Curb Your Enthusiasm

Season 7 Episode 2:

Vehicular Fellatio

Larry deliberately tries to annoy Loretta, against the advice of a renowned doctor. Later, Larry dooms Richard Lewis' new relationship, and ends up profiting from Leon's indiscretion with the wife of a depressed pal.
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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...