The movie: The 40-Year-Old Virgin (2005)
The player(s): Steve Carell and Elizabeth Banks

Though Andy's (Carell) deflowering—and happily ever after—comes courtesy of Trish (Catherine Keener), he spends the bulk of the 116 minutes of this Judd Apatow classic fighting off the sexual advances of a bevy of interested female suitors, including up-for-anything Beth (Banks).