A lot of the men I went on dates with... they basically want to pay for play.
“I got back together with my boyfriend, and then we broke up again. I was like, All right these men are going to spoil me. I was 21, so I could drink, and I went back on Seeking Arrangement. But I never had an actual arrangement with anyone on that site, even though it was the site I went on the most.”
“We could never agree on an actual arrangement. A lot of the men I went on dates with, they didn’t want to give you a monthly allowance, which is weird because that’s an option on Seeking Arrangement. They basically want to pay for play. Give you money to have sex with you but on a continuous basis. A lot of girls do that, but it was just not something I wanted to do, which is fine. In those relationships, you don’t have to deal with the emotional part of having a sugar daddy. You can just be you and have multiple sugar daddies and live your life, but it wasn’t really what I wanted to do. I wanted a sugar daddy who was like a boyfriend.”
So how did you meet your first sugar daddy?
“It was actually another site where I met my first real sugar daddy — I think it was SugarDaddyForMe.com. He was younger than the first man, maybe in his late 30s, and he was a lot of fun. I wasn’t living in New York City at the time, so our first date he called me and said, ‘What do I have to do to get you to come into the city today?’ I told him he had to pay for my travel there and get me a hotel room in the city. Before I left my house, I told him, if I didn't like him, he wasn't staying with me. But he showed up, and he was very handsome and definitely my type. He was really fun. He loved to go out and hang out, and he was very carefree. That first night we slept in the same hotel room, but we didn’t have sex, and then he left very early in the morning, around 5 a.m. I didn’t even question it. We saw each other again three days later, and we just kept it up like a routine. We ended up having an arrangement for two years.”
What were the specifics of your arrangement?
“I’d see him twice a week. We were intimate, and he'd always transfer me money, but he didn’t want to. I would ask him for money for specific things like my nails, my hair, shopping, my phone bill, and he wouldn’t want to give me money. I’d say, 'We met on a sugar daddy site. You’re supposed to give me money.' So it was off and on — it was a cycle of us breaking up and getting back together, and having the same argument about money, and then breaking up and getting back together again. Every time, I would tell him, 'Okay, I’ll see you, but you know I’m going to want money.' And then he’d begrudgingly give me money. He probably gave me $500 every time I saw him, and we saw each other twice a week.”
They think... you should feel lucky that I’m willing to date you.
“I see this with a lot of younger sugar daddies. They feel as though they don’t have to give you money or gifts because they’re like, Well, I’m wealthy and young, and it’s either me or these older men on the site, and so you should feel lucky that I’m willing to date you. Mind you, they’re still 15 years older than I am, and married with a family, so there’s no future there. Really, I’m not benefitting from you taking me out on dates — men my age could take me out, too.”
Did you know that he was married when you started seeing him?
“He told me that he was single, and he had a daughter, and that he was still on good terms with the mother of his kid. But I started to put two and two together. Like, why are we always meeting at hotels and not at your house? Then I googled him, and on the website for his company it said that he was married, so after a couple of dates, I was like, 'You’re married, aren’t you? You totally lied.'
“So he was married, had a kid, but I also found out later that he had other sugar babies. Obviously, it wasn’t a monogamous arrangement, but that’s basically why we ended, because he didn’t have enough money to afford all of us anymore, and I was the last one he took on. But I liked the fact that he was young, and I wasn’t embarrassed to be seen with him in public.”
When did you realize he was also seeing other sugar babies?
“Maybe three months in. It made me upset, actually, which is really ironic, given the fact that he was married. I’m not going to sugarcoat it and say I was morally above dating a married man. There are very few real sugar daddies who aren’t married. The men who are paying you are paying you for discretion, basically, and they’re having this midlife crisis where they want to date young girls and relive their college days. Those are the best sugar daddies, to be honest, and he wasn’t the last one. But it’s like, this man, nothing makes him satisfied. Not his wife, not you. I definitely overanalyzed it a lot. But what can you do? You just have to focus on the money aspect of it.”
You do fight with your sugar daddy like you fight with your boyfriend.
“At the beginning, I didn’t because, I had this weird naive loyalty thing going on. After a while, though, I started seeing others, especially because we were breaking up all the time. So I went on other sites — some of the best sugar daddies I’ve had were from sites that aren’t specifically sugar daddy sites. Like misstravel.com, which was a site that’s for traveling together.
"That’s where I met my second guy, who was my longest arrangement. He lived in Florida and we Skyped a few times. On our first meeting, I made him travel to me and meet me in the city, and I had him book a suite at this hotel where I wanted to stay. It was the penthouse suite, and I showed up really late because I was out getting drunk with my friends. That was really shitty of me because he had flown in from Florida, but it was just funny. We got along pretty well, and we lasted three years. We had sex that first night and discussed our arrangement and a trip to see him, and then he gave me $1,200. I went to bed, and he was gone when I woke up in the morning.”
What was that arrangement like?
