In this raunchy teen comedy, a college ladies' man accepts a bet to sleep with every girl whose surname starts with a letter of the alphabet before graduation, with the higher payout going to those with rarer first letters. As he navigates his way through the bet, he finds himself torn between winning for his friends and falling for a girl who is different from all the others - literally starting with the elusive letter X. But when his roommate discovers the true nature of the bet, it sets off a chain reaction that threatens to ruin Miles' chances with his new love interest. Will he win the bet or follow his heart?