. But we agreed on that, and I started meeting up with him every other week or so at a hotel to sleep with him, and he would give me $1,000.

"He was completely normal personality-wise and not creepy. He lived in Westchester but slept in the city a lot because of work. In the end, I cut it off because he told me he was married. He told me he wasn’t married in the beginning, but he was so discreet. Like, I didn't like being seen in public with the guys from Seeking Arrangement, but he was more secretive than I was. I was 22, he was maybe 42, and if we had been seen together it wouldn’t have been the end of the world, but he acted like it would be. So I asked him if he was married, and he said, 'Are you going to hate me if I tell you the truth?' And I was like, well, that tells me the truth.

"That was me realizing why he was normal. I’ve come to learn that most of the socially normal ones are married."

Tell me about the other men you met.

"There was another guy who I sort of developed feelings for. He was a film producer, and he was bi-coastal, around 40. It was very, very natural for us, and after a while I asked him to stop giving me money because it felt weird. It felt like he was my real friend, and we even went away a couple of times together. But he kind of ghosted me, and I haven’t heard from him in a year.

"There were also just a lot of people who wouldn’t give you a real name, and you couldn’t really track them down. One time, this guy I met over coffee Ubered me to his apartment. He told me he was going to give me $2,000, and that he had some weird PayPal account. I gave him my email but never got the money. I felt completely used and humiliated, and I texted him like 500 times afterwards. This was a younger guy, too — so I kept wondering, 'Why couldn’t you just go out and find a girlfriend?' That was the one time I felt really stupid."

That's horrible. Was this early on?

"Yeah, it was early on, and that was the only time it happened. I never accepted PayPal again — it was just cash that was the safest. And no later payments."

It seems like you view this more as sex work than the other sugar babies. Is that true?

"I would agree that this is sex work. I’m not against sex work — I think it should be legal. And yes, sites like Seeking Arrangement could empower sex workers, because they can choose their own clients and decide how far they want to go. But in general, sex work would be safer if these men couldn’t be so anonymous."

"There was one guy who gave me $25,000 and I only met him three times ever."

How much have you made off the platform?

"I made over $100,000 in the three years I was doing it on and off. After getting on Seeking Arrangement, I quit my retail job and focused just on that for two months. I was making around $12,000 a month.

"In addition to that, there was one guy who gave me $25,000, and I only met him three times ever. But he gave it to me all at once in three separate bank transfers. It’s crazy. I met him when I was working at the shoe store. We got a drink at a hotel bar, then we had a date at a hotel and we had sex, and he gave me $1,500. After that, we were just texting, and I told him how I really wanted to leave my job, but I couldn't find a way out because my confidence was low, and I had no money — even though I did, I was just spending it all. He was like, 'Okay, I’ll give you a break. I’ll take care of you until you find out what you want to do in life. How about I give you $25,000? Would that be okay for you to take a couple months off?'

"So he transferred me the money, and we met up two times after that, and we never met up again. I know it sounds unbelievable — it was the least amount of work I’ve ever had to do. I Googled him, and he’s a billionaire or something, which makes sense. He didn’t seem to really care at all.

"That was the time when I started shopping like crazy."

"I liked the feeling of going into a store and being able to buy whatever I wanted. I used to have daydreams about that as a kid."

How did sugar babying affect your spending habits?

"Growing up, I was never poor. I grew up in an upper middle class family, but my parents were always strict with me, and I had a jealousy problem with my friends who had more than I did. When I finally had all this money, I just went to Saks and Barneys and spent thousands of dollars, because I had a job that was paying me a base salary, and then I was making money on top of it. So I would just spend it all. I liked the feeling of going into a store and being able to buy whatever I wanted. I used to have daydreams about that as a kid.

What you would buy?

"I got a Chanel Boy Bag, and that was like $5,200. I have a YSL bag, some really nice shoes and clothes that I don’t wear. I would just go shopping and feel this high. I'd get stuff I didn’t need, and it would end up sitting in my closet.

"I did have a desire to stop, though. I wanted to stop. I decided to start looking for a new job, and someone told me to make sure my social media was okay before I started looking. But instead of worrying about social media, I was more worried about Seeking Arrangement. So I decided to make a guy’s profile, just to see if I could find myself, and it was really scary because I found myself right away. I couldn’t have messaged myself, but I could see everyone — I even recognized one or two people I’ve met in real life. It was alarming. So then I deleted my profile, and I’m still not on it."

"I’m not going to cushion it anymore — I’ve realized that I don’t really need that cushion."

Did you have trouble adjusting to life after Seeking Arrangement?

"When I stopped using the site, it was a sudden change in lifestyle, and I didn’t really know how to stop shopping. I didn’t save any of the money, either — I had a couple thousand saved but that went away quickly.

I’ve definitely managed my shopping a little more since then. I’m much more careful when I’m making these purchases, though. I guess I have more a conscience when I’m shopping for anything that is outside my price range because I know that money is not going to be replaced until my next paycheck comes. But I’m not going to cushion it anymore — I’ve realized that I don’t really need that cushion, even though I'm not saving anything."

What was the most expensive thing you bought recently?

"I haven’t spent more than $400 or $500 on a single item in a year. The nicest thing I bought recently was a pair of Chloe shoes, and even though I wasn’t actually in a place to buy them financially, and I probably shouldn’t have, it felt good that they were mine. Like, truly mine."

Truly yours? Did it feel different when you were shopping with Seeking Arrangement money?

"When I was on Seeking Arrangement, I could throw money in the air, and it wouldn’t matter because I could just make it back. But it feels better now when I buy things for myself because I don’t have to think about how I was able to buy them. Sometimes, when I was on Seeking Arrangement, I would think to myself, 'If this salesperson ever knew how I got this money...' It would make me feel really shitty about myself afterwards. Buying those things felt really good when it happened, but now when I look at that Chanel bag, I just think of all these men."

"[Sugar dating] makes you feel like you need a guy to push you further in your career when you could really probably do it yourself."

It sounds like you regret doing it.

"I do feel regret. I needed to find a passion on my own and succeed independently, and I feel like I lost sight of that over the past few years, because it steered me away from my career goal. Like, sometimes, you believed that these sugar daddies were being a mentor and really trying to help you. But all these men were just objectifying you."

What do you mean?

"I went on a couple dates with this guy who was very into being a mentor, and loved giving interview advice. We didn’t do anything sexual, and he kept saying he would introduce me to this person and this person and this person, saying he would get me a job. But he never followed through with any of the connections. It made the whole thing feel phony to me, and it can bring down your confidence a little bit. It makes you feel like you need a guy to push you further in your career when you could really probably do it yourself.

"Like, they’re good at giving interview advice, but nobody is really going to save me, and I shouldn’t think that they’re going to."

Do you wish you had done anything differently?

"If I could talk to myself back then, I would tell her to do it, but when she gets $25,000 to save it, get a job right away, and not be a crazy spending person. Do it for a very brief period of time, and then stop right away.

"I have this secret now that I’m bottling up a little bit, and I wish I had gone about life the normal way. Not the normal way, but just in a way that empowered me a little bit more. I feel like I gave up on my career so early — I wanted to work in fashion — just because I was working in retail after graduation. I don't know why I gave up on that so quickly."