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.
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In an effort to outdo Cheryl's story about meeting Oprah, Jim makes up a story about his construction office catching fire.
Jim tries to teach Kyle a lesson about quitting by running a 10k marathon, but he ends up cheating in the race.
When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion, she decides to take Dana instead of Jim.
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.
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.
Despite Cheryl's reservations, Jim gets Kyle out of his first day of kindergarten to go see a Cubs game.
Jim scrambles to find a replacement when he accidentally knocks the minister unconscious with the car door on Dana's wedding day.
Jim and Cheryl's botched anniversary moments from years past.
Dana and Cheryl worry when their respective partners Andy and Jim decide to take up some dangerous adrenaline sports.
When Cheryl's respectable bachelorette party disappoints Dana, Jim and Andy treat Dana to a rowdy night she will never forget.
Confident Jim is crushed when he loses a hot-dog-eating contest to a petite woman, and Andy compounds Jim's sorrow by deciding to date the winner.
Jim and Cheryl adjust the clocks to get the kids to bed earlier so they can have more quality time together.
Jim is shocked to learn that his recently deceased friend will be buried with a rare baseball card he stole from Jim.
Jim is dismayed when he has to drive Gracie to spelling bee tournaments all over the state.
In order to avoid going to an opera with Cheryl, Jim asks an elderly widower to be her escort.
Jim is concerned that Kyle is going to grow up to be effeminate when he insists on wearing a Cinderella costume for Halloween.
Cheryl and Dana are forced to smash their way out of a locked garage because they ignored Jim's lesson on how to open the door from the inside.
Jim offers to give Andy an old barbecue grill, then decides Andy should pay for it.
Cheryl surprises Jim with a romantic evening, but it cuts into his planned TV boxing match.
Cheryl wants Jim to give up all his vices so they can try to have a baby.
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