On Jim and Cheryl's 10th Anniversary, Jim pays Dana to buy him an anniversary gift to give to Cheryl. However, Dana buys a beautiful and touching charm bracelet, going over the spending limit in the process, and Cheryl finds out that all her anniversary gifts over the past ten years were bought by Dana.

It's Thanksgiving and Jim and Andy are going bowling. Cheryl doesn't like the idea very much, so she sends the girls with him. Jim has a perfect game, but just when he was about to bowl his final strike, the power goes off and he is left with either waiting for it to return or giving up being perfect. Cheryl surprises him by bringing the Thanksgiving dinner to the alley so Jim's family and friends can witness his perfect game.

Cheryl's mother is coming to visit them for Christmas and wants to stay at their house. Jim and Cheryl, however, prefer that she stayed at a hotel but don't know how to bring it up without insulting Maggie. After Jim tells Maggie that Cheryl wants her in a hotel, Maggie gives her grandma's pearl necklace to Dana. Cheryl's upset and goes to the airport to ask her mother' forgiveness, where she learns Dana only got the necklace because she doesn't have anyone in her life like Cheryl has Jim. Meanwhile, the girls think Andy is Santa.

Cheryl leaves Jim in charge of their kids and some other kids who were there to play with the girls during a Bears game. The next day, one of the kids mom calls Cheryl saying her daughter dame home repeating a swearing she heard from Jim. Cheryl apologizes for him and Jim is insulted that she always automatically takes the other person's side. Cheryl apologizes, and not too later Grace repeats the exact same word. Jim decides to teach her not to repeat it by making her say it non stop until she can't say it again. It works. 5 days later, at Ruby's ballet presentation, she slips, falls and says the word, unmasking Jim's guilt.

Jim and Cheryl agree to let Ruby model for a print ad as a one-time thing, but when the photographer calls her a natural, Jim gets Ruby an agent.

Cheryl decides to go behind Jim's back and loan Andy $1,000 for a downpayment on a new condo.

When Cheryl has a revealing photo of herself taken as a Valentine gift to Jim, he proudly shows it to all his friends.

When Cheryl reminds Jim that she beat him at racquetball years ago, he claims he was only letting her win to gain her affections, so Cheryl challenges him to a no-holds-barred re-match.

After Jim is diagnosed with high blood pressure, Cheryl decides to do everything to help him. She makes him special food, give him backrubs, and keeps asking about his day in order to free him from stress. But Jim doesn't know how to share so much and tells her an old financial problem of the firm. Cheryl stays up all night doing math to figure out a way out of the problem. Jim says she has a disease and is always trying to help people, which Cheryl responds with stop caring about him. In the end, they finally settle their issues when Jim says he loves her and would be a total mess without her.

When the new DVD player breaks, Jim must find the receipt in order to exchange it. He can't find it anywhere and blames Cheryl of losing it. She says he was the one who lost it, and in order to "win" the fight, Jim buys another DVD player and tells Cheryl he exchanged the broken one. Later, Dana shows up with the receipt, in which Cheryl wrote her a recipe, and Cheryl - after realizing it was her fault after all - burns it. They get into a fight but soon decide to drop the point scoring and just be happy again.

Jim has a run-in with an old friend from his wild and crazy days who is now a cop. Jim sets out to prove he's not an 'old married guy' by staying out all night and partying. Unfortunately, this has bad consequences for both of them...

Jim agrees to take the girls for the day while Cheryl and Dana go to a doctor's appointment. At the park, Jim leaves the girls with another mom and goes to the movies... where he's busted by Cheryl. Things go from bad to worse when he tries to retrieve the kids and can't remember who he left them with.