On his way to a meeting with a publisher, aspiring novelist Sam Wexler (Radnor) finds Rasheen, a young boy separated from his family on the subway. When the quiet Rasheen refuses to be left alone with social services, Sam learns the boy has already been placed in six previous foster homes and impulsively agrees to let the boy stay with him for a couple days. Dropped into Sam's chaotic, bachelor lifestyle, Rasheen is introduced to Sam's circle of friends; Annie (Malin Akerman) who has an unhealthy pattern of dating the wrong men, as well as an auto-immune disorder which has rendered her hairless, Mary-Catherine (Zoe Kazan) and Charlie (Pablo Schreiber) whose potential move to Los Angeles threatens their relationship, and Mississippi (Kate Mara), an aspiring singer/waitress who tests Sam's fear of commitment. When Sam's unexpected friendship with Rasheen develops, he realizes adulthood is not about waiting for the right answers to get the life you want, but simply stumbling ahead and figuring them out in the process.