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To make Cheryl feel desirable, Jim fakes a jealous rage in a restaurant and tries to teach Dana's date to do the same, but the lesson backfires when Dana fears her new beau is paranoid and possessive.
To make Cheryl feel desirable, Jim fakes a jealous rage in a restaurant and tries to teach Dana's date to do the same, but the lesson backfires when Dana fears her new beau is paranoid and possessive.
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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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S5, EP4 "Charity Begins at Hef's"When Cheryl wins two tickets to visit Hugh Hefner at the Playboy Mansion, she decides to take Dana instead of Jim.
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S5, EP5 "The Race"Jim tries to teach Kyle a lesson about quitting by running a 10k marathon, but he ends up cheating in the race.
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S5, EP6 "Anec-Don'ts"In an effort to outdo Cheryl's story about meeting Oprah, Jim makes up a story about his construction office catching fire.
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S8, EP18 "Heaven Opposed to Hell"In the last ever episode, Jim chokes on some food and finds himself on trial in heaven, where Andy represents the defense and Dana the Devil.
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S8, EP17 "Diamonds Are a Ghoul's Best Friend"Jim is haunted by a ghost when he buys Cheryl a diamond necklace that was taken off a dead woman.
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S8, EP3 "Andy's Proposal"Jim urges Andy to propose to Emily or risk losing her, but when he sees Emily dining with another man, he doubts the wisdom of his advice.
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S8, EP2 "The New Best Friend"When Dana, Cheryl's sister and best friend, moves away, Jim realizes he must find Cheryl a new friend as soon as possible.
