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True Stories: Casual Encounters of the Third Kind

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When you walk into a bar to meet a stranger you’ve propositioned through the now infamous Casual Encounters section of Craigslist, you expect to get, well, something casual. But after six hours of conversation, I had a hunch I had stumbled into something else.

Backing up, you might wonder what someone like me — an interesting, not crazy, mid-twenties professional — was doing in Casual Encounters in the first place. The answer was that I’d decided to keep my dating life on one side and move my sex life over to the other side. After a string of dating scenarios that all ended in complications or fizzled out after the point where one drink led to another drink, led to skirts getting pushed up over hips in the heat of the moment, I thought it would make things easier. If I could have casual hook-ups from which I could remain completely emotionally detached, then I might be able to date without rushing to sex. I could really get to know someone without being tempted to jump into bed.

Sexy e-mail exchanges and photo swaps led to a series of awkward, markedly un-sexy encounters.

That was the theory, anyway, and it seemed simple as I reeled in responses from my ad. As one of a few real live girls looking for a casual encounter, I had my pick of the hook-up litter. But sexy e-mail exchanges and photo swaps led to a series of awkward, markedly un-sexy encounters. I met up with a sad man who wasn’t over his ex-girlfriend, a stoned boy with overgrown hands and no idea where to put them, and a too-good-to-be-true army pilot who was indeed too good to be true. He lied about his age, education, sexual history, address — in short, everything. When I met these people in person, no matter how engaging our online flirtations had been, the reality never measured up to the fantasy we had created. No one was who they claimed to be, because with a few artful photos and carefully scripted e-mails, it was too easy to be whoever you wanted.

But after all that, I still couldn’t seem to let the experiment go. Opening my inbox to twenty new e-mails from men who all wanted me was too much of a rush, even if it was a virtual one. I’d been sucked into the weird world that is the Casual Encounters section.

When I got an email from a Scotsman seeking his Ph. D., who only had a few months left in town, I was skeptical but interested. He seemed different; he sent e-mails full of three-syllable words and void of indiscreet pictures. And he was in no rush get together, which made me even more eager, though after my numerous false starts, I wasn’t sure I wanted to have an actual casual encounter with him. Mostly, I wanted to understand how and why people did this: were they looking for the same thing I was? Could sex ever be so simple? Was anyone telling the truth about themselves?

I finally met him at a back table in a deserted bar one Tuesday night. When he opened his mouth and no Scottish accent came out, being that he was originally Canadian, I was a bit disappointed. When he informed me that he didn’t really drink, sipping on his Coke, I wasn’t sure why he had proposed we meet for a drink. But as we fumbled through the get-to-know-you questions, I realized he too was trying to figure out what other people were looking for, what I was looking for, what he was looking for.

When the bar staff finally kicked us out at closing time, we stood on the darkened street corner, swaying back and forth, not wanting to let the conversation end but not sure what to do. I watched him towering over me as he tried to figure out how he was going to bend down the foot between us to kiss me. I stepped towards him and back again teasingly, making it hard for him. Given the circumstances under which we’d met, I wasn’t sure if kissing him would indicate I’d go home with him. None of my previous experience with dating etiquette had prepared me for how this scenario worked. I did know that I wanted to see him again. He followed me to my car, nervously passing his umbrella from hand to hand, until finally, we couldn’t stand in the street anymore and I got into my car and drove away.

Regretting that I had kept him from kissing me, the next day I told him he should try again, knowing that I was drifting farther away from my plan to keep sex and romance comfortably separate. We met for dinner, which turned into drinks, which turned into kissing on the street corner, which turned into spending the night at his place, which turned into breakfast and then lunch and then plans for the next night.

I watched him towering over me as he tried to figure out how he was going to bend down the foot between us to kiss me.

Over the following weeks, I fell into a rabbit hole of long talks, not enough sleep, foot rubs, and eating ice cream from the carton. His basement apartment was like a hideout from my real life; in fact, for him, it was a vacation from his life back in Edinburgh. As much as I tried to postpone it, eventually I had to invite him over to my place, to see my real life. He checked out the photographs, artwork and books that were absent from his own temporary home. As we settled down onto my couch with takeout and a movie, things felt unsettlingly like an actual relationship.

Somehow we slipped from there into making plans to meet up after work, cooking dinner for each other, and carpooling in the mornings. At the height of our domesticity, he even fixed my laptop. For me, having someone in my space, brushing his teeth in my bathroom, taking up space in my bed, felt novel and strange — like a costume I was trying on to see how it fit. This was the closest I had been to a real relationship, but I was still holding back, knowing it was temporary.

One lazy evening, he asked me “What are you really afraid of?” After a few moments of silence, I managed to answer without making a quip, or turn the tables around with another question. I’m not sure I gave him the complete answer, but it was an honest one. Later that night, after a dinner of the worst Chinese food imaginable, we were strolling hand in hand in the darkness, and he said, “See, that wasn’t so hard. You opened up and it didn’t hurt.” I did feel exposed and vulnerable, but I just nodded my head in silence. “It was good practice for the real thing,” he added. I knew he was right. But by then, I didn’t want this relationship to be practice. I wanted it to be the real thing.

This was the closest I had been to a real relationship, but I was still holding back, knowing it was temporary.

And what was he afraid of? He’d been married at nineteen, and when I met him, he was twenty-seven with a divorce not even finalized. His wife had left for a supposedly temporary trip home to Canada and just never returned, raising suspicions of an affair. He was afraid that he was unlovable, that no one ever had or ever would love him unconditionally. Maybe what he’d wanted was less a casual encounter and more simple reassurance, proof that he was loveable.

I knew that he had come to the States on an academic fellowship to get away from his past life for a while, to experience being single for the first time since he was a teenager. Having been married for seven years, he couldn’t have been at a more distant end of the relationship-experience spectrum from me. The months and weeks we’d spent together were a tiny island in his romantic history, while they were a continent in mine.

Some weeks I did a better job at pretending that our routine was normal, pretending that he wasn’t leaving, pretending that I’d be fine when he did. Walking through the door of my apartment after a long drive home from Atlantic City, I blurted, “We’re home.” He smiled, glad that I felt he belonged there. But I wanted to retract it as soon as I had said it. I was home, but he was far from it. We were just playing house, and soon I’d be in my apartment alone.

Finally, the inevitable came. We were out of time. Lying in bed, with my head on his chest so I couldn’t see his face, I wanted to say so much. “Let me be the person who makes you know that you’re lovable. I can be that for you. I want to be that for you.”

But I couldn’t say that out loud. All I could say was, “I’m going to be sad when you leave.” Knowing there wasn’t much he could say, he pulled me into a hug. “Who’ll fix my laptop when you’re gone?” I asked, embarrassed that my façade of nonchalance had cracked.

“You’ll just go on Craigslist and find someone else to do it,” he joked. I tried to laugh but I knew I’d never be on Craigslist again. Whatever I was looking for now wasn’t going to be found in Casual Encounters — not a second time.

This article originally appeared in Nerve’s True Stories.