The Third Wheel is a 2002 American film directed by Jordan Brady, starring Luke Wilson, Denise Richards, Jay Lacopo and Ben Affleck. The plot of the movie revolves around a first date between the clumsy, shy Stanley (Luke Wilson) and the gorgeous Diana (Denise Richards), which is interrupted by a homeless man Phil (Jay Lacopo).
After more than a year fantasizing about asking out his co-worker, Stanley (Luke Wilson) finally asks Diana Evans (Denise Richards) out on a date. As the two venture out on their first date, Stanley hits a homeless man Phil (Jay Lacopo) with his car, and the events that follow are far from the night of romance that Stanley had planned. Meanwhile, Stan's co-workers, including his friend, Michael (Ben Affleck), are monitoring the date between Stan and Diana, and they are betting on how far Stan will get with the beautiful Diana.