[img id=”80191″ align=”alignleft”] The first time Lawrence sought sex with a stranger through the Internet, the novelty of the experience added to his excitement. The 25-year-old U of C grad student met “the nice married lady” at a restaurant near campus, and was pleased to see that she resembled the photo she’d e-mailed him: attractive and fit, if not exceptionally beautiful.

“You roll the dice every time, and the anticipation added something at first,” he said.

The pair chatted briefly to confirm that “we weren’t psychos,” and headed to his place, not hers: “I didn’t want to get macheted by an angry husband,” he said. They had sex, then a cigarette, and never spoke again.

Lawrence leads what he calls “a polyamorous lifestyle,” and prefers older women to college girls. They’re more sexually confident, he said, and less likely to “blur the line” between physical gratification and emotional attachment, which is problematic for a guy who likes to, quite literally, get in and get out. Lawrence says it’s “easy to love, but it’s just not easy to love one person.” He’s committed instead to near-anonymous sexual encounters with women he meets on the Internet.

But even here at the U of C, Lawrence isn’t alone. Anonymous sex, long sustained by an infrastructure of sweaty nightclubs and dimly lit bars, has gained a new apparatus as many young people turn to websites like Craigslist and MySpace to find partners for quick sexual gratification.

A brief perusal of Craigslist’s personal ads shows that U of C students are hopping aboard the trend. A recently posted “w4m” (woman seeking men) ad yielded hundreds of responses, and not just from a fringe segment of sexual delinquents: replies rolled in from U of C baseball players, successful alumni, science majors, frat boys, and even men claiming to be professors. New ads are posted every day requesting everything from oral sex in Regenstein to help someone “blow off steam,” as one poster put it, to requests for public sex in Ratner or the Divinity School. Some seek relationships, but for the most part, Craigslist posters want what they’ve termed “NSA fun”—no-strings-attached sex.

Though many view online personal listings, to use Lawrence’s words, “as the place where the weirdos come out to play,” some argue they’re no more scandalous than the one-night stands of the pre-digital age.

“It’s really not much different than meeting someone in a bar or at a party and bringing them home,” said a U of C alumnus who graduated in ’04 with a degree in computer science. He’s used Craigslist to organize anonymous sex on several occasions. “It’s just another medium to meet someone, but it’s more convenient. You can find people with your interests a lot easier than going through the traditional dating route.”

Lawrence, who has arranged over 30 sexual encounters online and who will sometimes meet up to three women per week, reiterated that anonymous sex is just an old practice that’s found a new conduit: “Do you really know someone you meet at a bar better than someone you meet on the Internet?” he asked. “Most of the women I’ve met are surprisingly normal.”

Convenience, he added, is a major draw of the Internet, especially since sex on the bar scene can mean footing a hefty alcohol tab. “At bars, you have to put in a certain amount of effort, dress nice,” he said. “You have to put on your game face.”

But often, in claiming there’s more to anonymous sex than mere convenience, people who’ve adopted this lifestyle do something one might never expect them to: they take the moral high ground.

They argue it’s a healthy way to express their sexuality, free from the alcohol and deceit wielded on the bar scene.

“[Using Craigslist] allows a certain directness,” Lawrence said, adding that both parties understand that the tryst will develop into nothing more than that, whereas people in bars sometimes woo one another with false hopes of a future relationship.

“Plus, I don’t dig the whole getting-drunk-as-an-excuse-for-doing-things-you-normally-wouldn’t-do thing,” he added. “I think it’s pretty stupid.”

Some Craigslist regulars insist their anonymous rendezvous have become a nuanced social practice, describing an entire etiquette system has evolved to ensure comfort and safety for all involved.

“There’s an amount of decorum at play,” Lawrence said.

The computer science alumnus said he usually meets his partners “in a more public place first” and chats a bit. “It’s usually just normal small talk…You chat a little to get to know someone first. [It’s understood that] you’re not going to talk about politics when you’re seeing each other for a certain reason.”

Lawrence said it’s also understood that both parties must send accurate photos of themselves before they meet. In fact, a misleading photo—one that depicts a 60-year-old man as the weightlifter he was in his twenties, for example—is a deal-breaker.

Once, when Lawrence walked into a café to meet with a woman who looked nothing like her photo, Lawrence felt little remorse in calling it off. After all, he said, “it’s not like we owed each other anything.” They had a cup of coffee and went their separate ways.

The computer science alumnus has his own methods for dealing with misleading photos: “I just tell them I have cold feet and back out,” he said.

Internet sex etiquette includes measures to promote safety.

“A condom is a must,” the computer science alumnus said. Lawrence said he gets tested for sexually transmitted infections every couple of months and presents all his partners with documents to prove he’s healthy. He added that he advises female friends who partake in anonymous sex to tell someone where they’re going as an extra precaution.

Some take safety one step further: they refuse to leave public spaces with their short-term partners. Sex in public places on campus appeals to both the sexually adventurous and those who feel more protected in public areas.

One U of C first-year grad student said he knew people who use the Reg as a “safe meeting place for casual sex.”

“If you’re meeting a stranger, no one has to know where you live and the surroundings are generally secure,” the grad student said. “The fact that you have to be affiliated with the campus to gain admittance is the first level of ‘clearance,’ so you know more or less who it is you’re meeting.”

In fact, personal ads by U of C members often set the stipulation of meeting in a public place on campus: “Anyone in the Regenstein looking for fun?” read a recent Craigslist ad from a man who wanted a “fun afternoon in the library.” (In true U of C fashion, third-year Ben Segal, who has never had sex in the Reg, said he could only condone the practice “if none of the books are damaged.”)

Nevertheless, many remain skeptical that seeking sex through Craigslist is a viable practice. Even beyond the obvious detractors who object to anonymous encounters altogether—and many people do—some say the Internet just isn’t a good way to find strangers for sex.

First-year Alex Foreman has attempted Internet dating but found little success. “A person’s [online profile] is a good representation of how they want their personality to appear, which makes it a terrible representation of their personality,” he said. “The things you really want to know—anything they don’t want you to know—you’re not going to find on the Internet.”