Perpetual man-child Mike (Jon Tenney) breaks up with his mature, pretty girlfriend, Anne (Suzy Amis), but doesn't have to dwell on it, thanks to Danny (Tom Sizemore) and Rick (John C. McGinley), both of whom share his immaturity and fear of emotional intimacy. Roommates in a Chicago house, they play an ongoing game called "Watch It!" involving pranks. But "Watch It!" stops being harmless fun when Mike's more soulful cousin, John (Peter Gallagher), moves in and takes an interest in Anne.
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