Jim realizes that Cheryl has been spoiling their son Kyle for way too long, so he decides to make him a man by teaching him how to throw a perfect punch in self defense. However, things get out of control when little Kyle gets suspended for repeatedly hitting the school bully.

Jim ends up on a talk show after claiming that men shouldn't let women feminize them, and then goes to Dana's co-ed baby shower to prove his point.

Cheryl and Jim go to a motel in Indiana to celebrate their fifteenth wedding anniversary, but Dana's possible labor and a tornado interfere.

When Cheryl's beloved Uncle Donald dies, Jim takes over housekeeping, but soon starts to suspect that Cheryl is using him.

Cheryl persuades Jim to attend an anger-management class, but he soon learns that getting mad isn't as much fun as getting even.

Andy, Ryan and Jim are stunned when they find out that Dana and Cheryl recently appeared in a Chicks Gone Wild video.

When Dana gets into premature labor, and Ryan isn't able to come and deliver the baby because he is delivering a celebrity's baby, Jim has to be the one to deliver Dana's baby.

When Cheryl and Dana allow Jim and Ryan to take care of the kids and baby Tanner while they are out, things get out of control. Jim takes everyone to the museum and everything goes great until the Tyrannosaurus Rex display ends up destroyed.

While Ryan is away, Dana and baby Tanner are staying at Jim and Cheryl's, until Jim starts complaining about the presence of the baby, so Cheryl wants him to stay at Andy's for a while. While Jim and Andy enjoy their male bonding, Cheryl and Dana are enjoying their time together too. At least, until Ryan returns.

After an argument with a claims representative about his bill, Jim's health insurance is canceled, and Jim decides to hide the truth from Cheryl, until she ends up sick and he gets her cold.

Jim decides to toughen up his daughters basketball team and soon turns them from sweet and peaceful to an angry and aggressive basketball team.

Jim's bad softball game advice to Kyle turns to be Jim's worst nightmare when an Ghost of Andy visits him to show him the Adult Kyle's life as a loser.

Andy's new metal detector uncovers Jim's long-lost wedding ring, which causes headaches to Jim, because he bought a fake wedding ring as a replacement a long time ago so Cheryl wouldn't notice he lost it.

Andy and Jim end up in a war after Andy tries to sell him a grill that Jim gave him a few years ago.

After Tim and Cindy Devlin's sudden divorce announcement, Andy starts spending time with Cindy, which turns into a relationship, and an urge for Cheryl and Jim to break them up.

In order to avoid attending another musical with Cheryl, Jim finds a gay man to accompany her.

Cheryl throws Jim an unwanted surprise party for his 50th birthday, which Jim then sabotages, and then later reveals the real reason why he won't celebrate his birthday.