Eighteen-year-old Ian Lafferty (Josh Zuckerman) sets out on a cross country drive with his best friends Lance (Clark Duke) and Felicia (Amanda Crew) in order to lose his virginity to a red-hot babe he met on the Internet. The only catch: He has to drive 500 miles from Chicago to Knoxville to consummate the deal. But the journey, filled with hilarious misadventures, raunchy escapades and a buggy tow with an Amish farmer (Seth Green), teaches all three more than they expected about life and love.