Editor’s Note: All names have been changed out of respect to individual parties. This article contains explicit language. Seeking Arrangement is, more than a dating service, an endurance test. That’s how I felt when Ethan’s message landed in my inbox, three weeks into my gradual descent into dating hell. I’d had enough of these older men’s sob stories, their sense of self-entitlement, their patronizing way of telling me that I was smart for my age. Yet Ethan’s message was cute and succinct: he told me that I was pretty and that he would like to get to know me better. No ex-wives, no page-long love letters. His profile painted him as a witty, multi-talented young guy who had sold a company at a young age, allowing him to spend most of the year traveling and learning languages.

This already looked promising – and then I saw his photos. And his bank balance, a feature of every sugar daddy profile. He was young, loaded and very handsome. There were traces of messy hair, motorbikes and leather – very much my type – but the way they were put together was more Hedi Slimane than Sid Vicious. I felt like I was looking at a pastiche of every guy I’d liked in the past two years packaged into an older, sleeker model. And, while I’m rarely impressed by wealth for wealth’s sake, I did a double-take when I saw the figure listed as his verified income. He was worth more than my entire inbox of sugar daddies combined.

Ethan was a unicorn in a compost heap. I waited a day to reply, and briefly mentioned my love of Southeast Asia and cinema, subtly testing to see where he would take the conversation. He replied almost immediately with stories of favorite places in Luang Prabang and asked me if I had seen the latest Errol Morris documentary. Truly, a unicorn.

We talked for another few days, and finally decided to meet for drinks on Tuesday night. Instead of the usual leather pants or ripped jeans, I dressed tamely for the occasion: a navy cashmere sweater, tapered burgundy pants, a long, burgundy coat, plum lipstick, light eyeliner and my hair in a loose ponytail.

An hour before we were supposed to meet, Ethan texted me to meet him at Republic on Union Square. I took a while to find the bar, walking twice around the Square before noticing the small entrance. As I reached the door, I realized the bar was closed and the street was virtually empty. He’d stood me up. I was about to text him and give him a piece of my mind when he rushed over to me from around the corner, his Burberry trench flying behind him.

“Sorry, sorry! I was parking my car!”

My first reaction was to blurt out, “Fuck, you drive?” I had never met anyone who drove in the city. He must be an idiot or have a car worth showing off, or both. We quickly hugged, and I pointed to the closed bar. He pursed his lips for a moment and, slowly pausing, asked me if I liked tea.

I nodded. He took me by the hand and led me around the corner to his Ferrari. I jumped in the passenger seat as he closed the door behind me, at which point I realized I was in a stranger’s car driving uptown — if you’re reading this: hi mom, I’m fine. The sensation of speeding up Broadway on street level was such a new feeling that I spent the first few minutes staring out the window, beaming. He looked over and smiled.

“So I know this little tea place near my apartment,” he began, going through a range of loose-leaf sencha blends I might like. I think he could tell how bemused I was by the offer – this wasn’t standard SA fare by any means – and asked me if I’d rather go to a bar. He pulled over by the sidewalk and looked at me, concerned. “What would you prefer? Honestly, I just feel like talking. I don’t wanna get you drunk or anything.”

I said we should go to the tea place then. We pulled up outside the storefront on 34th and grabbed a table by the window. It had been almost embarrassing to hear Ethan, a seemingly intelligent, attractive young man, attempt to convince me that he wasn’t a pervert. For the first time, it struck me how demeaning SA was for both men and women, albeit in different ways. Just as I had met a good number of NYU girls through forums who were using SA as a means to an end — to get through college, start a career — there was no reason to think that every sugar daddy was monstrous. After all, this was an expensive and time-consuming commitment — $1,200 a month for a diamond club certification. There are far more convenient ways of being creepy and misogynist, if that’s what you’re into, without going through the rigmarole of planning a date and pretending to be interested in what a girl has to say.

Ethan seemed more interested to know about me than the other men had been. He kept asking me questions and every time I spoke his smile would widen a little more. I knew how to make him laugh, how to make him open up. Soon, we were discussing our childhoods — his in California, mine in Dublin — our parents and our recent dating histories over jasmine green tea served in small cups. He had started out with a hedge fund after college, amassed a quick fortune, launched a tech company with his savings and sold it at 32. That was two years ago.

These days, he spent most of his time between Europe and New York, learning French, Spanish and supercar racing. I name-checked several club nights in Paris to make sure he wasn’t bullshitting. Not only was he intimate with the French electro scene, but he was also good friends with two of my favorite DJs and they stayed at his place whenever they were in New York. I again double-checked him with a couple of obscure references to their back-catalogue and tour schedule until I had no doubt that he was telling the truth.

He seemed well-adjusted but bored. I asked him if he was happy, and he seemed a little taken aback. I rephrased: what are you doing here? He looked at me properly for a few seconds. I think he understood what I meant.

Out of courtesy to someone who was honest, I’ll brush over the details. It wasn’t a pretty story. It seemed his own fortune had closed him off from the world. He showed me photos of his former fiancée, who had called off their marriage years ago because she felt that he was never there. He had tried meeting women in similar high-level positions, but the successful ones were always too busy for relationships. He described in terrible detail his time with sex-workers, the way he used to treat them and the feelings of self-loathing.

I wasn’t sure what to say. While I certainly didn’t feel sorry for him — he was living the life, by any standard — it was clear that he had issues of his own. He asked me if I wanted to join him in Paris next weekend, and I told him I’d think about it. All I had to do was call, and we could visit his house in the Hamptons.

We were so clearly compatible, and yet something inside me felt deeply uncomfortable about how invested he was in making me his dream girl. I already felt for Ethan, but what was I going to bring to the table? Youth? Optimism? The openly transactional nature of SA had really got me thinking about the things that we bring into relationships. As appealing as I found the idea of going to Paris with him, I couldn’t pretend to be his arm candy — even if he didn’t see me this way, I would myself. A sugar baby is never sad, is never underdressed, is never anything less than a dream girl.

The problem with SA is that the real guys, the good guys, are genuinely looking for smart, pretty and well-traveled girls to spoil and take on business trips. They don’t want another escort or model; they could land one of those at the drop of a hat. Ethan wanted a real girl who liked him for more than his money and who had time to get to know him deeply. But why would a girl like that be on SA in the first place if she wasn’t deeply struggling?

Did we have an obligation to be real with each other? Ethan liked me precisely because we had shared similar experiences and mingled in fairly similar circles, and because I made no mention of compensation. That’s what made me real, but also what made my presence totally implausible on a site like SA. Did I owe this man anything? No, nothing was written in stone - but for some reason, I felt like I had connected with him, and if we were going to be honest with each other, it would be absurd for us to perpetuate this fantasy.

Ethan drove me home and stopped outside my apartment on 23rd street. Kissing me goodnight, he seemed happy. “I’ll see you next week, yes?” I smiled, unsure what to say. He texted me the next day. And the next. He invited to me drinks with his friends, then to a benefit he was organizing. I never replied. Eventually he stopped. SA was over, and I went back to hanging out with guys my age.

I still think about what might have happened if I had replied to Ethan’s follow-up texts. Maybe we would have gone to Paris together. I might even have been able to shake my feelings of youth and inexperience in the face of his 34 packed years. No compliments and gifts could ever make me feel vaguely satisfied about being dependent on a more successful man, even if I tried. It made me feel profoundly uncomfortable, and I’m glad I realized this at 19 instead of several years into marriage. That would be rough. In the end, the experience helped me to figure out what I was worth, on my own terms.