Looking for Love in All the Site’s Places

By Joni Williams


Whether you’re shopping for homes or hamsters, boats or books—or just about anything in between—you’ll find it listed on the local Craigslist classified ad site. And that includes the one thing money can’t buy. Love.


The site’s Personals section serves as a kind of virtual singles bar with ads ranging from well-mannered Misc. Romance posts seeking Mr. or Ms. Right to blatant invitations for random, ahem, “meet-ups” in Casual Encounters.


But the hot spot is undoubtedly Missed Connections, where posters attempt to win a second chance with a specific stranger they’ve seen, but didn’t approach, in real life. Shrouded in anonymity and brimming with limited descriptions, the ads have a curiosity-piquing mystique that draws a high number of both posters and readers. And they’re not all looking for romance.


Longtime 99Rock personality Kevin McKay finds them so engaging, he’s made Missed Connections a routine part of his radio show, reading the posts every afternoon and often adding his own playful observations or advice. Likewise, Edie,* a professional woman in her 30s, said, “I love to just read them, especially the Missed Connections,” while explaining how she was initially drawn to the site.


But when she stumbled on a smoothly worded post by Henri, a geneticist and laboratory owner, she couldn’t resist replying. “He seemed really intelligent,” she says, before adding with a chuckle, “he was one of the few (posters) who didn’t make a grammatical error every other sentence.” After emailing back and forth, she was so taken, she agreed to meet him in person.


For Edie, it was shock at first sight. Despite having described himself as 5’ 6” with an athletic build, she found herself face to face with “this scrawny, beady-eyed, creepy guy who couldn’t have been more than four foot nine.”  And his lovely home she’d seen in photos? Turns out he actually lived in “an old camper in someone’s backyard,” too cluttered for her to even enter.


Instead, he escorted her into his “laboratory,” a junk-filled, dilapidated bus, where he opened a ramshackle cabinet drawer stuffed with cannabis and asked, “Do you wanna smoke some weed?”


After posting several ads, Dan also quickly discovered the people replying weren’t always who they said they were. “It’s mostly prostitutes, even in the most modest of ads,” he says, explaining how they initially pretend to be sincere about looking for unpaid romance.


When he did find someone he was searching for via Missed Connections he was initially thrilled, but quickly found it to be an ego trip—for them, not him. “They basically just want to verify it’s them that you’re talking about (in the ad),” he wrote in an email, saying it was “not so much exciting” when the discovery didn’t lead anywhere.


Not all of the replies to a Personals ad seeking participants for this story were from people genuinely seeking to meet that special someone. Some told far-fetched tales of one-time encounters, such as the poster who claimed one of the meet-ups “resulted in a stabbing and the other, bestiality.”


Another sought to describe his experiences in overly graphic detail. After getting shut down, he persisted with an invitation “in the spirit of research” to watch as he acted out a fantasy involving two women “and write about it.” The offer was declined.


Some of the responses, though, were sincere, courteous and occasionally humorous. Others were shy and reserved. Edie stressed she did eventually meet an honest poster who proved to be gainfully employed and genuinely nice, just as he initially indicated. Though romance never blossomed, the two have remained friends offline.


“He’s a great guy, just a little socially awkward,” she says, explaining his preference for meeting people online. Because Craigslist doesn’t require the type of preliminary questionnaires that matchmaking sites use, posting a Personals ad is quick and easy and allows for anonymity, even when replying.


Her friendship, however, was the only lasting relationship of any kind reported by our participants. But that doesn’t mean it hasn’t happened. As one user of an online matchmaking site who’s now in a serious romantic relationship points out, “Once you find someone, you’re not going to browse a singles site anymore.  Why would you?”


And yet, the site continues to attract plenty of people willing to post. And as long as they keep posting, there’s sure to be just as many—maybe even more—readers. If nothing else, it makes for good, quirky entertainment.


* Pseudonyms used to conceal identities.

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