Four guys with a video camera and too much free time who tell the tale of one of their own and his quest to lose his virginity. Matt's the only one of the four who hasn't gone all the way - he was going to do it with his girlfriend on their two-year anniversary, until he found out she cheated on him and called it off. Now he's got some unfinished business and it becomes more important than ever for Matt to do the deed. His friends want to see him close the deal and lead him on a journey through friends with benefits, internet hookups, and even adult film stars - recording it all for the web.