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Jim develops a friendship with Dana's new boyfriend, despite the fact that the guy dumped Cheryl years ago.
Jim develops a friendship with Dana's new boyfriend, despite the fact that the guy dumped Cheryl years ago.
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S5, EP2 "The Tale of the Tape: Part 1"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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S5, EP3 "The Tale of the Tape: Part 2"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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S6, EP18 "Jim's Birthday"Jim tries to sabotage the surprise 50th birthday party Cheryl plans for him.
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S7, EP18 "The Devil Went Down to Oak Park"The devil (James Lipton) comes to collect on a deal Jim made with him back when Jim was courting Cheryl.
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S7, EP17 "No Bedrest for the Wicked"A chance meeting in the supermarket lets Jim in on Cheryl's secret: though she says the doctor told her to stay in bed, her doctor actually wants her to be active.
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S7, EP16 "The Cheater"Pregnant Cheryl wants to have a game night and play a game that she never loses, but Dana knows she cheats.
