Navigating Sex & Strangers on Craigslist's Casual Encounters

For those who're attached or who're somehow virgins in Internet-facilitated or enhanced sex, it's worth pointing out that online dating is now the new norm, and frequently as tame as a house cat. But there's still a wild beast roaming out there and it's name is Craigslist.

The Craigslist casual encounters section offers a no-strings-attached experience that's expedient and anonymous. Where you can find someone with the same interests as you, meet up and move on. Where you can request and indulge your most banal or erotic fantasies without consequence (in theory) or investment (more theory). And where, if you're a certain way inclined, according to a Kinsey Institute scientist, you can find even more sexual enjoyment due to the anonymity factor.

Apparently, many people want some or all of those things (and get them, and go back for more of them). The section, which has a loyal "community" of followers as well as newbies, started in 2000 on the free classified website and now accounts for two per cent of all Craigslist postings, which run in 570 cities and 50 countries and get more than 50 million visitors a month. In fact, the New York Times reports that traffic to all Craigslist personals sections -- including the one for romance and the one for missed connections, where people try to find the hottie they saw on a train or across a crowded room -- is higher than for any other personals website including Match.com, eHarmony and Yahoo personals.

There are even how-to guides (for placing the ad and responding, not for what to do when you meet up).

But as one Savage Love column advised, "If something seems too good to be true, it probably is. On the Internet, that applies to: (1) offers for creams to help men 'grow extra inches'; (2) chain emails claiming that if you forward them, you'll get cash from Bill Gates/a big pharmaceutical company will give free drugs to a poor kid with cancer; and (3) Craigslist ads for no-strings-attached sex posted by women with pictures that look remarkably similar to porn stars or Lindsay Lohan."

So, yes, as with all things on Craigslist -- the "like new" mattress that turns out to be stained, or the reliable seller who isn't there when you show up for the $25 microwave -- there are more obstacles in the road to transactional bliss than the simple posting format suggests, and more barriers to honesty than a typical dating site or face-to-face encounter. And now, with the publication of Craigslist Casual Encounters: The Hilarious and Disturbing World of Seeking Sex Online (Haha Publishing), it's clear there are even more complications for those seeking simple satisfaction.

An anthropology of Craigslist

As the author, Henry Russell (a pseudonym), an L.A. lawyer who's posted dozens of ads, writes in the book's intro, "there are four groups of people within the Craigslist casual encounters community: (1) People legitimately looking to have sex with others, (2) Spam, or what some people call bots -- these are people that place ads or respond to them, trying to direct people to other pay websites for dating or pornography, (3) Prostitutes or 'masseuses,' essentially people looking for money in exchange for services, and (4) People interested in browsing the casual encounter ads, but not actually looking to meet people in person."

(The legions of sex workers and "masseuses" are fairly new to the section, according to the NYT article. In 2006, Nassau County set up a prostitution sting operation focused on Craigslist. As a result, last year, Craigslist reached an agreement with state attorney generals to charge a $5 fee and require a phone number for people posting "erotic services." The move led to an immediate 80 per cent drop in postings to that section, and turned the casual encounters section into a free-for-all.)