Awkward, lanky, and self-loathing, 18 year old Greg Gaines (Thomas Mann (actor)), who describes himself having the face of “a little groundhog”, is a senior at Pittsburgh's Schenley High School who appears to drift through life while only seeming to broadly associate himself with the various cliques within Schenley's halls. He learns that a fellow student and former childhood friend of his, Rachel Kushner (Olivia Cooke), has been diagnosed with leukemia and is forced by his parents (Nick Offerman and Connie Britton) to befriend her in her time of need. Despite an extremely awkward first encounter on Rachel’s staircase, neither of them truly wanting the other's company until Greg manages to strike up a conversation about her pillow collection. She finds his quirky personality endearing and they make plans to meet on a regular basis.