“I didn’t see him that often, but we talked on the phone all the time. He flew me out to Florida maybe once every two months, or if he had time, twice a month, and he would always send me money first before I left home. I would stay with him at his apartment for a few days at a time, and even if I didn’t see him for a month or two he would send me between $300 and $800 a week, depending on what my needs were at the time.
"We did break up a lot, though, so we’d end up arguing, and I wouldn’t see him for maybe three months. Then he would email me or something because I had blocked him, and he’d say, 'Oh I miss you so much, blah blah blah,' and I was probably strapped for cash so I would go down and see him again.”
Tell me about your fights — were they primarily about money?
“You do fight with your sugar daddy like you fight with your boyfriend, but every single fight I’ve ever had with a sugar daddy was about money. It was always about money. They get to a point where they feel like we’re so deep into a relationship they shouldn’t have to give me money anymore, but I think the opposite. If you care about me, you’d want to take care of me. And the thing is, they don’t want a real relationship, either. He never would have moved me out to Florida with him. He wanted me to remain monogamous, but he didn’t want the actual commitment of a relationship. They wanted me to be fully-committed and in love, but they didn’t want that for their side. They all think they’ve been paying me and taking care of me, so I owe them. It was always the same argument with them.
"I think they also realize that this is not real. For a while, they can pretend that this young, beautiful girl really likes them for who they are, but then they want proof.”
How long were you in this cycle?
“I’d break up with one of these two guys and get back together with the other. I would just go back and forth between both of them for two years straight, and it was my only source of income at the time. Then I actually became what you would call a ‘Spoiled Girlfriend.’”
There’s a very thin line between being an escort and being a sugar baby.
“There are these weird levels of sugar babies. A spoiled girlfriend is when you’re basically in a real relationship with an older man who takes care of you. He’s your boyfriend; you’re going to meet each other’s families and friends and colleagues.
“There’s the spoiled girlfriend, the regular sugar baby, and rinsers. Rinsers are girls who give men the expectation that they’re going to have sex with them, get everything they can out of the guys, and ghost them. I never do it, because it’s almost like scamming. I feel like it’s dangerous — you don’t know what these men are capable of when they’re angry, but rinsing is a very popular thing.
“Then there’s escorting. There’s a very thin line between being an escort and being a sugar baby. A lot of sugar babies have this idea that they’re better than escorts, and they’re not doing the same thing, but I think it’s because a lot of them do a lot of rinsing”
Do you think sugar babies are different from escorts?
“I think sugar babies try to differentiate themselves from escorts because they have the emotional connection to their sugar daddies and that's the only difference between being an escort and being a sugar baby. With an escort it’s more straightforward. You have an hourly rate, and this is what you can and can’t do. But they do have repeat clients... so it’s kind of like with a sugar daddy. I guess sugar babies think just because they are more public that it’s not the same thing. They think they’re at a higher level than escorts when that’s really not the case. Sugar babies and escorts and strippers and, even in some cases, models, we all fall into the same category. We’re all sex workers. There’s no hierarchy. That’s something I want to make clear. I feel like maybe people are in denial and not wanting to admit it to themselves, but it’s like, these men are literally paying to have sex with you.”
After five dates when he asked me to be monogamous with him... I said okay, but I want you to consider giving me an allowance.
“A month after I broke up with the young sugar daddy, I ended up going on Tinder and just swiping right on older men. I swiped right on this doctor who Super Liked me, and at the time I didn’t have any sugar expectations of the relationship. I figured I'd go on a date with him and if anything, maybe I’d get a nose job out of it or something like that. Maybe he would give me a discount, or his colleagues could do some type of Botox. But on the first date, he kept telling me that he wanted to take care of me, and I was like, Does he want a sugar relationship?
“He didn’t give me money for our first few dates — and I didn’t ask him for money — but he just took care of everything when we were together. He would Uber me home or take me shopping. It happened really fast. After five dates, when he asked me to be monogamous with him, I just threw it on him. I asked him to give me an allowance. I explained to him that I wanted to be taken care of, but I also didn’t want to have to ask him all the time for money and things, so I would just like one lump sum of money every month for my hair, my nails, or my phone bill. Plus, he was traveling a lot, and he wanted me to travel with him, so I basically had him give me a monthly allowance to cover it. The first month I asked him for $5,000. We ended up being together for a year, and eventually he was giving me around $3,500 a month as an allowance. We wouldn’t talk about it; he would just give me an envelope of money every month on the same day and not mention it.”
Would you have dated him if he said no to the money?
“We were very, very passionate in the beginning, and if he said no, I still would have seen him. Still, my goal was to be a spoiled girlfriend. Once he gave me the allowance, I realized it does get better. The fact that he agreed to it made me like him even more. Like, Wow you really do want to take care of me. And it was easier than any sugar daddy site I’ve been on. Like this is amazing, you know? You can be in a relationship with someone who is going to take care of you in all the ways and still care about you and care about your life and your problems and your goals.
