Curb Your Enthusiasm

Season 7 Episode 1:

Funkhouser's Crazy Sister

Larry attempts a preemptive breakup with an ailing Loretta, and learns with Jeff that you can't make an 'empty gesture' to a Funkhouser.
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About Curb Your Enthusiasm:

He's got it all: a loving wife, good friends, a successful career, a great home...what could possibly go wrong for Larry David...