At Jill's cousin's wedding, Tim tries to squeeze in sports for him in the boys. After Jill gets tired of writing her speech for the wedding, she decides to go water skiing with the boys and gets injured.
Bud Harper, Tim's new boss, wants to replace Al because younger viewers don't like him. Meanwhile, Brad gets detention on the first day of school and additional detention for misbehaving during detention.
Jill gets an A on her psychology paper and starts dispensing psychiatric advice. Unfortunately, this leads to marital problems for Randy's girlfriend's parents.
Brad throws a Halloween party for his new friends at school while Tim, Jill, Al, and Ilene attend a cable awards show. The Tool Time cast hopes to win an award, but it appears that Cooking with Irma will sweep the event as it has every other year.
On Christmas Eve, Tim and Al get stuck at the airport on the way to Binford's winter festival. Ilene makes Al choose between her and his mother. Tim and the boys beat Doc Johnson in the Christmas lighting contest.
When Tim and Jill go bowling with Bud and his wife, Tim tells Jill to lose because he's afraid his career will be ruined if they beat Bud and his wife. Meanwhile, Angela, Brad's girlfriend, sets her sister up with Randy.
Tim and Brad get into a fight over Brad's new haircut and the hot rod engine. Meanwhile, Randy doesn't want Jill to help him rehearse for an audition to play Romeo in a school play of Romeo & Juliet.
Wilson becomes the director of Randy's school play but takes the role a little too seriously. Tim and Wilson clash when Wilson attempts to make him rebuild the play's aluminum set.
When Wilson is buglarized, Jill orders Tim to put in a high security system. But instead of them having peace and quite in their house, things get worse when the alarms begin going off by themselves.