“When I was doing the normal type of sugar dating, I never felt that way. It was always about sex. But the doctor and I had the normal relationship issues with cheating and resentment. I definitely felt that he resented me after a while because of the money. I think he ended up thinking I was using him for the money, and I spent a lot of my relationship trying to prove to him that I just loved him for who he was.”
They’re paying you to be the fantasy so you can’t really fall from that.
“It ended because he was cheating on me, and I found out and broke up with him. He basically wanted me to be his girlfriend and still take care of me, but I had to let him see other people. I told him he was out of his mind. There was no amount of money he could give me. It was such a betrayal to me. We had a really good relationship, you know? It was real — it wasn’t like with my other married sugar daddies who clearly only cared about sex and fun. They didn’t really care about you and your life problems. They just want you to be happy all the time. They’re paying you to be the fantasy so you can’t really fall from that. But the doctor was giving me everything I wanted, both in a relationship and financially, so I was really upset when I found out he was cheating on me. That was my last sugar relationship. Three arrangements and thousands of dates.”
Overall, how much did you make from those arrangements?
“I probably have gotten at least $100,000 within four years. This past year alone, with my ex-boyfriend, I got at least $40,000 or so.”
Tell me about the thousands of dates that you went on — what were those like?
“I’ve been on dates with a lot of men who were not nice, who definitely tried to take advantage of me. I’ve had a lot of negative experiences on Seeking Arrangement. These men were paying me for sex. There was no, ‘Oh he paid me to read books for him and I got $20,000.’ I had a lot of bad experiences of men who were literally just like scammers. You learn that you have to be careful. You can’t trust a stranger — just because he says he’s doing to do something doesn’t mean he will.”
What are some tricks you learned while sugar dating?
“You have to learn the signs of people who are serious and people who are not. If a man requests my private photos before introducing himself I just know that he’s not serious. Men who just want to see what you look like, but when you bring up money they curse you out. The ones who gave me their real name or told me what they do for work, those are the ones where I was like, Yeah he’s serious about this.”
It’s easy to think, Oh I’m young and I’m beautiful, but that doesn’t really matter. That’s not power.
“These men are older, have money, and have power. You think that you’re the one in control, but you have literally no control whatsoever. It’s easy to think, Oh I’m young and I’m beautiful, but that doesn’t really matter. That’s not power. We think it’s power, I know, but it’s not. It’s easy to get really caught up in the lifestyle, but that’s not really your lifestyle you know?”
Did you ever feel not in control?
“Oh yeah, all the time. I didn’t have another source of income that was as much as what they were giving me. So you kind of have to deal with a lot of shit that you don’t want to deal with. That isn’t a real relationship. You have no say, because they know they have this power over you where they can pull the rug out from under your feet, and it’s over.”
Did you feel that way with your ex?
“In a way, I did. In the end when he gave me that offer to stay, I realized, Wow, this is just about control to you. He thought I would stay with him and let him cheat on me just for money. I thought we were in a genuine loving relationship, and it’s just like, no, it’s still about power and control."
So how are you dating now?
“I’ve always been a hopeless romantic so being monogamous is something I want to do. I date regularly now. I still swipe on Tinder but with men who are closer in age to me, and I don’t expect them to fully finance my life. I think for the sake of your mental health, you shouldn’t depend on someone financially and emotionally. You need to be able to do things on your own in order to be happy. So when things end, you’re not losing so much. It’s one thing to lose financially, that’s fine — you can always make money. But the emotional part along with the financial part? It’s too much to bear when it ends.”
Independence is very important to me now.
“Obviously, I still have expectations. I was raised with the idea that the man takes care of everything. I know we are in this era where a woman has to be independent and has to work and has to do this and that, but I do still like to be taken care of by my man. I still want certain things to happen. You can find that in a normal relationship — you know? I don’t know why I had this idea that I had to get a sugar daddy in order to do that.
"I was dating someone recently that I met on Tinder, and it naturally just flowed. On our first date, we went to dinner and the bill came and I didn’t flinch. He paid, and I remember walking home and he said to me, 'Thanks for not making a scene in there about me paying the bill.'”
Would you ever split the bill?
“Maybe. You know, it would depend on occasion. I would split the bill if it’s your birthday, but, like, I prefer for the man to handle the bill. I do. It’s just how I was raised. But I don’t have to do the whole sugar daddy thing anymore. Nor do I want to.”
Has your outlook on dating changed since moving away from sugar dating?
“Independence is very important to me now. In sugar dating, you end up just dealing with too many things. It’s not like I don’t like older men, but they have a lot of baggage. Most of these men have already lived a life you haven’t. They’ve been divorced, they have children, a lot of them are a little bitter.
"I want to date someone who doesn’t have kids, who is also in the same position that I’m in. Not someone who says, Oh yeah, I’ve done that already. I’ve been there already. Yes, I want the guys I date to have to have their shit together, and a lot of guys my age don’t yet and they don’t know what they want, but now I want to have someone I can do stuff with, and it’ll be their first time, too.”
This interview has been edited and condensed for clarity. Have a story you'd like to share? Email us here.