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Olivia (Yesly Dimate) is a twenty-four-year-old abstract artist living in Boston. Warmhearted, witty, and sensible, Olivia is wholly dedicated to her art, spending every moment outside her job creating collages and daydreaming of how her life will be after achieving artistic success. Olivia hesitantly decides to move to New York in pursuit of an artistic career and community with her ambitious friend, Izzy (Jamie Eddy). In the process, she will be leaving behind her oldest friend, Madeleine (Monica Giordano), an aspiring short story writer facing the challenges of early artistry. At a dinner party hosted by Izzy, Olivia finds an original and unexpected connection with Phillip (Shazeb Fahim), a 'peculiar' philosophy student. By chance, the very next day, Olivia runs into Phillip in the beautiful courtyard of the Boston Public Library. Olivia and Phillip decide to put aside the reality of their circumstances and see one another again. Over the course of the fall, as her move approaches, Olivia must contend with the changing nature of her close friendships, as well as finding the courage to match her ambition and pursue her desires artistically, and in her relationship. Olivia's story captures the universal moment in which we've decided what we must do but have to find 'how' we're going to do it.