Your Pic Gets Mine

How dating on Craigslist helped me find true love.

By Rose Mailer

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 has 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 couping 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 favorites 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.