win

Inside The Dark World Of Online Sugar Daddies

I signed up for a site that sets up escorts with men who want to pay them — handsomely — for sex and company. After meeting a slew of men, I learned they often have to hustle harder than the women.

All art by John Gara.

“How different is this from regular dating?” asked one rather bland, but harmless early 40-something guy when we met for a drink. We’d connected through a website that sets up escorts (sugar babies) with men willing to pay them (sugar daddies).

“Apart from the cash upfront and the lack of thinking it may lead to something bigger, such as marriage, I suppose not that different for a lot of people,” I replied.

“Exactly,” he said.

I wasn’t actually interested in taking his money for sexual favors. Rather, he was among around 10 men I met in an experiment I undertook over a period of a few weeks to see what it was like to meet men through one of these escort set-up sites as a prospective… employee.

These kinds of arrangements aren’t that unusual in New York, where I live. Having interviewed an escort and married man who hires escorts, I was curious about signing up for one of the websites that hooks them up with each other. What did people derive from the transaction, beyond quick sex and quick cash? Maybe it was shockingly normal — alluring beyond the obvious reasons.

I also wanted to find out why these kinds of relationships persist. Sure, they’ve always existed somewhere. But it seemed to me that the proliferation of post-collegiate debt, an atrophied job market, and rising unemployment for single ladies — not to mention the speed and anonymity of the internet — might make these arrangements more attractive to young women with rent to pay and dreams of living The Life in New York while they were still young. Besides, dating in New York sucks anyway.

But what I found is that the men often have to sell themselves just as hard — perhaps harder — than the women.

Let the seduction begin.

I set up my account for free and got to work on my profile. (The site is free for “sugar babies” but not for the “sugar daddies,” who can pay up to $2,400 a year for use of the site as members whose income has been verified.) Being 30, I wondered if I should be honest about my age seeing as most women on there (even if their photos were clearly screaming “born in the ’70s”) claimed to be 25. Student sugar babies can get their accounts “certified” by using their .edu email addresses. I ended up keeping the physical description honest, but shaving five years off my age to attract the kind of guys who populate the site (physically, I can pass for five years younger). I uploaded a photo, as blurry as possible, and the site approved my account. The rules clearly state that use of nudity and celebrity photos are prohibited, though a lot of the photos on there look one step away from a Hustler pictorial.

The site also asks you to state how much you want per month: $1,000 or so up to $20,000 or more a month. But $20,000 a month?! That seemed extreme. I decided to go for $5,000-$10,000 a month. I noticed a lot of the women out in the Midwest want $1,000, but the asking price increases in urban centers like Los Angeles, Miami and New York. I figured a higher ask would give an impression that I was “worth it” for some of the certified Premium Sugar Daddies, the kinds of guys I was hoping to meet.

Shortly after my profile’s approval, emails started flooding my new fake account. One was from “International Finance Don Juan.” He wrote: “You look hot. Let’s meet.” He claimed he was exotic and athletic, over six feet and an independent stockbroker on his profile. After some small talk, he asked to meet me at the W — a “cool” luxury chain where seemingly all these guys wanted to meet or get a hotel room. “Don Juan” had sent a face shot of himself. It was cropped and a little blurry, but I had a general idea of what he looked like. When he walked in to the lobby bar, though, instead of “athletic,” he looked as if he could have checked off “more to love.” I guess all that matters is that these guys have the cash they say they have.

At barely 5’7” and almost totally bald minus small wiry patches of hair, he was sweating through his short-sleeved collared shirt. I tried to shake his hand, and he tried to hug me, which put my face almost directly into his armpit.

He asked what I’d like to drink. I said I liked pinot noir or champagne. “Oh, Prosecco is basically the same thing,” he said, and ordered me one. I had made up a story that I was a graduate student in literature at Sarah Lawrence so I was only in the city once or twice a week to see friends. He wasn’t trying to feign interest, but was looking my body over in a conspicuous way.

“You’ve got an amazing ass,” he said. “I looked when we were walking in. I hope you don’t mind.”

He attempted to wink, but it seemed more like a tic. I said thanks in the most convincing way I could to a sweaty, slobbering guy with the most repugnant perpetual hard-on visible through his khakis. “You like me?” he asked.

“You seem very nice. I’m just, I’m just suddenly not feeling well,” I blurted out.

