Cassidy Harper (Virginia Kull) is a struggling actress sleeping on her mother's couch (Marilu Henner) and grinding out auditions, fearing that any chance at stardom may have already passed her by. Desperate to save enough money to move to Hollywood, she takes a job working as a runner for her mother's boyfriend (Ed Begley, Jr.), an importer in Chicago's diamond district. When she realizes the money is trickling in too slowly for her to put a stake together, she conspires with the owner's son (Ashton Holmes) to stage a robbery and keep the diamonds - using her former boyfriend (Zach McGowan) as the fall guy. Their hare-brained scheme only gets more complicated when she realizes she's still in love with her volatile ex.