

A college ladies man accepts a challenge from his dorm buddies - sleep with the entire alphabet, A through Z, before graduation. The rules are simple: the rarer the first letter of the girl's last name, the higher the payout. All goes well until he falls for the "X". Now he's torn between his feelings for the girl and winning the bet for his friends.
Writing
The alphabet gimmick is genuinely clever structure
Acting
Jefferson Brown commits to full himbo earnestness
Director
Karl DiPelino
Trivia, insights & behind the scenes
This Canadian indie predates The Scarlet Letter trope revival in Easy A by three years, proving the alphabet-as-sex-diary concept was airborne in North American comedy.
Director Karl DiPelino never directed another feature; this remains a fascinating one-off artifact of mid-2000s 'nice guy finishes first' wish fulfillment cinema.