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The series was set in Chicago, about a naïve and soft-spoken man in his 20s named Josh Greenberg (played by Jay Baruchel), who finds himself in several surreal and awkward circumstances while trying to find love.

The series was based on a book of short stories, The Last Girlfriend on Earth, by Simon Rich, who was also the series creator, executive producer, and showrunner.

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Things work well at first but Josh's insecurities take over and he becomes paranoid and jealous of other men she comes in contact with, including Whitney's friend Tanaka (Fred Armisen).

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Mike takes Josh out to a club hoping to hook-up, however Josh is insecure and unsure of how to pick-up women.

Guest starring Sarah Silverman as Josh's right hand (voice), Eddie Pepitone as Josh's left hand (voice), and Tim Heidecker as a bartender.

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