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."
In the spirit of such classics as American Pie, "he Sure Thing and Superbad, this wild romp follows Ian, Lance and their third musketeer, the spunky and gorgeous tomboy, Felicia (Amanda Crew), as they set out in Ian's older brother's beloved '69 GTO. Despite many hilarious setbacks on the road, including a stop-off at an Amish rave (who knew the Amish could party?), Ian finally meets his dream girl...; but things don't turn out quite as planned. Along the way, Ian discovers that while he's prepared to go the distance for sex, there might be something even better a little closer to home.