Loveable underdog Ian (Josh Zuckerman) is the last American virgin. At least that's how it feels to him now that he's 18, about to go to college, and losing girls to his 14-year-old brother. Ian's always been the nice guy, the best friend... never the boyfriend.
But his luck finally seems to be changing when he meets Danielle. She's everything he's ever wanted in a girlfriend?fun, sexy, and she really likes him. There's just one problem. She lives in Knoxville. And he lives in Chicago. And she thinks he's the Brad Pitt lookalike he's pretending to be on Facebook. At the urging of his best friend, Lance (Clark Duke), Ian decides to confront his fear of rejection when Danielle makes him the offer of a lifetime: "If you drive all the way for me, I'll go all the way for you."
Accompanied by Lance and Felicia (Amanda Crew), whom Ian has a thing for, but she in turn has a thing for Lance, Ian takes off on a road trip in his brother Rex's (James Marsden) beloved car?without permission of course.