World Wide Crazy News!

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.

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