Ian Lafferty can not seem to catch a break. He's taunted by his cocksure older brother Rex, shown up in the romance department by his 14-year-old younger brother and humiliated by his job at a mall donut shop. But Ian's biggest problem is that he's about to start college as a virgin. Now, Ian decides to set out on a cross country drive with his best friends Lance and Felicia in order to lose his virginity to a red-hot babe he met on the Internet. Getting nowhere with the girl of his dreams, Ian resorts to Internet dating. He soon hooks up with Ms. Tasty, a flaming hot blonde who can't wait to get busy. He has to drive 500 miles from Chicago to Knoxville to consummate the deal.