The film opens with two small-time crooks Tommy Uva (Pitt) and Rosie DeToma (Arianda) getting high and robbing a florist on Valentine's Day. Tommy holds up the cashier with a pistol while Rosie waited in the car she inherited from her father. Tommy is arrested and sent to prison for 18 months. In the meantime, Rosie gets a job at a debt collection agency run by Dave Lovell (Dunne), who went to jail for bilking major companies out of $800,000 through fraudulent invoices. Lovell reformed his life and mainly hires ex-cons at his firm. He is happy to give Tommy a job and a second chance. Tommy is restless and instead of following the call script, he often counsels people on how to defraud Lovell's company.
