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• The only thing Stanley & Michael didn't plan on for the perfect date was...Phil.
• The only thing they didn't have on their perfect date... was any privacy

The clumsy and shy Stanley (Luke Wilson) is a nice fellow, beloved by his colleagues in the office. He has a crush on the gorgeous new-hire Diana (Denise Richards), but he has difficulties to get close to her. When Stanley finally invites Diana for a date, he hits the homeless Phil (Jay Lacopo) with his Taurus and his planned night turns upside down.