Let’s say you’re a straight woman who just moved to New York. You’d like to meet a guy, but your friend circle is too small for set you up; you hate the bar scene; and you can’t seem to get a match on Tinder. In your dark night of the soul, searching for any connection at all, you turn to the Craigslist personals. Among the first posts you come across is from a self-described 27-year-old “single guy with no kids, living and working in the city.” It is headlined: “GOT BOOBS?”

These are the murky waters that Jamie Cricket Kauget dredges. Kauget, a Brooklyn-based artist, began reading Craigslist’s personal ads nine years ago, when she was in law school. (She’s a personal injury lawyer by day.) The vulnerability on display offered a satisfying contrast to the bluster and strained self-assurance that many of her classmates projected, and soon, she was following Craigslist like a soap opera, noticing recurring characters and vague storylines. Some frequent posters would continually reinvent themselves, presenting a series of new-and-improved identities; others would subtly refine their approach to self-advertising over time.

Six years after her initial voyeuristic attraction to Craigslist’s community of lonely lovers, Kauget began drawing them. In a small room at the Bushwick Open Studios arts festival this month, she displayed a series of funny and sympathetic paintings and line drawings of Craiglists personals posters—all of which were created from the photos that posters attached to their ads. (She’s never actually contacted her subjects.) The works are “studies in loneliness,” Kauget says, but they also make up a “pseudo anthropology project”—a survey of the culture of Craigslist courtship and all its attendant slang, mores, and rituals.

This interview has been edited for length and clarity.

Your Craiglist drawings are very funny, but not necessarily derisive. Do you feel any tension between laughing at these people and exploring their humanity?

I met up with a girl off of Craigslist when I was younger, and it was a really dark time for me, when I felt like an untouchable pariah in society. I’ve really been there, and I still feel that way three times a week. I think the only reason I can talk about having done it myself is that it happened a long time ago. If I was in it right now, it would be too painful.

Like you said, there’s a tension between emphasizing somebody and mocking them. I see a lot of myself in their bravado and eagerness to be liked, and also their difficulty in finding partners. Everybody who posts on Craigslist—for the most part, they are people whom traditional social networks have failed. They’re not meeting partners in real life, through friends. They’re isolated and they’re lonely. In a way, I started drawing them as studies in loneliness. I was feeling lonely myself at the time, so that was what I wanted to explore. The isolation.

I also enjoy them on a more detached, aesthetic level. I really like the poetry of Anne Sexton—this idea of elevating everyday objects into art. Like writing a poem about tupperware, or something. Every bit of trash that floats past our eyes, and every bit of weird cultural detritus, is potentially art. And you can always take something and try to make it permanent, try to redeem it.

I think the Craigslist guys are more extreme versions of everybody—what everybody’s dealing with: the internet, living with a lot of scrutiny, the desire to look good, anxiety about yourself. Being isolated by the internet, and seeking the cure for that isolation on the internet.

Tell me about some of the recurring characters you’ve noticed in your nine years of reading these things.

There’s a woman who started out saying really directly racist things, like “No black people.” And now she says “I prefer caucasians.” You watch people clean up their acts. There’s a guy who always posts these lighthearted ads, looking for women to do fun activities with him, and he changes. The title’s always something like “Booze, arcade games, and 420.” Or “Sushi, coke, and cuddles.” It’s like a soap opera, and I’ve been following a lot of people this whole time—nine years—and watching them evolve. Sometimes they change identities, but I can tell by their voice that it’s them. It’s sort of a community.

Why draw them, rather than take a screenshot of the ad and present that screenshot as an art object? What happens in the process of drawing a person?

I like the idea that you can see somebody’s history, or their life, written on their face. I try to capture that, and I think line drawings are good for the nuances of people’s faces. I’m trying to get across this weird mix of feelings and thoughts that you can see in their faces.

Every person is as rich in inner life as any other, and I’m especially interested in these macho New York bozos. These guys in their reflective mirrored sunglasses, their pumped-up arms. You think, What’s going through that guy’s head? Their inner world has to be just as textured and evolved as anyone else’s. But what is it? I think in those Craigslist ads, you feel like you can see it.

The cartoons don’t really work if it’s somebody self-aware. The people I draw, part of what draws me to them is that they have no self-analysis, or it’s just blatantly off: The guy who’s just staring soullessly into the camera, and the caption is just “I want to have sex with a lady at her house or another place.” Or the guy who just says “Want to give me a blow job?” or something, and he just thinks that women are going to flock to him.

They’re misguided in their self-conception—and in a smug way, and in a misogynistic way. And that’s why I don’t feel bad knocking someone like that. There’s a lot of sexism underlying a lot of the ads that I’m drawn to. This kind of Come and get it, ladies attitude. Theoretically, I have no problem with mixing and matching the photos and the captions, but I’ve never needed to because people who post the most ridiculous photos also have good, ridiculous captions. Every time. It is kind of a type, I suppose.

Craigslist posts are ephemeral, right? After a while, they just disappear from the site. So by drawing them, you’re also saving them from certain death.

They’re gone after seven days. That’s part of what I like about it. I’m memorializing something that would otherwise disappear. I think that’s part of why I like really drawing it, rather than a screenshot, and why painting it is even better: you take this valueless little flicker and turn it into something—this traditionally valued medium.

To this day, people still have a little bit of, Oh, an oil painting. Or, Oh, a drawing. They look at them more than they would look at a printout. It’s meant to last, and to say something. I’m pulling out this image, wading through this sea of filth, to say “Look at this. This says something about who we are as a society, and what our inner lives are like, and it’s worth paying attention to.”

The Brooklyn gallery Nothing Space will host a solo show of Kauget’s work in fall 2015. Images via Jamie Cricket Kauget. Contact the author at andy@gawker.com.