My Dating Rock Bottom

“I’m sorry I’m late; it was murder getting this thing out of Barneys,” I heard a man’s voice pant as I caught a faint whiff of Marlboro Reds. We were at the Maritime Hotel, seated for a corporate dinner, and when I looked up, there-swaying, unmistakably drunk and almost two hours late-was my date.

I took in the full 6-foot-4 picture: the stained Hanes tee, the crossed eyes, the crumpled blazer complete with a security tag still dangling from its hem. I’m still not entirely sure whether he actually stole the jacket, but even without the aid of a comb, a shower and an iron, he was still impossibly handsome. And his very disregard for the stain on his T-shirt is what made him, paradoxically, so sexy. There are few things more intoxicating to women then a certain level of disinterest, and he had the act down pat. 

Sure, I was pissed about his lack of punctuality and vaguely horrified by his appearance, but a dimpled smile, perfectly placed hand on the nape of my neck and a wry, well-timed one-liner was all it took and I was putty.

Around this time I was on a particularly busy and ill-conceived dating bender. Trouble was, I had an open heart and a blind eye when it came to each of the lunatics I was attracting. Delusion, romanticism and a crippling weakness for hot assholes is a well-known trifecta. There was the Mormon Sociopath, the One-Eyed Hockey Player, the Firefighting Sushi Chef, Jay Z’s Security Guard, the Nipple Pierce Boy and a handful of run-of-the-mill commitment-phobes. I was at the end of my rope, but the Shoplifter had me tying the noose.

In dating, I am an optimist. Rather than secluding my flavors of the month to the privacy of a bedroom, I prefer to unleash them on my friends, family and employers whenever possible. “Isn’t he just adorable?” I’ll ask, gesturing to a guy with a full sleeve of tattoos and a missing left eye. 

We’d been hooking up on and off for about two months. This amount of time has a certain magic to it: It’s long enough to really get to know each other but short enough to wriggle out of an entanglement relatively unscathed. The end of the affair arrived about a week after I made the tragic mistake of inviting him to the aforementioned company party. I was sitting at my desk when my boss called me into her office; whenever this happened, it was rarely the occasion for good news. She swiveled her Apple screen around so that it faced me and there, splattered across a gossip blog, was a row of three different mug shots, all unmistakable likenesses of my Shoplifter. 

I was toying with whether to sob, vomit or commit seppuku when my boss’ voice interrupted. “Lindsey,” she said, “I never thought I’d have to say this to someone but … can you please not invite criminals to our client dinners?” 

I agreed, sadly knowing myself well enough to know that this may not have been a promise I could keep, and headed back to my desk to scour the blog post for myself. Turns out that while he may well have also had sticky fingers, his most recent bust was for solicitation and possession. He had allegedly offered an undercover vice cop prescription pills in exchange for her services.

What can I say? I just know how to pick ’em, I guess. I can assure you I did not take the news well at the time. In fact, my gay best friend Poodle notes it as the only time he’s ever seen me “totally and completely lose the fucking plot.” It in no way helped that the police report detailed his green rhinestone belt being unbuckled to reveal shiny black underwear. Was my crush a drunk, a drug addict, a thief, a hooker banger and a latent homosexual?

It is fairly self-explanatory why I now think of this episode as the rock bottom of my dating life. I was keeping company with a man better suited for the inside of a holding cell than a dinner party; I’d blocked out the voice of reason in my head; and my personal life was even starting to affect my work. This was no longer a comic case of “What did crazy Lindsey do this time?” Things had gotten dark and borderline dangerous. It took me months to fully recover (if from nothing else but the constant ribbing from pretty much everyone I knew), but recover I did. I vowed never to let things spin so far out of control again. Turns out doing a quick Google search on a guy before you take him out in public may not be such a bad idea.

My Dating Rock Bottom