Ty, Hector, and Bao are close friends in a tough section of Boston, where they're called "the PG-13 crew." They're 14, decent kids with few skills who've bailed out of school. A small gang of older tough guys, led by Marcus and Tommy, menace them, and when the PG-13s fight back and rob one of the gang, Marcus and Tommy vow to kill them. They seek protection from Derick, a drug dealer, who agrees to help if they'll sell drugs. Meanwhile, Ty is recruited to work at a community center by J.J., its quiet leader. Ty and his friends are in a squeeze: surrounded by violence, drugs, and no opportunities, is there any way out?

Still living at home with his avant-garde actress mother, constantly rejected by art schools, and without a lover, aspiring painter Andrew decides to enter a contest in hopes of winning a six month stay in Kenya. Though things aren't great for Andrew, neither are they wonderful for his lesbian friend Lucy who constantly bickers with her lover Ingrid. Lucy complicates Andrew's life when she introduces him to the suspicious-looking, enigmatic Jerry.

Dumped by her loser boyfriend, Erin's love life hits rock bottom when her overbearing mother places an embarrassing ad in the "personals" section of a local newspaper on her behalf. Erin's disgust turns to curiosity as she searches for the right guy in a hilarious series of disastrous dates. Meanwhile, a lonely ex-plumber named Alan clumsily searches for his dream job while narrowly missing one chance meeting with Erin after another.