A few weeks into a relationship, Evan Jacobs was obsessed. Not with his new girlfriend—with his plan to pay for sex in Amsterdam.

I met my ex-girlfriend by replying unironically to an ironic Craigslist ad seeking a man who had scored highly on the SATs. She told me I’d intrigued her. Half Czech and half Colombian, she had cute, squinty eyes and hair like liquorice. Her body was soft and curvy; her wit was sharp. On our first date, we ended up at a bar that seemed to attract only polo-wearing ex-frat boys. About 90 minutes into it, she asked, “So are we going to make out, or what?”

By our fourth date, we were dipping our toes in the ocean of couplehood. There was only one problem: I had made a decision weeks earlier that had me excited, even obsessed. I was days away from a two-week trip to Amsterdam, and I was going to get a hooker.

♦♦♦

Being an overachieving Jewish social outcast had warped my sense of self-worth and my definition of a healthy sexual relationship. My love life did have its successes, but more often, it had spectacular failures: girls who had never showed for dates, denied me their numbers (or even names), or pulled their heads away when I went in for a kiss.

But now I was in New York, the land of the single-and-looking. I was set on reversing course. I was determined to outshine those charming and attractive guys from my young adulthood who never had my problems.

To this day, I have never been to a strip club (even a Hooters). Being so close to raw objectification makes me uneasy. But Amsterdam had something New York didn’t: a completely legal and regulated sex industry whose workers are healthy and don’t answer to pimps. If anyone was going to be objectified, I thought, it was going to be me.

I was young. There was a whole world of experiences out there—some innocent, some vile—and I wanted it all. The seedier elements of society had always fascinated me. And because I was paying for the sex, I could take the opportunity to try things that I had been too embarrassed to propose to anyone else. How could I not do it? I convinced myself I would regret it if I didn’t.

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I had never cheated on a girlfriend and didn’t plan to start, but the girl I was dating was not technically a girlfriend yet. We hadn’t discussed being exclusive, although I was, and I suspected she was, too. Still, I didn’t feel right withholding my agenda from her.

One night before I left, I told her my plan. She reacted with calm kindness, telling me she completely understood, and had she been going, she would probably get one as well. Yeah, right, I thought. But I convinced myself to take her word for it.

♦♦♦

On the first day in Amsterdam, my friends and I walked through the red-light district. Each street was tiny, coated in dust, and lined with glass doors. Women stood behind the doors, watching, beckoning, sometimes standing with their hands on their hips, sometimes dancing.

Some doors had the shades drawn, signifying occupancy—or maybe a lunch break. There were groups of giggling frat brothers at some windows, businessmen at others. Occasionally, I’d see a middle-aged man walking alone, smoking a cigarette, making eye contact with nobody.

It was at this point, this first encounter with the red-light district, when I realized I was actually going to go through with my plan. Part of me had hoped—expected—that I would back out at the last second. I had changed my mind several times on the airplane. But when I saw the prostitutes smile at me, I felt my face flush and my stomach dance with the same butterflies I got as a teenager—I was hooked.

♦♦♦

When my friends fell asleep after midnight on our second day, I walked alone to the red-light district. I made my way around nervously, searching for the right woman. Many were old, large, or unattractive. I wondered how they even made a living when faced with much younger, much more beautiful competition.

But where was the competition? I began to think I was making a mistake.

Just after I had given up on the whole idea, an extremely attractive woman caught my eye and opened her door for me. With a head of thin, dark-brown curls, and a slim, toned body, she resembled a young Julia Louis-Dreyfus. I swallowed hard and went in.

The room was bathed in soft red light. There was a coat-rack, a small rug, and a bed the size of an operating table. But for the red bulb, the room felt like a hospital. It was clean and furnished for efficiency. I wasn’t about to have sex, I was about to be processed.

We shook hands. She told me her name: Mila. We talked. I asked her why she was doing this; she told me she needed to pay her way through medical school. I would have believed her if she’d told me she was a disguised space alien researching human sexuality.

