True Stories: Casual Encounters of the Third Kind

On finding love where you least expect it.

By Rebecca Ende

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.

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.