Miles is a smooth and smart college-aged ladies' man who 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. Money and pride are on the line, and all is going according to plan until Miles comes face-to-face with the captivating Gabrielle Xeropolos, aka: The "X". She's everything he's ever wanted in a girl but he's torn between his feelings for her, and cashing in on the bet with his friends.