Tim an Jill see Art, Tim’s old shop teacher who’s dating his mother, at a restaurant with another woman.
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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 detention during detention.
After Tim becomes threatened by one of Jill's classmates, he joins her book club.
When Tim has everyone at the house for Jill's surprise party, she is off looking for an old piano.
When Jill gets an A on her psychology paper, she starts giving psychiatric advice, which causes Michelle Russell's, Randy's girlfriend's, parents to have marital problems.
Brad throws a Halloween party for his new friends at school. Meanwhile, Tim, Jill, Al, and Ilene go to an awards show, hoping to win one for Tool Time, but it seems that the winner will be Cooking with Irma, which has won every other award.
Tim gets "the look" from Jill, after spending $4,000 on Pistons season tickets.
Tim turns the basement into Randy's new room so that Randy doesn't have to share a room with Mark.
Jill plans on having a romantic evening with Tim when they go to Chicago, but Tim's business meeting takes all day.
Jill, Wilson, and Al are angry when Tim gets an honorary Ph.D., but Tim later finds out that he got the Ph.D. because the college was going to use him, since he had a TV show, to receive additional funding.
When Tim's mother returns, she begins dating Mr. Leonard, Tim's old shop teacher, and doesn't want to spend time with Tim.
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 hires Marty to rebuild the Tool Time set, it puts their friendship on the line.
Brad feels jealous when Randy starts taking advanced classes at his school. Tim designs the man's bedroom.
Tim and Jill play each other in a tank driving competition, and Jill wins. However, Tim doesn't congratulate her because he thinks she humiliated him.
Jill wants Tim to get a vasectomy when they agree their family is complete. Meanwhile, Randy is voted "best butt" by the girls at school.
Mark wants to take flying lessons, but Jill doesn't let him. Jill takes piano lessons. Meanwhile, Tim and Al ruin Bud's car.
Dolores, Harry's wife, comes to Harry's Hardware and Tim's marital advice causes them to split up.
When a TV report is done on Tool Time, Jill gets angry when the reporter makes advances on Tim.
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.
After a medical checkup, the family finds Randy may have cancer.
Wilson becomes the director of Randy's school play but takes the fun out of it for everyone. When Tim later shows him the aluminum set he built, Wilson doesn't like it and orders him to rebuild a new one.
Tim an Jill see Art, Tim's old shop teacher who's dating his mother, at a restaurant with another woman.
When Wilson is burglarized, 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.
Al creates a Tool Time board game, hoping to earn enough money to propose to Ilene. But the game has problems and sometimes catches fire.