Jim is a devoted husband, father, and in-law. Jim learns he lacks the strength to leave his tearful six-year-old at school as he attempts to ease Ruby's separation anxiety.

Cheryl persuades Jim to abstain from intimate activities until their major getaway; Jim and Andy debate about the girls' treehouse.

Mr Feeney, Cheryl's 15-year-old cat, passes away, and she asks Jim to bury it in the backyard. However, Jim is really eager to attend the Bears game.

Jim hires Dana to purchase a present for Cheryl on their 10th anniversary. When Cheryl discovers that Dana has bought all her anniversary gifts for the past ten years, she gets upset, and Jim tries to make it up to her.

When Gracie throws tantrums, Cheryl punishes her by not letting her go trick-or-treating, but Jim sneaks her out to celebrate Halloween; Andy starts to believe that someone is stalking him.

When Jim and Andy set Dana with a perfect gentleman, even Cheryl subsequently develops a crush on him, causing a situation.