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