The Wind Beneath My Wingman

Jason runs into a college friend who has since dropped out of school, which brings him to question his own life path. After looking at his vision board, the only plausible thing left to achieve is to perform music live.
Never having heard his music, Maggie signs him up for open mic night at the bar, but then quickly regrets her decision. Meanwhile, Mark is stuck in a dry spell, unable to pick up a girl to save his life. With Jason off the market, Maggie suggests Mark get a new wingman – like Simon. But Mark quickly learns that Simon knows nothing about women.

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S01E04 - The Pot and the Pirate