The pickup artist

You’d probably talk to her, too, if you saw her sitting by herself at a wine bar in Lakeview, sketching in her notepad or chatting up the bartender. There’d be nothing threatening about those bright, wide-set eyes, the trail of freckles sprinkled across her nose and her mouth curled in a perpetual half-smile. And if it were one of the 365 nights she spent out on the town from June 2007 to June 2008, Maria Scileppi would’ve been waiting for someone just like you to strike up a conversation.

When Scileppi moved back to Chicago in 2007 after quitting her job as an art director at a New York advertising agency, she was on the prowl for friends. Rather than dread this hunt, she made it a project to meet one new person every day for a year, establish what she calls a “real social connection” with every one of them and document the real-world “friending” by taking a picture and writing a story about each encounter. Scileppi’s tactics varied by day: Sometimes she’d go to a bar by herself; sometimes she’d find a group to join on Meetup.com or scour the “strictly platonic” and “men seeking women” personals sections on Craigslist; other times she’d meet the person at friends’ parties or networking events. Scileppi even found a few of her subjects while trying to meet Mr. Right on Match.com dates. “It’s always a little awkward to ask someone to sign a [image and story] waiver at the end of a date,” she says. “Or worse, after you’ve slept with them.”

So, how many actual friends did she get out of the project? “About 30,” she says. “Those are the people whose numbers are in my cell phone, who I actually see and hang out with.” Scileppi, now associate director of the Chicago Portfolio School—which helps students develop advertising and graphic-design portfolios—also collected hundreds of unforgettable stories. There’s the Iraq War veteran who had to down a fifth of vodka in a Starbucks bathroom before he could talk about how he accidentally killed a civilian family in Fallujah; the murderer just days out of prison who drank Scotch with Scileppi at Burton Place bar in Old Town; the TV actor (William Mapother of Lost) whom she met on a plane and had such intense chemistry with (“We were literally fighting over who would get to ask the next question”) that a brief romance ensued, complete with a weekend of raw foods and hiking in Hollywood. Once, she formed a sisterly bond with a stripper at the Admiral Theatre. “She gave me a lap dance, and I gave her a hug,” Scileppi says. Then there were the many artists, musicians, cab drivers, manicurists and friends of friends who all agreed to be photographed and logged as Scileppi’s “person” for a given day. On a few occasions, she got calls from past project participants saying things like, “Guess what? I just met your February 27!”

On June 13, FLATFILE Galleries (217 N Carpenter St, 312-491-1190) will host a one-night showing of the project titled “Peoplescape: A Year-Long Social Experiment.” (FLATFILE recently shuttered, so Scileppi’s renting the space.) Scileppi plans to invite all the participants to the opening. There’s also a book in the works. “This project was the hardest thing I’ve ever done in my life,” she says. “But it gave me an incredible sense of freedom. I met people, did things and went places I would have never considered otherwise. I said yes to everything.”

For more information about Peoplescape, visit peoplescape365.com.

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