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Jim's sister (Jennifer Coolidge) shows up on his doorstep -- pregnant.
Jim's sister (Jennifer Coolidge) shows up on his doorstep -- pregnant.
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S2, EP11 "The Brother-in-Law"Dana's new boyfriend (guest star Brad Paisley) is an amazing musician who can get Jim the gig of his dreams -- once Andy is out of the way.
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S4, EP19 "Take My Wife, Please"In order to avoid going to an opera with Cheryl, Jim asks an elderly widower to be her escort.
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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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S8, EP1 "The Blankie"Jim guilts the older kids into doing household chores after Jonathan's special blanket goes missing.
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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.
According to Jim
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.
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S7, EP15 "The Six Week Curse"Andy is sure Emily is going to break up with him, since all his former girlfriends left him after six weeks of dating; Dana hypnotizes Andy to find out the cause of his breakups.
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S7, EP14 "The Chaperone"After years of dating, Andy meets the perfect girl and worries that she will break up with him; Jim offers to take Andy's girlfriend's daughter to a concert with Ruby and Gracie.
