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.