Steven Goodson is your average twenty-eight year old guy toiling away as an accountant. His girlfriend Chloe (Andrea Bogart) is every guy's dream, a stunning model who takes your breath away. However, his happiness and his entire identity is shattered the instant he finds out that Chloe has strayed. Devastated, Steven turns for support to his best friend Jack Manning (Steven Pasquale), a cynical sell-out who's engaged to his boss's (Ray Baker) daughter (Amy Adams). Jack bluntly tells him the only way to get over Chloe is to go on a run and sleep with as many women as he possibly can.