On the set of Tool Time, Al is a little upset with Tim due to some jealousy he harbors over the fact that his girlfriend Ilene had a sensual dream about Tim the night before. Because of this, he turns down Tim’s offer to have them over for dinner. Cooler minds prevail, and Al and Ilene do show up, only to have Tim try to diffuse the tension with some humor, but inadvertently embarrassing Ilene, and making her angry at Al for betraying her trust by telling Tim.
Randy is challenged to a sled race down Dead Man’s Curve, and loses. Despite Jill’s pleas for him to abandon further challenge, Randy convinces her that his pride and self-worth is at stake. Meanwhile, Brad abandons his saxophone lessons at any cost.
It’s Christmas, 1993, and it seems like any other Christmas time – Tim is preparing for the neighborhood Christmas light competition against Doc Johnson, Jill is prepping Mark for his big debut as the N in the Hamtrammick Christmas Noel Choir Singers, Randy becomes the helpless victim of Doc Johnson’s daughter Lauren, and Brad is ready to abandon it all to go skiing with his friends. When Tim and particularly Jill tell him ‘No’, he gets all huffy and refuses to go to Christmas mass, much to Jill’s dismay as she proclaims “family is always together at Christmas.”
When Jill Taylor (Patricia Richardson) gets a last minute invitation to her 20-year high school reunion, she’s eager to go in order to face off against her ex-best friend, Joanie, who stole her high school sweetheart, Jack. When they arrive in Washington, D.C., Jill almost loses her nerve, but Tim (Tim Allen) encourages her to sit down and talk with Joanie – where she learns some surprising news and gains some much-needed closure.
Back home, Al Borland (Richard Karn) is struggling to watch the boys for the weekend. When Randy (Jonathan Taylor Thomas) locks him out, Al gets a little advice from Wilson (Earl Hindman) in their first ever conversation.
It’s Thanksgiving, that time of year when the family gathers around to dress up in ridiculous costumes and pose for Christmas cards that they’ll never live down. Tim, inspired by a drive past the lumber yard, has been struck with a big idea to construct the perfect winter wonderland setting and expects Jill and the boys to dawn festive costumes, but when his more power solutions send the snow blower through the living room window, Jill puts her foot down on any more of his shenanigans, as she scrambles to finish preparing for Thanksgiving dinner.
Meanwhile, on Tool Time, Tim and Al construct the perfect Man’s Bathroom. Why? Because masculinity needs a monument to itself.
When Jill’s (Patricia Richardson) mother notifies her that three $50 bonds she bought for the boys have come due, she decides to let Brad, Randy and Mark (Zachery Ty Brian, Jonathan Taylor Thomas, Taran Noah Smith) figure out what to invest them in. When the boys decide to invest in a baseball card, Tim (Tim Allen) takes them to a toy store to make the purchase – but instead the three wind up buying an expensive remote controlled racecar signed by a famous driver. At home, the boys prove unable to keep their hands off this mint-condition keepsake and wind up severely damaging it but trying to hide it. When Tim and Jill discover the damage, they teach the boys a lesson by telling them that a buyer wants to give them $750 for the model – an offer the boys painfully turn down.
Meanwhile, Tim and Al (Richard Karn) go to a job site with the K&B guys to talk about how best to work on the high steel. Things get off track when Tim attempts to zipline down to an outhouse.