“You feel sick, or you’re not into me?” he asked. “You know, if you want, I live close. You could come and lie down and I can give you a massage. Since it’s our first time meeting, once you’re better, you could just give me a blow job. How about $550? Probably the quickest $550 you’ll ever make, huh?”

He tried that winking again and it failed in a spectacular fashion. I was surprised by the lack of verbal foreplay and how quickly he got down to business.

“I don’t think so,” I said. “Look, I am sorry. It’s just that I’ve never done this before and I’m not sure this is for me. A friend had recommended it to me and I’m not cut out for it.”

“I think you’re cut out for it,” he said, coaxing me. “You’ll do just fine. I will make you feel so comfortable. I’m not looking for a long-term thing. Let’s have some fun. Life’s short.”

“Yeah, I — it’s just that I have to go,” I said. “I feel sick.”

“Oh sweetie,” he said. “I’m sorry. Let’s meet later then. Or tomorrow. I really like you.”

“But you don’t know me,” I said.

“I like how your eyes are,” he said. “Honest and real. Big.”

“I really have to go,” I said, picking up my bag, wondering how many girls this guy must have met and used that line on. I climbed down from the stool, catching my dress on the back of the chair and almost tripping. I felt like I’d be found out any second with this guy, who was still sweating and breathing heavily through his mouth in between smiling at me, trying to make me feel comfortable while the hairs on the back of my neck stood up every time he touched my arm. Something about this man set off my fight-or-flight instinct. The way he sucked on his teeth and bit down every few minutes made me feel like I could easily end up being drugged and assaulted in his bed if I’d ever taken the bait.

“I’m so sorry, look it’s not you,” I said. I have no idea why I felt like I needed to explain myself to him, but he was sitting in front of me, now looking some version of disappointed.

“You’re missing out, then,” he said. “I can find a new girl any time I want. I’ll find one on my phone now. I’m not wasting my time here. You wasted mine.”

His disappointment was turning into anger. I kept apologizing, but said I was leaving one more time and he just said, “Fine. Suit yourself.”

I had heard from women who had been on these sites that you’ve got to do the email dance beforehand for a little while. Now I understood why. But I decided that I couldn’t just stop the experiment with that kind of experience when I’d heard enough stories of pretty normal — or at least entertaining — exchanges between sugar babies and sugar daddies.

After my Don Juan experience, I decided to meet “Tommy.” He lived in New York (a lot of the guys seem to live elsewhere, but want romps while in Manhattan) and said he owned some kind of design company. Like most of these men, he was vague. We met at a bistro not far from my office. I was getting bolder, less paranoid, about these meetings. I figured, perhaps naively, that we both had an equal amount to lose.

“Alex?” a man said.

I turned to see a slightly pudgy but cute, hipster-looking guy, wearing tortoise shell Ray Ban glasses and what looked like head-to-toe John Varvatos.

“Tommy?”

“In the flesh, my lady,” he said.

He had that kind of fast-talking, well-educated, sardonic New York cadence people seem to adopt after years here.

“How did you know…”

“You’re one of the only women here, and you are the only person here not dressed like a banker,” he said. “Voila. Pretty obvious.”

We sat down at a table by the bar and he edged up on his chair, getting right down to business.

“So, like I said in my emails, I want something different.”

“Okay…” I said.

“Don’t get me wrong, you’re attractive enough, don’t get all ego-bruised, but I could tell from your emails that you’re smart. I like smart in real life, I love smart. I just don’t like smart when I’m meeting these girls.”

“Okay?”

“I don’t want to fuck you,” he whispered, looking around. “Let me explain. Give me a minute. I had this Colombian girl, so hot, studied dance and we met online, blah blah. We had a thing for over a year. It started off with us sleeping together, then I’d give her some money or go shopping. But look, I’m already married. I get bored. I got bored. She was a little bisexual, so I asked her if we could start getting girls to come into our sessions. Then she got kind of bored with it and suggested that she just find me girls. I loved it. It was awesome. I’d give her cash and she’d find me these hot little dancer girls. But then she had to go back to Colombia. That sucked. I’ve been looking for months for someone who could do what she did. But it’s impossible. Plus all these girls are basically escorts on there.”

“Okay…” I trailed off.

