I decided to dive into Craigslist’s () “Casual Encounters” — a section made for no-strings hookups — to see if any of what I assumed about that virtual place was true. Is it populated entirely by perverted sexual deviants, serial killers, prostitutes and scammers as rumors insist? Or can two regular people really make the connection that the section’s name suggests?
I should admit that I had no intention to actually hook up with someone, should the opportunity arise, if for no other reason than it would be inappropriate and manipulative to an unwitting partner to do so and write about it. But it’s not a stretch to say that even if you abstain from the goal, spending a week on Casual Encounters can teach you a lot about human beings and how the web has changed how we pursue one of our most essential and important desires.
It goes without saying that the content of this article is not intended for children or those made uncomfortable by such topics. But if you’re interested, read on for the story of my seven days on Craigslist’s Casual Encounters — my failures, near misses, discoveries, insights and successes. Following that, I interviewed two women to learn how they used the site successfully for their own fulfillment.
I began with a listing announcing myself to the women of my city.
Each day I tried a different approach to see what would be most effective, though I never lied or posted fake photographs. One day my message was intended to be sweet and normal; I suggested starting with drinks and fun conversation to see if we had chemistry, then going back to my place to cuddle on the couch with a movie and see where that led. Another day, I described it as a rebound. In yet another, I explicitly detailed sexual activities and used very aggressive language.
Ultimately, only the “sweet and normal” was successful, even though very few posts by women had that same tone (more on that later). I received about a half-dozen responses each day. Most were scams, some were men, some were prostitutes, and just one was legit.
Barking Up the Wrong Tree
All the responses I got from real people on my first day weren’t from women — they were from men. I made it very clear in my post that I was only interested in women, but a large number of men chose to ignore that.
They all offered oral sex. I responded to them politely, saying, “Just interested in women, but thanks for the offer! Have a good one.” Most didn’t write back after that. One responded: “Really man, can be cool and relaxing.”
I began to suspect that no women actually used the site. The stereotype is that women are interested in relationships, and that only men would be interested in totally casual sex, right? We know that’s not true, though. In fact, I was inspired to write this article when a friend told me many of her female friends had owned up to using it.
But where were they? I was only getting messages from gay or bisexual men!
An Army of Scammers
Over the next couple of days, I actually received a lot of posts from women. Or at least, they said they were women. To be honest, I doubted the veracity of the claims.
It didn’t take long to realize that almost all the replies I received were scams. The situation is so severe on Craigslist Casual Encounters that posts by real women who are actually seeking hook-ups are often flagged for removal at the slightest cause for suspicion.
The most common scams are “safe dating” websites. An alleged woman will write a man saying she’s interested, but that because of the Craigslist-based serial killers and rapists in the news, she needs some extra assurance that it’s safe. If you follow the link she provides, the website asks you for your credit card number — y’know, so it can do a background check to make sure you’re not a criminal. Right.
What little luck I’d had so far. The week was half over and I hadn’t had a single bite. I decided I would have to take the initiative, so in addition to posting my own ads, I started responding to every ad from any woman who seemed at all interesting.
I cast a wide net in my searches, looking up posts by straight or bisexual women between the ages of 18 and 35 who lived anywhere in Chicagoland — a large metropolitan area that’s home to close to five million females. Most of the women wanted something very specific they couldn’t find in their normal lives: Someone to help play out a particular fantasy, someone vastly older than them or someone of another race.
Very few of the women who were advertising seemed to be looking for anything I would consider a “normal encounter.” Nevertheless, I tailored each response to whatever they were looking for. I typically wrote two or three paragraph replies and matched the tone of their own messages, then attached a couple of tasteful photos of myself.
I didn’t get a single reply from an actual prospect this way. It turned out that most of the ads were fakes from scammers, and quite a few fell into another category all together.
Don’t Does Cost a Thing
Prostitution is what made Craigslist controversial. There’s technically another section for that — “Adult Services,” formerly “Erotic Services” — but that’s not the only place you’ll find practitioners of the world’s oldest profession.
The prostitutes of Craigslist speak in code, but it’s not a difficult one to learn. They advertise “French lessons” — an odd thing to advertise under “Casual Encounters,” don’t you think? Well, it’s obviously a euphemism for something else. Many of the ads that weren’t from scammers were from prostitutes.
