Bob Tree (Tom Green
) is an extremely clumsy and accident prone guy, incapable of holding down a job. Bob has the best intentions with the worst luck, but he will not accept this as his destiny and decides to enroll in Butler School in an effort to refine his inept ways. Anne Smythe (Brooke Shields
), a single mom with two kids, is spinning out of control trying to balance a high maintenance boyfriend, a stressful job and unruly, bratty kids. A desperate Anne, in dire need of assistance, stumbles across one of Bob's old babysitting flyers and calls. Much to their delight, the kids find Bob to be a real pushover and convince their Mom to hire him fulltime. Anne is pleased when she learns Bob has attended Butler School and assumes she has found a trained professional to look after the kids, cook and clean. After fooling Anne into believing Bob is the calm, collected individual she needs, hi-jinks ensue.