My Best Friend's Girl

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.