“You look confused. I want to pay you $200 to scope out girls, and $500 if I end up sleeping with them. All you have to do is get me their numbers, emails, and find out if they’re my type. Here…” He pulled out his phone and showed me a picture of what looked like an 18-year-old girl in a hoodie. She could have been any college freshman at any liberal arts college in the U.S. “I love this,” he said. “I really love this. Nothing kinky. Just young. And skinny. I like basically no curves. I want you to be my very good friend, who makes me very happy. I can make you happier without having to deal with these skeevy guys out there. I’ve heard horror stories from some of the girls I’ve met.”

“Like what?”

“I don’t know, just really old dudes who pretend to be 40 and turn out to be 60,” he said. “Dudes who want you to dress up like school girls, that cliché shit. Just absolute fucking weirdos who want to cuddle for $1,000 a night while you wear a little nightgown. Then one girl told me some guy who was obsessed with feet and wanted her to get him off with her foot. That he was a banker or something and said that he wanted her to walk on his back and then turn him over and rub him until he…”

I grimaced. He laughed. “You look so disgusted! Too funny. Come on, like you haven’t had some dude ask for weird shit? I’m guaranteed the most normal guy you’ve met.”

He kept looking at his watch. We ordered sparkling water and salads but I had a feeling he was looking to bolt before any food was served. “What do you think?”

“I have to think about it. It’s not what I was looking for, really, but I understand why it would be easier.”

“Yeah! You don’t have to sleep with old dudes! Come on, this is so much better,” he said. “They probably fantasize about you being their daughter’s friend or something. So gross.” He was more judgmental about this than I could ever have imagined.

“But you’re looking for barely legal disposable sex partners,” I countered.

“Yeah, but I’m only 38, and not gross,” he said. “I am very vanilla. You can tell the girls that. Tell them I’m 33 too.”

“I didn’t say yes,” I said.

“Okay, well if you do, tell them that. Oh and I love American Apparel. All those leotards and little shorts. I’ll take them on shopping sprees there. Let them know. I have to go. Email me, tell me what you think,” he said.

“I will, but I don’t think I can do this,” I said, considering the grim reality of being the personal madam of this youngish, apparently successful, snarky guy.

“I want you to be my very close friend,” he said. “Remember, $200 upfront then $500 after. It could thousands a month if you can scope the right ones out… I know it sounds bad. I have to go. Bye, babe.”

With that, he kissed me on the top of the head and gave me money to cover the lunch and I sat dumbfounded by the 15-minute exchange. Still, the appeal of these arrangements was not lost on me. I have considerable student debt from attending two expensive private colleges. I get why having someone wealthy helping to pay those bills is attractive to a lot of women. At moments during this experiment, I started thinking that going for one of these guys wouldn’t be such a huge stretch. I began to understand how morals can start loosening and people can start rationalizing a quid-pro-quo relationship.

I didn’t take Tommy up on the offer, but I still get a lot of emails and instant messages from him on my fake email address. “Babe, where are you? Can you please reply? I haven’t found anyone. Can you let me know if you can meet?” I had told him I was too busy and it wouldn’t work, but it took him a while to relent. I guess it is harder to find just-about-legal girls in this town than it seems.

After Tommy, I decided I was going to meet Paul, who appeared to be articulate and sweet in a Northern California kind of way. (He said he was vegan, runs a computer company and went to UC Berkeley. In the photo he sent me, he was on a mountain wearing a pair of Tevas and a backpack.)

He told me he doesn’t live in New York, but comes often. When finally met, he was shorter than I expected, but quite handsome actually, and exactly how he seemed in writing. He pulled out my chair for me at the organic restaurant he had selected, made sure I enjoyed my spinach salad and asked if the almond-crusted salmon I ordered was cooked to perfection. He didn’t mention anything having to do with the site or an arrangement until a few glasses of wine had gone down.

I was tempted. Here was a guy who was actually trying to get me to like him. He wanted to win my approval — and then give me thousands of dollars to, I guess, worship me. The lines started getting blurry with him. My debt and financial worries started creeping into my mind as I looked at this gentle, geeky man who obviously lacked self-esteem around women. You feel quite powerful when these men are trying to pitch themselves to you in spite of the scrutiny you know you’re undergoing, whether tacit or explicit.

I asked him if he’d done this before; he said he’d seen two girls in New York. The first one lasted for about a year, and he’d deposit $4,000 in her account monthly no matter how often he came to the city. Sometimes it would be once a week, other times only once a month. They broke it off when she started dating a guy seriously and he saw an email from Paul and freaked out.

