Josh Zuckerman, Amanda Crew, and James Marsden star in this teen sex comedy concerning an inexperienced adolescent who rounds up the gang for a road trip from Chicago to Knoxville after receiving a particularly enticing message from a girl he met on the Internet. Ian (Zuckerman) has just turned 18, and he feels like the last American virgin. He works at the mall donut shop, he's taunted by his womanizing older brother, Rex (Marsden), and he's even losing ladies to his 14-year-old brother. Having struck out time and again with his dream girl and longtime best friend, Felicia (Crew), Ian finally resorts to logging on and looking for a date online. In a stunning turn of events, Ian manages to chat up a beautiful blonde named Ms. Tasty, who's eager to be his first. She's fun, she's sexy, and she's everything that Ian has ever wanted in a girlfriend. The only thing preventing them from consummating their relationship now is the distance between them; Ian lives in Chicago and Ms. Tasty lives 500 miles away in Knoxville. But it's easy to pretend that you're someone you're not online, and Ian hasn't exactly been honest about his appearance in the first place. Still, he's sure he could charm Ms. Tasty all the same once he meets her in person, so he takes the advice of his best friend Lance (Clark Duke) and prepares to take Ms. Tasty up on her offer to "go all the way" for him if he "drives all the way" for her. But everyone knows that a road trip is no fun alone, so in order to keep him company on the road Ian invites Lance and Felicia along for the ride. Later, after stopping off to party at an Amish rave and facing a series of hilarious setbacks, Ian finally meets the girl of his dreams. Unexpectedly, things don't go quite as planned..