Karen is a sex educator with an uncanny ability to find friends and fuck-buddies on Craigslist. In fact, that's where we met.

She tells me there’s a hidden goldmine of potential hookups in Craiglist's long catalog of “casual encounters,” — if you know how to make a good post, filter through the unsolicited dick pics, and respond to all your potential slampieces and soulmates.

Navigating the sexual opportunities of Craigslist isn’t much different from what we do on dating apps like Tinder, OKCupid or PlentyofFish — except there’s no filling out long profiles, getting addicted to making matches, or relying on bullshit compatibility scores.

For people like Karen, who find that apps require too much effort and are too dating-oriented to end in an easy hookup, Craigslist is the perfect solution. For people like Karen, the anonymity and the promise of sex with a total stranger is intensely hot.

“I started Craigslist-ing because I was single for the first time in a really long time,” she explains. “And at first, I just used it as a masturbatory tool. It was a prime resource for collecting dick pictures. After a while, I wanted to take it to the next level.”

That’s when she started seeking out “dates,” and mastering the art of the perfect post.


Karen highly recommends posting your own ad, rather than responding to others’ posts. Craigslist is a cesspool of spam, so don’t bother sifting through it yourself. Become the one who is desired, rather than the one doing the desiring, and let the horny strangers come crawling to you.

A quality Craiglist post needs to include a bit about you, a bit about your preferred partner, something about the kind of experience you’re looking for, and a little about your safety precautions. Be neither too vague, nor hyper-specific.

Let’s say you describe yourself vaguely, explaining that you like dogs, you like to stay hydrated, and your favorite color is blue. Anyone who reads your post will have no idea whether you’re a well-adjusted adult, a literate chimpanzee, or a mass murderer with a foot fetish. To appeal to the hidden gems, describe yourself in a way that portrays you as a unique human.

“My most successful posts — where I found people that I really connected with — listed a bunch of shit that I really like, and that as a whole, makes me an individual person,” Karen explains. “I also listed the most basic requirements that I need in somebody else.”

You know, like that they shower daily, don’t live with their mom or have taxidermy animal heads all over their walls.

On the other hand, don’t be too specific. If the only point you mention in your post is your extreme desire for spanking, that won’t lure in the cream of the crop. Act as if you’re also looking for engaging conversation, an authentic date or an ongoing relationship. The pervy sex stuff can come into play in more intimate conversations.


This likely cannot be stressed enough — many of your responses will be dick pics.

According to some estimates, a reasonable expectation for responses to a woman’s Craigslist post is about 40 percent dick pics, 40 percent illiterate men with poor spelling and grammar or a lack of anything interesting to say, 10 percent copy and paste responses from men who can’t be bothered to alter their pick-up spiel, and 10 percent well-written and articulate responses that address your post directly.

“Guys who are posting are going to have a much worse market,” Karen admits. Men will also see their fair share of generic replies and thoughtful responses, along with some scammers and spammers. If a woman looks too good to be true, it’s because she is.

Once you’ve narrowed down a match or two, write them back. Carry on an interesting conversation before making plans to meet, and “do not meet the person until you’ve seen at least 4 or 5 good pictures of them,” Karen says, "because the pictures start adding up.”

This isn’t just about meeting your superficial needs. “You start getting a better idea of who this person is. Not only what they look like, but the way they’re dressing, what environments they’re in and how they’re presenting themselves,” she says. “It’s important to be extremely picky.”


Safety is the number one concern when meeting up to touch a stranger’s genitals, so take all the right precautions.

If your match doesn’t mention their STD status or how they plan to have safe sex, explicitly ask them about it. You can show each other proof that you’re herpes-free, or put your foot down about wearing a condom.

Meet in a public place, tell a friend where you’re going, and text that friend with updates during the actual date so they can make sure you’re not being axe-murdered.

On your date, check the chemistry before seeking out a bed. If they have three more chins than you expected, it’s fine to tell them it’s just not feeling right.

Whatever kind of of companionship you’re looking for, Craigslist can almost certainly provide it. It might be considered the “erotic underbelly of society,” but for those who can learn how to navigate its sea of perverts, an endless trove of sexual opportunities await.