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According to Jim
Jim is a couch-potato dad and husband trying to achieve picket-fence ideals while keeping a firm hold on his manliness. His beautiful wife tolerates his childish antics because of his tireless loyalty to her and their three kids. Jim's penchant for taking the easy route in everything frequently backfires, landing him in comical situations.
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S5, EP1 "Foul Ball"
Despite Cheryl's reservations, Jim gets Kyle out of his first day of kindergarten to go see a Cubs game.

S5, EP2 "The Tale of the Tape"
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.

S5, EP16 "Get Your Freak On"
Cheryl thinks she is attending a lingerie party given by Andy's new girlfriend, then learns the hostess is selling sex toys.

S5, EP17 "The Grumpy Guy"
Jim learns that his neighbor (Julie Newmar) has written a series of children's books, modeling a grumpy old man on him.