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Tucker's Matthew embarks on a quest to scour the college dorm in which they met in order to track the mystery woman down. His M.O.: Posing as a maintenance man so he can sneak into the girls' rooms and try to match up a pair of panties she left behind in the elevator. And somehow this is meant to be charming.
Oddly enough, Matthew's antics are so kind-hearted and generally good-natured that it's hard to be offended by his voyeurism, burglaries, and crimes of passion. Along the road of his quest, Matthew of course helps a dozen or so of those 100 girls find a little more meaning in life. The ugly girl (Marissa Ribisi) turns beautiful. The pretty girl (Jaime Pressly) finds her inner self. He saves the alt chick (Emmanuelle Chriqui) from her mean old boyfriend. And he even gets to dress up like a girl!
This would all be a little more believable if Tucker didn't look like a 12-year-old Doogie Howser. His loverboy stunts don't really gel, and any parent would promptly transfer their kid to a new school if they found out about his activities.