“She said that she was in a lot of pain about breaking it off, but she had to do it,” he said. “I wonder though if it was the money she missed more because she kept bringing up meeting secretly once a month for $4,000 a few months after she broke up with me.”

(He seems to think they had a real relationship. Maybe they did.)

“It made me feel disgusting, honestly, and I started getting cynical,” he said, swigging his wine now at a quicker rate. “Anyone ever tell you you have a sort of sultry Veronica Lake thing going on? You know who that is, right?”

“Yes,” I said. “Thank you.” He then went full throttle into how he met a girl who was in college somewhere close to New York, but not in New York and they “had chemistry” and started seeing each other. He wanted it to be the same deal as before: Meet when he could and he would put in $4,000 like clockwork on the first of every month. She took the first $4,000 and met him once more after the first time they slept together.

“It wasn’t that great, not like the first one,” he said. “I felt like she kept looking at the clock and I wanted her to stay the night and she always said she had to get back home and would ask for another $200 to get home.”

She kept in touch with him on email and was supposed to meet him in New York in the middle of the week — they’d agreed she would stay over. She arrived at his hotel room, slept with him and said she didn’t feel like going out to dinner. She said that she wasn’t feeling well and he let her go, saying that he had a feeling she was lying and just wanted her envelope. He did give her the $4,000 for what would have been their second month. After that, the girl was basically MIA. Other men had told me about this pattern — the mysterious disappearance of girls after they get their cash.

“She would reply to emails, but then not commit to meeting,” he said. He finally gave up and said that he was about to give up entirely on finding someone new. “I felt used and dirty,” he said. “Yes, I get the humor here. The girls are maybe supposed to feel that way but men are more fragile than women ever think.” Then he had a slew of bad experiences, much like a lot of the men who line up sugar babies: escorts who pretended to be “normal girls,” but who were just looking for a quick $2,000 an hour; women who lied about their [fill in the blank]: age/weight/height/education level/intentions.

With Paul and all the men I met, I detected an underlying reservoir of great expectations and ensuing disappointment. It was as if they all harbored a secret hope of finding a little “Gigi,” as in the French movie about a wealthy playboy and a courtesan-on-training-wheels making a passionate love match. Even the ones who tried to be super-sexual and forward seemed like they needed reassurance and someone to tell them they were worth time and effort. I found that more often than not, most were married though some were divorced or life-long bachelors. Sure, there were some raging narcissists, like the 65-year-old former lawyer for a royal family who told me I’d never have a “fuck” like him in my life, and others who were just looking for an escort for an hour in a hotel room ending with an envelope and a “have a nice life.”

In the end, I told Paul on the phone that I wasn’t ready for an arrangement, but would like to be friends. I did mean it on one level, but knew of course I wouldn’t really be friends with him. There had been too much deceit on my part. He told me that if the money wasn’t enough, he could increase it by $1,000. I said it wasn’t that. I found through all the men I met — this is just a sample — the money seemed the least of the issues at hand. There was always some long talk about how they wanted the girl to “really want” them, of how chemistry was so important, of how little time we have and how difficult it is to find someone compatible.

Really, a lot of these men were looking for love — or some perverted, alternate form of it — in the entirely wrong place. There are probably more International Don Juans for every earnest Paul, but a lot of the guys seemed somewhere in between — well-educated, rich or rich enough, bored in their marriages, with little pockets of extra time to spend finding a side dish who would come when they wanted and leave when they decide they’ve had their fill.

The single guys I met made it clear they weren’t looking for any type of real relationship. They liked the idea that the money bought them the ability not to commit. One guy I met said that his job was his girlfriend, that sometimes he thought of money as his love of his life. He even went as far as to say that the money can’t keep him warm at night, but it won’t leave him and won’t end up making him try to change. The funny thing with these men is that there was a freedom they felt with me once they thought of me as a commodity, of someone who had put herself out there on the market to be bought in increments. If I had gone for a drink with a banker on a date, he — of course — would never say any of that out loud.

Even if I’m well-educated, probably someone their parents would think of as a “nice girl,” men seeking escorts place me in an entirely different category. That category was “disposable,” and “transient,” and “just for fun.” The men I met during this experiment are masters of compartmentalization. The one box they just never wanted to touch was emotional commitment. It’s amazing how much the money allowed them to keep that at bay.

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