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Josh Radnor makes his writing and directing debut in this romantic comedy drama in which he also stars. When young Rasheen (Michael Algieri) gets lost on the subway, writer Sam (Radnor) befriends him and takes him to his apartment. Soon the problems faced by those important to Sam become apparent: his friend, Annie (Malin Akerman), is struggling to deal with her alopecia, his cousin, Mary Catherine (Zoe Kazan)'s relationship with boyfriend Charlie (Pablo Schreiber) comes under strain as they discuss a possible move to Los Angeles and Sam's crush, waitress Mississippi (Kate Mara), is trying to make it as a singer. As they each work through their separate issues, they are all linked by their common search for love and happiness.

Sam (Radnor) is a struggling writer who has trouble with long-term relationships; one day while on the subway, he meets Rasheen (Michael Algieri), a young boy who has been abandoned by his parents. Sam takes the boy in, which gives him a preview of parenthood but also proves to be more complicated than he expected. Sam is infatuated with Mississippi (Kate Mara), a bartender with a dream of making it as a musician; tired of one-night stands, she agrees to move in with Sam for a few days to see how she feels about a "real" relationship, but Rasheen's presence makes things awkward. Another of Sam's sometime girlfriends is Annie (Malin Akerman), who suffers from a rare medical condition that prevents her from having any hair. Though she's beautiful, Annie's lack of hair has caused her to have a dire self-image and she jumps from one relationship to another with a handful of men, some of whom treat her poorly. And Mary Catherine (Zoe Kazan) and Charlie (Pablo Schreiber) are a couple whose relationship is teetering on the brink as he considers a lucrative job offer in Los Angeles while she refuses to budge.