Dustin, an amiable guy, is in love with Alexis, a coworker. When she tells him she just wants to be friends, he hires his roommate Tank, a fast-talking, amoral scoundrel who has a side business: men whose women have dumped them hire Tank to take their ex-girlfriends out on the date from Hell, to drive the women back into their old boyfriends' arms. He takes out Alexis who, against her better judgment, decides she needs some randy fun, so Tank is in a quandary: take Alexis up on her offer, or stay true to his friend. More complications ensue as the wedding of Alexis's sister approaches. Tank seeks advice from his father, Dustin pursues Alexis, and questions of self-worth need answers.
Dane Cook, Kate Hudson, Alec Baldwin, Jason Biggs, Diora Baird, Lizzy Caplan, Riki Lindhome, Mini Anden, Hilary Pingle, Nate Torrence, Malcolm Barrett, Taran Killam, Faye Grant, Richard Snee, Amanda Brooks