Jon is an aspiring musical theater composer who is hoping to deliver the next great American musical with his newest work, Superbia. He is given an opportunity to showcase it in front of a legendary composer. But in the days leading up to the workshop, he begins to be at odds with the most important people in his life: his fiancée Susan is pressuring him to settle down already, while his best friend Michael is trying to convince him to abandon his passions to become financially secure.
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Leo is a successful author who is experiencing a tough writer's block. Feeling the pressure to finish the new installment of his popular series of books, Leo swaps homes with his best friend, Ellie, for a period of time. During his stay at Ellie's place, Leo ends up meeting Matt, who helps him get out of his own way when it comes to writing something new and inspiring. Leo and Matt's newfound friendships turn into something far more meaningful, just as Ellie is experiencing a similar situation with Sam.