“The real freaks come out on Craigslist,” says Koester. “There’s a purity to it.” Even still, the site is a little tamer than it used to be: Craigslist shut down its “casual encounters” ads and took its personals section offline in 2018, after Congress passed legislation that would’ve put the company on the hook for listings from potential sex traffickers. The “missed connections” section, however, remains active.

The site is what Jessa Lingel, an associate professor of communication at the University of Pennsylvania, has called the “ungentrified” Internet. If that’s the case, then online gentrification has only accelerated in recent years, thanks in part to the proliferation of AI. Even Wikipedia and Reddit, visually basic sites created in the early aughts and with an emphasis similar to Craigslist’s on fostering communities, have both incorporated their own versions of AI tools.

Some might argue that Craigslist, by contrast, is outdated; an article published in this magazine more than 15 years ago called it “underdeveloped” and “unpredictable.” But to the site’s most devoted adherents, that’s precisely its appeal.

“ I think Craigslist is having a revival,” says Kat Toledo, an actor and comedian who regularly uses the site to hire cohosts for her LA-based stand-up show, Besitos. “When something is structured so simply and really does serve the community, and it doesn’t ask for much? That’s what survives.”

Toledo started using Craigslist in the 2000s and never stopped. Over the years, she has turned to the site to find romance, housing, and even her current job as an assistant to a forensic psychologist. She’s worked there full-time for nearly two years, defying Craigslist’s reputation as a supplier of potentially sketchy one-off gigs. The stigma of the website, sometimes synonymous with scammers and, in more than one instance, murderers, can be hard to shake. “If I’m not doing a good job,” Toledo says she jokes to her employer, “just remember you found me on Craigslist.”