At Al's 35th birthday, he wants a wife and kids, so Jill fixes him up with Ilene Markham. Al finds out that Ilene wants kids too, so he proposes to her on Tool Time. Randy and Brad write a letter to Mark pretending to be Isaiah Thomas, so Tim and Jill tell Mark to get revenge.

On Thanksgiving, for a perfect Christmas card, Tim builds a Christmas Village and has the family wear costumes.

Al doesn't want to come to dinner with the Taylors after Ilene has a dream about Tim riding on a golden stallion in tight bicycle shorts.

When Jill is having Ilene and Marie over, Tim goes fishing with Al to get out of the house.

After researching cosmetic surgery on the computer, Jill finds that Tim wants her to have cosmetic surgery. Meanwhile, Tim plays a computer game with the boys and the loser must clean the house.

Harry offers to sell Tim 20 percent of his hardware store (that Harry's brother is selling). Jill doesn't let Tim buy it, so Al decides to purchase it. When Al becomes obsessed with the store, this drives everyone crazy, even Ilene when he skips a date with her, and Tim decides to confront him about it.

After taping Jill's speech, he accidentally leaves the record button on when he critiques her speech. After Jill sees the video, Tim reads some of her psychology books and tapes a fake conversation with his buddies, complimenting Jill.

When Al is published as one of Detroit's "Most Eligible Bachelor" in a magazine, women begin flocking all over him and he starts to ignore Ilene. Mark has to write a report on the most interesting person he knows, and he writes it on Wilson instead of Tim.

Tim and Al scalp tickets to a hockey game when Tim can't go, but they get arrested and Jill and Ilene come to bail them out. Meanwhile, Mark paper maches Wilson's face when he watches the boys while Tim and Jill are gone.

Tim invites everyone over to the house for Jill's surprise birthday party, but Jill is off looking for her childhood piano.

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.

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.

When Al is the producer of a video, he selects Tim to direct, until Tim gets too bossy. Jill gets a computer.

Benny isn't allowed on the guest list fo the Thanksgiving dinner party at the Taylor house and Tim gets into the spirit of giving.

Before Al and Ilene's wedding, Al tells the guys a secret.