Plot: 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.
Alternative Plot: Lovestruck Dustin (Jason Biggs) is dating Alexis (Kate Hudson), his ideal girlfriend, but when she dumps him for coming on too strong, Dustin takes drastic measures to win her back. He asks his pal Tank (Dane Cook) to take her on a horrible date so that she will come running back to him, and Tank happily agrees. However, Alexis is more than a match for Tank's shock tactics, leaving him torn between loyalty to Dustin and a growing attraction toward Alexis.
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