The ads are so obvious that it’s surprising the euphemisms are effective in fending off law enforcement. Then again, maybe they are law enforcement. What a mess!
Amidst all those failures, I had one near-success. A woman wrote in response to my sweet “cuddling first” ad saying she was in town for only a couple of months, and that she was frustrated she couldn’t find a relationship. When she sent her pictures, she looked plain but attractive.
We exchanged a couple of e-mails over the course of two hours, tossing back and forth lists of interests and the like. She made it clear that she wanted to meet up, and while she talked about starting slow, it was clear that it would indeed be a casual encounter. But when I suggested a time to meet — the last message from me before I would reveal myself and back out — there was no reply.
At least, not yet. The next day, she e-mailed me saying she was deeply apologetic and that she’d fallen asleep. She said she’d like to meet up sometime. So yes, there are women on Craigslist. Well, at least one!
The Other Perspective, Part 1: My Fake Female Ad
You’ve probably guessed by now that the experiences for heterosexual men and women on Craigslist’s casual encounters are quite different. I observed that for every ad a woman posts, there are at least 20 from men. If nothing else, that imbalance ought to alter the experience.
To get the female perspective, I did two things: I posted a fake ad as a woman to see what kinds of responses I would get, and I interviewed two women who have had success hooking up on casual encounters in the past. First, the ad.
“I just broke up with my boyfriend and while it was the right thing to do, it’s been rough because I still have all this physical passion and sexual energy and I don’t know where to direct it,” I wrote. “I feel this is the best way because I don’t want to hurt him by hooking up with someone we both know.”
As for potential suitors, I asked only that they supply a photo and “be attractive and not creepy.” I clicked “post” and waited. There was a five minute delay before my ad appeared, then I started receiving about one response per minute.
Most of them were careful to say “I don’t do this often.” Some were attractive, some weren’t. Some sent pictures of themselves naked along with the word “Hi.” Others wrote a single paragraph making it very clear just how normal and nice they thought they were, and included the sort of photo you would find on a Facebook () profile. There were a lot of expressions of sympathy over my fake breakup. I was hearing from men of all types, and it seemed I had my pick of the litter.
After about thirty minutes, though, my post was flagged for removal. I thought I’d made it look legit, but as we learned earlier, folks have good reason to be hawkish about scammers.
The Other Perspective, Part 2: Interviews With Craigslist Women
After the end of my test run with Craigslist casual encounters, I decided to get more insight into the female experience with the site by interviewing two women who said they had successes meeting up with men on Casual Encounters.
Their problem was the opposite of mine. They had too many options to pick from, but they both dealt with the numerous choices in the same way.
Both women ultimately responded to men who they felt put effort into writing long, personal messages as opposed to quick notes. Multiple paragraphs of insightful and relatable prose won out — but only after the initial test of physical appearance. One said that only 5 to 10% of the men who responded to her ad made it past the initial, picture-based judgment. Both said they immediately eliminated men who opened with pictures of genitalia — a very common practice. However, looks were important.
My favorite anecdote: One of the women I interviewed said she once had a crush on a client at her job, but couldn’t make a move without compromising her professionalism. However, she was looking through Casual Encounters and saw an ad from a man, and she recognized his writing style — it was her old client! She sent him a message to see if it was him, asking a question only he would be able to answer. He proved his identity and they ended up hooking up.
One of the women said she would go to Casual Encounters when she was looking for a very specific sexual experience — something you can’t always count on from a one night stand that starts at a club or bar. The other said her reasons could be summed up as “curiosity, boredom, and convenience.” She also said “it’s a safe way to reach out in ways you might be too shy to in person.”
“There are a lot of shady people, or at least people doing shady things on Craigslist,” one said. “But once you get over the embarrassment of actually posting or responding to something on Craigslist, it has the potential to be very rewarding. The trick is to keep an open mind and not have any real expectations. At the very least, it’s mildly entertaining.”
So What is Casual Encounters Really Like?
After all this exploration, I’ll say that Craigslist casual encounters is a place where people go to find very specific things from each other that they might not be able to conveniently locate in the real world. Some of those things are very alternative.
It’s a last, best hope for some people who are looking to make a personal connection, but it’s full of spam, unwanted attention, crime, and, well… crazy people. You might not find what you’re looking for, but you’re sure to find something interesting regardless.
Put another way, Craigslist casual encounters is a sexual microcosm of the rest of the Internet ().