I Thought Being a Sugar Baby Was Going to Be Easy Money, but My First Paid Date Taught Me Otherwise

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“It’s not like you sleep with them,” I remember my friend Jess* nonchalantly explaining to me about the duties of a sugar baby. We were around 17, and at this moment in time, Jess had never actually had a sugar daddy, but she knew about corners of the internet I had yet to discover.

Jess found out about Seeking Arrangements—then an online dating platform designed to connect young women with wealthy older men—on Reddit, where she stumbled upon a thread about the experiences of sugar babies. She told me tales of girls who got paid just for texting. Others, she said, would go on dates or put on a girlfriend act but never actually sleep with the men. There were other girls who never even had to meet men IRL—they were simply paid for having digital relationships with men who were on the other side of the world. The way Jess explained being a sugar baby was that it was sex work without the sex, something equivalent to being an escort with entrepreneurial spirit.

I was intrigued. I had less than a year of minimum-wage savings to my name, and a lavish New York City dream that felt entirely unattainable. It sounded simple enough: I could rely on my desirability and make a living off of it. Talk to an old man, make him feel wanted, easy money, I remember thinking to myself. Before I had even turned 18, I was setting up my Seeking Arrangements profile under the moniker Sarah Rose just to see what was out there. Very aware that I was a minor, I had no intention at the time of dabbling any further than an initial exploration, so I just clicked through an assortment of profiles, from men whose listed net worth was $150,000 to those who seemed much wealthier than that.

Sugaring was a normal, valid side hustle for a collegiate, fresh New Yorker with pretty privilege like myself.
_{—Ella Snyder}

A year later when I finally came to New York City for college with scholarships, student loans, and the generous help of my family, I met real sugar babies. These women were no longer characters in a friend’s story; they were my classmates, coworkers at my retail job, and models at the promoter’s table in the nightclub. I met girls in my freshman class who giddily shared that their designer handbag had been gifted to them while on a paid date with a man they’d never see again.

The world of sugar babies was so popular in my little bubble that it garnered the attention of our college newspaper. It was official then: Sugaring was a normal, valid side hustle for a collegiate, fresh New Yorker with pretty privilege like myself. But as I listened to more and more stories from my peers, the veil between how we all talked about sugaring and what sugaring actually was began to get pulled back. It was more than pearly grins, complacent nods, and surprise Louboutin heels—it really was sex work.

I’d come to learn this through a friend, Maeve,* who regularly cam-girled from her bathroom or room, video-chatting with men and putting on a show for cash tips. To recap: My lavish New York dream was still very not lavish. I’d been actively draining my savings and, as a result, my curiosity about my classmate’s work-from-home method of income increased. I asked her about it to the point of basically requesting a how-to, which she gleefully gave me.

I never built up the courage to try camming myself though. I was too paranoid about my digital footprint, the permanence of the internet, and my safety as a stealth trans woman. With that boundary firmly established, my thoughts around Seeking Arrangements changed when I saw Maeve early in the evening one day, arms weighed down with bags of groceries and fists clenching a thick stack of 20s. “I went on a date with a sugar daddy!” she said. Her disposition seemed cheerful, and her financial woes were a problem of the past.

I was young, impressionable, and wanted an allowance that would let me keep up with the girls carrying Birkins as their backpacks.
_{—Ella Snyder}

She told me she made $500 for 30 minutes of “work,” which she shared meant giving a blowjob, only after I probed a bit. Maeve informed me that this was a lot more money for a lot less work than camming. She seemed willing to try it again, and I started thinking I might be able to do it too, but my version would be different.

Looking back on it now as an adult, I recognize that the part of myself willing to try being a sugar baby still believed the tales I’d heard from my high school friend Jess: that my experience wouldn’t be like Maeve’s, that sex work without sex existed, and that I could be an outlier from what I was, at that point, recognizing was the majority. I was young, impressionable, and still wanted an allowance that would let me keep up with the other girls carrying Birkins as their backpacks.

