Before heading off to college, an overthinking teenager asks out a former girlfriend in an effort to reconnect and hold on to his past.

Meet Sampson: An introvert who has just graduated high school and spends his last days of summer contemplating his life. No one ever told Sampson Mitchell that going off to college was going to be easy, but that didn't stop them from badgering him on how he should be excited to start a new chapter in his life. With a mind floating back and forth between the present and the past, Sampson tries his best to avoid thinking of his upcoming future. Not wanting to leave full of regret, Sampson decides to form a list of things he should do before college, using his last school newspaper as inspiration. By luck or simply fate, in walks Alexa Newport, an old flame that digs up old feelings that Sampson had for her in the past. Not wanting to let these feeling go, Sampson asks out Alexa in attempt to reconnect with her and to try and maintain a hold on his life. They spend the night talking, reconnecting, and helping each other realize things that they couldn't realize on their own through honesty and compassion.