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Pete has a chance encounter with famed magician Penn Jillette, who shakes his faith and inspires a questioning Pete to try living with abandon for one night.

As his successful two-month college comedy tour comes to an end, Pete, donning a new look and confidence to match, takes a college-age aspiring comedian, Jaboukie, under his wing. But Pete's return to New York finds him having an awkward reunion and a big audition at the Comedy Cellar that could change everything.

During a tour stop, Pete pays a visit to his parents and introduces them to Kat, who notices the uncomfortably close relationship he has with his overbearing mom. As he tries to keep the peace, Pete grows increasingly trapped between the two most important women in his life.

Pete jumps at the opportunity of a lifetime to open for John Mulaney at New York’s Town Hall, but the gig leaves him in an awkward situation.