When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion in a charity-raising contest that Jim secretly entered her in, she decides to take Dana instead of him.

Out-of-shape Jim enters a 10K marathon to teach Kyle, who wants to quit basketball, a lesson about not being a quitter -- but he cheats to get first to the finish line.

Cheryl and Jim get into a disagreement about Erik Estrada, and Jim tries to prove that the incident that occurred ten years ago was not wrong.

Cheryl believes she's attending a tasteful lingerie party, but is shocked to learn the hostess is selling sex toys and Cheryl buys one, but won't tell Jim.

Without consulting with Cheryl, Jim transforms the garage into a cigar lounge and donates the kids' old clothes and furniture to charity. When Cheryl informs Jim that she is pregnant with twins, he is forced to retrieve all the stuff that he gave away, and has to deal with the fact that he is going to be a father of five.

The Devil himself visits Jim to remind him of the deal they made years ago, when Jim promised to give away his fifth child if the Devil helped him win over Cheryl.

When Dana, Cheryl's sister and best friend, moves away, Jim realizes he must find Cheryl a new friend as soon as possible.

When Cheryl learns of Jim's plan to use their twins in a movie starring Steve Guttenberg to get some money for Christmas gifts, she refuses to let him do it, but Andy and Jim decide to go through with the plan anyway, only to have it backfire when the producers cut the kids hair to make them look alike.

Cheryl and her friends, eager to get an afternoon away from the kids, arrange a "Daddy and Me" group for Jim and other dads with young kids at their home. Jim makes the best of a potentially boring situation by turning babysitting into a sporting event--staging baby races where the dads bet on their kids and drink beer.