That night, I logged into the Sarah Rose profile for the first time in over a year—now fully 18—and began swiping like it was Hinge. I scrolled through profiles of obvious dye jobs and salt-and-peppered men, unsure of what I was even looking for.

I landed on the profile of a guy named Tim,* who lived in Colorado. He was 60-something and older than my dad but looked active and outdoorsy. His profile said he only traveled to New York occasionally, which I liked. It felt comforting and secure (as much as it could when meeting a stranger thrice my age off the internet), like if things quickly went south, I wouldn’t have to worry about ever bumping into him, like Rachel Senott’s character in Shiva Baby. His smile leaned more friendly than serial killer, so I decided to take a chance. I sent him a Like and said “Hey :).”

He responded with, “Hi! Coming to NY next week for work. Any interest in grabbing a coffee? Would love to meet. Can pay $250.” Feeling courageous, I agreed to this coffee date. Besides, it was just coffee, right? He wasn’t going to want to afford me the lifestyle I dreamed of without ever meeting me, I figured. We decided to meet at the Ace Hotel midweek, midday. I made sure to tell two friends of my plan who would ensure I was not kidnapped and/or murdered.

I was here to make $250 drinking coffee with a man whose thing was paying for young women’s company.
_{—Ella Snyder}

I arrived in the hotel lobby earlier than our scheduled time, and I could feel the architecture of the building swallowing me whole. For the first time in this process, I really felt so small and so young. Business professionals sat in velvety armchairs, typing on their laptops, making deals on their phones, and there I stood, with my miniskirt and school bag, feeling oh-so Lolita. The last time I had been in this hotel was for a friend’s Sweet 16, and now I was here to make $250 drinking coffee with a man whose thing was paying for young women’s company.

Before long, Tim strolled into the hotel’s coffee bar and greeted me with a kind hug. We ordered our lattes and grabbed a seat on a bench in a quiet hallway. We exchanged niceties between pauses of awkward silence. Our conversation felt forced, but I knew that he was supposed to feel like I cared, so I kept asking questions, smiling, and agreeing. I didn’t feel gross or guilty doing this—I felt like I was acting, improvising through a performance with a new costar who had no clue that we were doing a play.

Before long, he said, “I have another $800 for you if you’d like to come up to my room.” There it was. A true proposition that made it all more real. I was no longer a unicorn, being paid solely for the presence of my youth and beauty, nor had I found the one guy who’d buy me designer boots without any expectation of something in return. I was just another college freshman sitting with a cup of coffee, being solicited for prostitution.

Having set no prior expectations or boundaries for our meeting, Tim’s proposition wasn’t a complete shock, but it was a wake-up call to the treacherous waters I’d been wading into. “That’s not really my thing,” I told Tim, and he politely respected my choice.

My rejection felt like the perfect natural end to our time together, so I made up an excuse about a class I should be early to. He pulled out his wallet and handed me five 50s. Born a people pleaser, I tried not to feel too guilty accepting this cash and holding on to my boundary.

I’m self-aware enough to know that a long-term setup like that would be unproductive for me.
_{—Ella Snyder}

After Tim, I couldn’t bring myself to open Seeking Arrangements again. I didn’t enjoy pretending to like him or our conversation, and the tightrope between dating for money and having sex for money in reality was too thin. I didn’t want to revisit the mental negotiation of agreeing to meet men who were actively seeking this huge power imbalance (in secrecy, no less) and then have to reject those same men. After all of this, I realized the life hack everyone was always talking about—sex work without the sex—was actually just...work. I don’t knock anyone who gets their income this way. But I knew if the work was going to feel like work (instead of a movie montage of me plucking designer bags from retailers like they were growing on trees), I was more cut out for a job that had me clock in and taxed my earnings.

I’m self-aware enough to know that a long-term sugar baby setup would be unproductive for me. I can’t live my life like it’s a play when I am actively trying to ground myself in reality. Ultimately, I know I want to date for love and marriage. But here’s to hoping for the occasional no-strings-attached shopping spree on someone else’s dime along the way.