This article was the recipient of a Lisagor Award in Non-Deadline Reporting, Non-Daily Newspaper or Magazine, Circulation Above 20,000.

She grew up as Troy, a white, middle-class boy, in Urbana, a town of about 12,000 in western Ohio. Home life was always difficult. “Troy’s birth mother would take him to bars, leave him in public places,” says Donahoe’s adoptive mother, Kathy. “So he was put into foster care when he was 18 months old. We adopted him through foster care when he was almost three.”

Boystown has been a destination for LGBTQ youth since 1970, when neighborhood residents marched in Chicago’s first gay pride parade (which this year attracted an estimated 850,000 people). For many of those kids—especially the ones who’ve been rejected by their families—the neighborhood offers a new start. Or at least the hope of one.

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Late last year Chicago Public Schools reported 15,580 homeless students age 14 to 21, 10,684 of whom were living on their own, without a legal guardian. Those statistics aren’t comprehensive, though, since many students don’t report their homelessness. Nor do the stats include all of the kids who, like Donahoe, migrated to Chicago. According to the Chicago Coalition for the Homeless, the number of homeless youth has increased by 24 percent over the last two years—yet there were only 209 beds available for them in the city’s centers and shelters during 2011. And a 2007 study by the National Gay and Lesbian Task Force states that 40 percent of Chicago’s homeless adolescents identify as LGBTQ.

For all its perils, homelessness can be monotonous. Many of those afflicted by it find themselves stuck in a daily pattern. “Every night I try and get into the Crib at 8:30,” says 23-year-old Apollo Jones. There are only 20 beds at the Crib, a queer-friendly emergency shelter run by the Night Ministry, and those who don’t get one have few options. They might call friends, ride CTA trains, visit a bathhouse, head to “Ho Stroll” (a sex strip near Belmont and Sheffield where they can make quick cash), or just walk around until a drop-in center opens in the morning.

Walking along Broadway, Donahoe points out several shops where she does business. “The manager here is one of my clients,” she says, pointing to a by-the-slice joint. “I can always get free pizza from there.” Donahoe says she sees some johns several times a month and builds a rapport with them. A few even bring her breakfast.

Despite her swagger, Donahoe faces innumerable hazards. A study published in 2006 by the National Gay and Lesbian Task Force shows that all street-based youth, and primarily those who identify as LGBTQ, are severely affected by mental-health problems, substance abuse, risky sexual behavior, and abuse and violence.