The Third Wheel is a 2002 American romantic comedy film directed by Jordan Brady and starring Luke Wilson, Denise Richards, Jay Lacopo and Ben Affleck. Its plot concerns 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).. The clumsy and shy Stanley is a nice fellow, beloved by his colleagues in the office. He has a crush on the gorgeous new-hire Diana, but he has difficulties to get close to her. When Stanley finally invites Diana for a date, he hits the homeless Phil with his Taurus, and his planned night turns upside down.
After a year spent working up the nerve, a man asks a sexy office colleague on a date - but when the big night arrives, a wacky homeless man suddenly enters the picture!. The Synopsis Clumsy and shy Stanley is a nice fellow, beloved by his colleagues in the office but woefully inept. With the aid of his roommate Mike, Stanley works up the nerve to ask out his alluring co-worker Diana. She agrees, but before the two can even be seated at a restaurant, Stanley hits a homeless con-man named Phil with his Taurus. Currying pity from the hapless Stanley, Phil.