How Craigslist Dating Gave Me The Confidence To Date Offline

After almost two years of abstinence, I posted a new Craigslist ad this week. The ad was for a new roommate, as my current one is moving. But, the experience reminded me exactly what I found so appealing about the free bulletin-board service during the years I developed a serious addiction to carefully drafting and posting ads. Back then, I wasn’t using Craigslist to find a new microwave or couch: I was looking for a boyfriend.

Not a hook-up, not a cheap fling — a boyfriend. Which was enough to make me an aberration on the site, because the attitude behind Craigslist’s Casual Encounters section prevails across the entire personals site to some extent. I wasn’t against getting laid, but my real hope was to meet a like mind (with, fingers crossed, a decent bod).

There’s an art to writing the right Craigslist ad. You need a hook, a simple concept that will reel the right element in. A skittish and nerdy young woman seeking her own type isn’t necessarily very enticing, unless she’s writing ads themed around zombie invasion (“Seeking someone with a solid city escape plan and own shotgun”). Tricks like that drew in gentlemen who seemed likely candidates for handling my particular kind of crazy.

My Craigslist addiction wasn’t helped by the fact that at the time, I was working long dull hours at a series of desk jobs, the kind of jobs where any contact with the world outside one’s cubicle proved reassuring. Reading from emails from strangers — strangers who wanted to meet me! — was a balm against being slowly bored to death by the tedium of temp jobs. And, one of my best friends, Melinda, was in the same boat — the two of us ended up enabling each other into ever more outrageous anonymous taunts to Internet users, just daring them to email us.

During that period, we achieved the greatest coup one could ever imagine coup-ing when using Craigslist to hunt down men. Melinda and I collaborated one day on an ad based on a real-life problem I was facing — I had an upcoming family reunion, and no boyfriend to prove to my extended relations that I was just as successful as Engaged Cousin Allie. The ad we co-wrote, “Please help me prove to my extended family that I’m not a lesbian,” not only elicited over a hundred responses — but one of them was from a famous person.

Famous isn’t exactly accurate, in fairness, but he was co-starring in a critically acclaimed basic cable drama, and had previously appeared on another series I’d enjoyed, which definitely made him the most famous person to ever show an interest in dating me. There was something profoundly ridiculous about it, the fact that someone whose job it was to look good on television would be on Craigslist, and reply to an ad so insanely worded. But I couldn’t dwell on the insanity — instead, I just focused on trying to get him to meet me in person, if only because then I could say that I had.

In the end, I pushed too hard, and our first date never ended up happening. But, the possibilities that experience opened up kept me hooked for years to come. That’s the thing about Craigslist — it’s free and available to everyone. Anyone could be reading your ad. Including the right one.

The zombie invasion ad, one of my first, lead to three months with Jeff, a sweet-natured production assistant whom I forgave for his atrocious taste in comic-book writers, mostly because our TV favourites were properly aligned. (At that point, I was so sexually inexperienced that media preferences were all I had to judge potential compatibility on.)

Even though I quickly began to feel like the brains in the relationship, Jeff and I had fun together, and he taught me how a relationship’s give and take is supposed to work. Dating him helped me learn how it feels when two people are working well together — and how it feels when they aren’t. Dumping him was the first really mature relationship decision I ever made, one that made me feel like a proper grown-up for the first time.

Not to say that my 20s have been a bastion of maturity. A few years after Jeff and the zombies, I found myself stuck between a few different men. One in particular seemed to be using my feelings for him as a petri dish for experiments in cruelty, and, tired of being played, I decided I needed to feel like a player.

So, I asked Craigslist if anyone wanted to come over to my house and drink a bottle of wine with me. Not just any wine, though: Klingon Blood Wine, a souvenir picked up from the Star Trek experience in Las Vegas.

That ad didn’t get as many responses as I would have liked. (My friends figured that really nerdy guys had been too intimidated to respond.) But, I did meet Michael, a sweet giant of a guy who sent a witty reply and equally witty follow-ups. After a first date in a public place, I invited him to my place for a night of Star Trek movies and the promised wine. The wine, we finished. The movies, we didn’t — thanks to my booze-fuelled pounce upon him. It was one of the few moments in my life when I’ve felt completely confident in myself and my sexuality.

What's always a defining factor of my Craigslist use is this: I never respond to more than one or two replies, picking out the respondees who trigger just the right feeling. This kind of made me an asshole, I suspect, someone who added to the heaps of rejection men experience across all dating sites. But, it’s also given me a certain confidence in my own judgement, confidence I’ll admit I was lacking before I first turned to the site.

And, it made a romantic of me, oddly enough — a believer in fate as well as my own judgment, with an ability to read some text and get a good sense of the person who wrote it. That sort of certainty gave me the confidence needed to approach Charles, when I first saw him across the room at a friend’s birthday party.

It had never happened to me before in person, that kind of instantaneous recognition. But, Craigslist had given me a taste of what it was supposed to feel like, the knowledge that I’d found what I was looking for in someone else. That’s what let me trust it that day — what let me flirt heavily, meet his eyes, and strongly hint at how much I liked it when nice young men invited me out for a drink and a chat.

I was still sleeping with Michael then, as casually as when we first began four months earlier. I liked him well enough, but the fact that he was also a writer meant that our dates frequently devolved into shop talk, and the sex was never that exciting. He’d become someone I would call on Friday nights when I didn’t have plans, a back-up option for my social life (with perhaps an orgasm at the end of the night). I told him it was over the day after I’d slept with Charles for the first time, and just like with Jeff, it was a clean break, almost emotionless.

Over a year and a half later, Charles and I are still together. It’s love, and I know that because I know what a relationship without it feels like.

In my single days, Craigslist represented possibility. With the control and freedom made possible by the bulletin board, I was able to reach out to what felt like the entire world, asking just one person out there to like me. It never worked out with any of my Craigslist men; in the end, too many neuroses and not enough chemistry eventually cured me of my addiction. But, for teaching me about the opposite sex, about how to woo and be wooed, about the value of having confidence in myself, I owe all those men a huge debt.

Even the ones who sent pictures of their dicks. Even them.