When Jim and Cheryl preview a sex education video to be shown to children at Ruby's school, they discover that the boy in the video is Jim.

According to Jim

Sex Ed Fred

When Cheryl and Dana's mother, Maggie, visits for the holidays, Jim and Cheryl compete with Ryan and Dana for her affection.

The Gift of the Maggie

Cheryl urges Jim to meet an old girlfriend (Linda Hamilton) for lunch, but has second thoughts when she becomes convinced the woman has romantic intentions.

Lean on Me

Jim tries to blackmail Dana when he learns she is having erotic dreams about him.

The Dream

To teach Jim the value of communication, Cheryl does not speak to him for three days.

James and the Annoying Peach

Jim helps Andy pick up a beautiful woman at the bar, but she turns out to be crazy.

The Chick Whisperer

In an effort to outdo Cheryl's story about meeting Oprah, Jim makes up a story about his construction office catching fire.

Anec-Don'ts

Jim tries to teach Kyle a lesson about quitting by running a 10k marathon, but he ends up cheating in the race.

The Race

When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion, she decides to take Dana instead of Jim.

Charity Begins at Hef's

Jim fears that Cheryl's romantic expectations will increase as Ryan (Mitch Rouse) showers Dana with gifts, until he learns a secret about a special tape Cheryl may have made.

The Tale of the Tape: Part 2

The Tale of the Tape: Part 1

Despite Cheryl's reservations, Jim gets Kyle out of his first day of kindergarten to go see a Cubs game.

Foul Ball

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A loving blue-collar dad tries to adhere to family ideals.

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Jim advises Ryan (Mitch Rouse) on how to deal with fluctuating hormones when he announces that Dana is expecting.

S5 E22 | Belaboring the Point