Takes place in the early 2000s, as a generation struggles to connect and define what it means to love and be loved. Six New Yorkers juggle love, friendship, and the looming adulthood. Sam Wexler, a struggling writer, is having a horrible day. Assisting a young boy separated from his family on the metro, Sam establishes a gratifying but complex bond. In addition to Annie, Sam's life focuses around Charlie and Mary Catherine, a couple considering moving to Los Angeles, and Mississippi.