I was stammering and stuttering. “Is this your first time?” she asked. I hoped I didn’t look like a guy who had paid for sex before. Of course it was my first time with a prostitute. “Yes,” I told her. It wasn’t until the next day that it occurred to me that she thought she was taking my virginity.

She asked what I wanted, and I suggested something, well, slightly exotic. “Two hundred euros,” she told me. Way too expensive. Perhaps I should have just backed out then, but she looked so kind. She counter-suggested “the usual” for 50 euros. “OK,” I said.

We made love quickly and joylessly. We didn’t kiss. Our arms touched a couple of times. Then it was over.

♦♦♦

I thanked her as I backed out of the small foyer. There is no obvious post-coital etiquette with prostitutes. She smiled, and for a second, looking at her, I believed everything was going to be fine; she was going to reveal that this had all been a dream, and I really wasn’t anything like the sleazy men in the rooms around me. Then, as I stepped backward through the door and onto the street, my heel hit the threshold, and I fell on my ass.

Mercifully, she didn’t laugh—she looked genuinely worried and asked me if I was OK.

Was I OK? I had just cheated on an intelligent, beautiful woman, just weeks into our relationship. My friends would judge me. I was judging myself already. I felt cheap. Shame washed over me. All this for one loveless orgasm?

She put her hand out to help me up, and I grabbed it. Yeah, I was OK. Still intoxicated from substances and adrenaline, I stumbled back to my hotel and passed out on top of the covers.

♦♦♦

Eight days later, arriving at Newark, I was a wreck. Various debauched activities had taken their emotional and physical toll. As soon as I was home, I called the girl I was dating, and went to her place. We spoke for about a minute before I blurted out, “I did it. I’m sorry. I did it.”

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She wasn’t pleased. I started crying. “You told me it was OK!” I yelled. “Well,” she said, “I didn’t think you would actually do it!”

She wanted me to leave, but I demanded that she let me stay, to try to salvage our relationship. The next day, she was still fuming. But to my amazement, she wanted to keep seeing me.

Over the next few months, my thoughts about her wavered. The usual stuff: did I really like her? Was she right for me? Did she make me happy? Every time I came close to thinking the answer was no, I couldn’t get past her caring enough for me to forgive me. What was worse, I knew that I wouldn’t have done the same.

After five good months, she told me she loved me. For the first time, I let go of my fear of commitment. The old instinct to sabotage my relationships was gone. I told her I loved her, too, and I felt liberated. I smiled for days straight. Rainbows formed and birds sang. I was happy.

Then she dumped me.

♦♦♦

On the two occasions we discussed our breakup, I accused her of finally dumping me because of what happened in Amsterdam. But she always denied it. She was never actually in love with me, she said, and she could only see it when I returned the sentiment. No, it wasn’t the prostitute. It was just me.

Maybe she was telling the truth. After all, for a young 20-something in New York City, the only thing scarier than a partner who is unfaithful is one who is too faithful. I’ve shied away from women simply because they said they liked me. It’s that old Groucho Marx bit: if she’s interested in me, sometimes I have to wonder what kind of mental disorder she has.

The more I think about it, the more I’m convinced: it was the very fact that I decided to go to a prostitute that allowed the relationship to last as long as it did. Had I tapped into the same insecurities that compel women to fall for jerks? In that moment, I was a complete and utter asshole. When I told her I loved her, and she didn’t have to battle her insecurities anymore, the excitement and attraction evaporated.

And at some point toward the end of the relationship, she had met someone else. He could’ve been an excuse to leave me. He could’ve been love at first sight. I’ll never know.

Sometimes I think about the woman in Amsterdam, and I wonder if she’s treating patients in a hospital, or if she’s in that same room, treating patients of another kind. I hope she remembers me—if only as the stammering, stuttering virgin who fell on his ass on the way out the door.

—Read Evan’s previous piece, “Protecting Your Balls,” here. Want to know when his next piece comes out? Sign up for our email mailing list.