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Judith is dating Jake's pediatrician (Ryan Stiles), and Alan is upset until Charlie points out that if she remarries, his alimony payments will end.
Judith is dating Jake's pediatrician (Ryan Stiles), and Alan is upset until Charlie points out that if she remarries, his alimony payments will end.
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S2, EP23 "Squab, Squab, Squab, Squab, Squab"Alan is reluctant to leave Jake with Evelyn for a sleepover visit until he finds himself partying with Charlie and a busload of beautiful female volleyball players.
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S6, EP4 "The Flavin' and the Mavin"Alan awaits disaster as Charlie romances Alan's sweet receptionist.
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S2, EP24 "Does This Smell Funny to You?"Charlie unknowingly sleeps with an elderly man's (Orson Bean) hot trophy wife.
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S6, EP5 "A Jock Strap in Hell"The guys run into Jake's former teacher (Alicia Witt) who became a stripper after a fling with Charlie; Charlie gives her a room and a job to try and help her out, but things get out of control.