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 will finding Lucas give Jamie everything she's looking for?