Can you ever really go back to the past? After five long years of living with Derek, her former bad-boy-turned-metrosexual boyfriend, Jamie Ross finally reaches her breaking point. She's had enough of his sneering disdain for her second hand wardrobe, unusual family, and low-paying job as the associate producer of Chicago's sleaziest daytime talk show. When her new boss plans a segment on reuniting lost loves, Jamie remembers Lucas, her first love and the boy she'd lost ten years earlier. Spurred on by her gang of quirky friends, Jamie goes on a hilarious, disastrous, and life-changing hunt to track Lucas down. But are some loves best left behind?