It's Tim's birthday, and he plans to go to a NASCAR race. However, Jill purchased tickets for the two of them, plus Al, Heidi, and Wilson to go on a river-rafting trip. They go rafting, but Tim reserves a luxury trailer for sleeping.
Randy and his girlfriend Lauren are selected to go to Costa Rica for a school program to study the rain forests. Jill is upset and does not want him to go. Tim tries to fix things by telling Randy he cannot go. Jill is more upset with this.
Jill's sister Carrie stays with the Taylor's while in town for business. Tim's brother Jeff is over for dinner. Carrie and Jeff start seeing each other, and Jill does not think Jeff is good enough for her sister.
Tim and Jill have dinner with Al and Trudy, his girlfriend for one month. Tim and Jill find out Trudy is wealthy. For the one month gift, Trudy gives Al a 1966 Ferrari. Al uncomfortably accepts the gift, but then returns it.
For the first time, the TV ratings for Tool Time show that Al is more popular than Tim. Al decides to start doing promotions and Tim even helps him line up events. Then, Al hires a manager who tries to push too much too fast.
When Tim finds out Marty is separated from his wife and living in the back of Harry's hardware store, Tim invites Marty and his children to stay with him and Jill. Tim turns out to be a great father to Marty's twins. Marty gets jealous.
It's Christmas time, and that means decorating in Tim's neighborhood. Al is excited to decorate his home for the first time, and proves to be competition for Tim. Randy comes home for Christmas and finds things changed since he left.
Tim is writing a book for Binford Tools, and since Jill and the boys are away for the weekend, Tim tries to write while home alone. But since he is alone, everything distracts him. He starts to dream of wealth and fame.
Tim has Penn and Teller on Tool Time. Tim's die-hard fans thinks Tim is departing from the show's basics. Meanwhile, Tool Time films in Tim's home. Brad trips over a rolled up carpet and injures his knee, risking his soccer playing.
Tim hires a mechanic for his car who turns out to be a gorgeous woman. Driving her home, he is caught by a traffic cam in a compromising position with her. The ticket arrives on Tim and Jill's wedding anniversary, and Jill is suspicious.
Jill visits the gynecologist since she has a problem. Turns out she has a tumor and needs a hysterectomy. While everyone is concerned, it seems like it should be routine. Then, during the operation, problems occur. Tim gets scared.
Jill's operation is completed, and she has had a total hysterectomy. Jill is really upset at what this represents. Jill's mother visits to help around the house. Jill's mood swings are all over the place.
Tim takes Wilson to a hockey game for Wilson's birthday. Wilson wins $10,000 by sitting in the raffle seat. He wants a greenhouse in his backyard. Tim realizes the plans block the fence. He fears the loss of conversation with Wilson.
Harry is selling the hardware store. It comes as a shock to the guys that gather there for man talk and tools. Al owns a percentage of the store, and Tim buys the rest. The business starts slow and then grows more than they can handle.
Jill is anxious about defending her thesis and shares her thoughts with Tim. Mark records it on video. Marks turns in his video project and parents are invited to view all the students' work. Jill's professor is there and hears her comments.
Trouble starts when the Binford CEO (Bud) confiscates all "non-Binford" tools from the set of "Tool Time" in an effort to make Tim into more of a company man. He also dictates that the cast of the show wear Binford uniforms. This leads to the usual mess. Brad finds out that he is still up for soccer scholarship to college, despite a prior injury. Conflicts arise between Tim and Jill over whether or not Brad is ready to play in the upcoming game before the UCLA scout.
Binford Tools hires a new manager to oversee the Tool Time Show. He wants Tim to have more explosions. Tim is against this. And, Al proposes to Trudy. He takes his mother to dinner to break the news to her. She has a heart attack and dies.
Tim and Al do their final Tool Time show. Many of the past Tool Time guests appear. For closures: Heidi is pregnant; Wilson's fence comes down; Al and Trudy get married in Tim & Jill's backyard; Tim and Jill have second thoughts about moving.