Graphic by Andrija Klaric/TheGazelle

The evening of our date, I ate a quiet dinner back home and left for Brooklyn around 9 p.m. I was standing outside the bar of my choosing, freezing and smoking a cigarette as I waited for Doctor Sugar, when it hit me how absurd and potentially dangerous this entire situation was. Although I had read a few girls’ testimonies of the typical Seeking Arrangement date, which involved the standard dinner or drinks and hashing out the details of a potential arrangement, there was also a good share of horror stories circulating online. That said, I figured that staying in a public place and going easy on the alcohol should stand me in good stead, regardless of whatever kind of guy this was.

My stomach dropped a little as I ran through lines in my head, reminding me of nervous high school theatre auditions. I spotted a man in his early thirties walking down the street towards me. He looked more or less like the guy in the picture, although a little older and shorter than expected. He wore a leather jacket and a nicely draped scarf, and greeted me confidently with a small squeeze of the shoulder. “Isabelle, right?” he asked, as if fishing through a backlog of young brunettes.

I smirked and said hi, surprised by how confident I sounded in my attempts to match him. I wondered how long I could pull off the veteran sugar baby act. We grabbed a table in the corner and I scanned the menu, excited to finally be able to afford coming to this bar. While I had been cautious of the fact that some people might give us strange looks given our visible difference in age and walk of life, nobody batted an eyelid — which, looking back, probably says more about New York than it did about us.

After some initial joking around about various weirdos we had spotted on the SA website, we got into more personal matters: he told me about his college years at Yale, his current research position at Langone and his recent-ish breakup with a long-term girlfriend. Between the long work hours and his friend group taking sides with his ex, it had become harder and harder to meet women in his thirties, which was why he had turned to SA. He told me that he had been on a few dates already and was playing the field to see what was out there. I replied that I was doing the same.

The openness between us was refreshing. Perhaps because I wasn’t looking for romantic attachment, I found it much easier to discuss with him the blessings — and curses — of dating in New York: the endless supply of interesting people, making it terribly difficult not to fall in love on a daily basis; the gradual loss of interest in those same people as you realize how easily they come and go; the feeling that you always could, and should, find someone apparently better; the solitude of big city life; and the defensive “don’t fuck with me” attitude that keeps people from getting close enough to realize how much they might actually long for closeness.

A second round of drinks and his grilled cheese arrived, lightening the mood in a way only grilled cheese can. I told him that I was a film student based in New York for the time being, and that aside from meeting older men, I was hoping for someone to show me around some otherwise — possibly, financially — inaccessible parts of the city. He seemed surprised that I wasn’t asking for a fixed sum, and asked me how much I paid monthly in rent. “Oh, not much…” I replied, stalling. If I told him that it was fully covered by my scholarship, he might guess that I wasn’t really in this for money — and if so, what? An article? Never. I bluffed a figure between the $1200-$1400s per month, and he seemed to buy it.

He offered to pay my rent in exchange for meeting once a week. If we vibed, our commitment, along with my financial gains, would increase exponentially. Slightly tipsy, I laughed out loud, unsure as to whether this made me feel more like a CEO or a sex worker. He seemed to mistake my amusement for flirtation and leaned in for a kiss, which made me laugh even harder. I told him I had to go home as I had class the next day, and he suggested we check out his new loft on Wythe Avenue. When I assured him that I really needed to return to my dorm, he pulled out his iPhone to show me photos of his recently decorated living room, with an air of, “This could be yours one day!” I shuddered and said goodbye, giving him an awkward hug and walking briskly to the Bedford Street L train.

The next two men were unremarkable: between the fashion photographer from Greenwich Village — creepy — and the plastic surgeon from Miami — very creepy — I couldn’t help but feel that I would need to be truly desperate for money to every involve myself with this bizarre species of rich, overworked male.

Ironically though, I actually felt safer going on dates with these strangers than if it had been any random college guy; operating under the SA umbrella, if one of these men overstepped my boundaries in any way, I would have reason to report him to the website administration and to one of the many influential sugar baby blogs. One day, after receiving a particularly unsavory string of messages, I was surprised by how quickly SA administration replied with news that they had received a number of recent complaints about this member. Within twenty-four hours, his profile had been erased. No more sugar for you, sir.

In the midst of all the Title IX debates shaking college campuses around the USA, I was pleasantly surprised to find an environment in SA in which naming and shaming dangerous men was not just encouraged, but crucial to the business model of the website. If sugar babies felt unsafe, the entire system would collapse.

Anthropological curiosity aside, I slowly began to feel resigned to the fact that I would never find anyone vaguely likeable on SA. Then Ethan came into the picture.

The author is a contributing writer. Email her at feedback@gzl.me