Keep it Casual

Craigslist’s Casual Encounters Section and the World of Anonymous Sex

  • Graphic Brandon Johnston

Many of us are probably familiar with the online classifieds ads website Craigslist. Whether you’re searching for a new apartment, selling your How I Met Your Mother DVD collection or looking for an anonymous way to meet someone to have casual sex with on a lonely Monday night, Craigslist seems to offer something for everyone.


According to the website’s “about” page, Craigslist was originally founded in 1995 as an email list of events taking place in San Francisco. Named after its founding developer, Craig Newmark, the service allowed users to interact with each other through email to organize events within the city.

User growth and demand led to the creation of more classified services, such as a real estate section, job postings and a buy and sell section. Increased user participation led to the eventual creation of the website we are familiar with today: Craigslist.org.

Craigslist now operates in 70 countries with more than 700 local sites.

Beyond offering classified advertising services, the website also includes sections devoted to personals and dating services.

Missed Connections, for example, allows users to write publicly visible anonymous letters to people they observed, but did not have the opportunity to introduce themselves to. The goal of posting an ad is that the person will see it and write a response to the poster—possibly resulting in a romantic connection.

Perhaps the most notorious section of the website is Casual Encounters, which allows users to post anonymous letters soliciting strangers for sexual experiences.

With colourful ad titles ranging from “[Young] and Full of Cum?” to “Your Sweaty Hole Licked Clean,” coupled with an overwhelming number of dick pics, the section can be somewhat jarring to newcomers.

Users post ads along with their age, desired meet-up location, and their sexual preference, signified by letters corresponding to gender. For example, m4m is a man looking for a man, w4m is a woman looking for a man, t4m is a trans person looking for a man, and so on and so forth.

Over time the site has section gained a lot of popularity among the LGBT community, as it is seen as a relatively safe way of exploring one’s sexuality while remaining anonymous.

Go Ask Anonymous

Alex* started using Casual Encounters in the summer of 2013, initially as way to counter to his depression.

“[I was] lonely, bored, and couldn’t meet anybody,” Alex said. “I think it was a pretty bad part of my life, because I just didn’t care. I think Craigslist was a response to it, because when you think about it, it’s kind of like the end of the ropes, because you just give up normal ways of meeting people and finding sex. It’s definitely a sign of depression.”

Over the summer he used the website frequently. He described most of his experiences as strange and often uncomfortable, though most of the people he met were not threatening in any way and only once did he feel in danger while on a date.

“[The] last time I did it, it was particularly bad. I went there and he turned out to be a speed junkie, he was fucking high on speed,” Alex said. “He was being crazy so I’m happy I left before anything happened. He locked the three deadbolts, I thought I was fucked.

“I was just like, ‘I gotta go, I don’t feel good,’ and he was super nice about it,” he continued. “It was still really weird. He was like, ‘Do you mind if I do a line of speed?’”

Most of the dates Alex went on remained one night stands, and he did not keep in touch with the people he met online.

“I saw one of them on the street with his mother, which was hilarious. He gave me the panic face,” Alex said, recalling the time he saw one of his dates downtown.

Although it’s impossible to say for certain how many people actually meet up for dates, Alex says the Montreal community is fairly large. He estimates thousands of active users each month. The Montreal page receives hundreds of postings each day alone, which support that belief.

Alex has since stopped using the service, citing personal reasons. Despite having admittedly uncomfortable experiences with the people he met, he remains optimistic about the potential for the website to be used positively if it were to be embraced by more people.

“I think it’s a really great thing, [but] people are prudes,” he said. “I don’t think sex should be so confined.”

*Name has been changed

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