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Seizoen: 6 - Aflevering: 7 / 122 - Eerst uitgezonden: 10 november 2008 

Alan tries to get away from Judith. Meanwhile, Charlie and Herb go out on the town.

Seizoen: 6 - Aflevering: 8 / 123 - Eerst uitgezonden: 17 november 2008 

Charlie's new girlfriend Chelsea asks him to spend the night at her place, which puts Charlie well outside of his comfort zone, while Alan tries to enforce a punishment on Jake initiated by Judith for mooning a group of girls.

Seizoen: 6 - Aflevering: 9 / 124 - Eerst uitgezonden: 24 november 2008 

Charlie finds himself in an uncomfortable position when Jake takes off with the daughter of a former NFL player. Charlie's Mercedes proves a boon to Alan's love life.

Seizoen: 6 - Aflevering: 10 / 125 - Eerst uitgezonden: 08 december 2008 

Evelyn offers to pay for Jake's college education, and Alan becomes listless because he has no compelling reason to work anymore, while Jake discovers a hidden talent in the culinary arts that may allow him to bypass college altogether.

Seizoen: 6 - Aflevering: 11 / 126 - Eerst uitgezonden: 15 december 2008 

Charlie finds himself re-examining his wild ways when an old friend dies and begins to feel that his time on Earth may be drawing to a close.

Seizoen: 6 - Aflevering: 12 / 127 - Eerst uitgezonden: 12 januari 2009 

Charlie and Jake fight for the affections of a waitress, while Alan fights sexual tension with his receptionist.

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