Curb Your Enthusiasm

Season 5 Episode 2:

The Bowtie

Wanda Sykes thinks Larry purposefully adopted a dog she deems 'racist', Larry falls off his pedestal as a friend of the lesbian community, and Larry hires a private investigator to uncover some information about his past.
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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...