Hailey and Jay used to be best friends, but haven't seen each other in 7 years. A chance encounter at a coffee shop one morning in Chicago forces them to address many old wounds, memories and feelings that had been left unsaid along the way. Will they be able to find their way back to each other? Upstead!

Hailey and Jay get off to a rocky start as partners in 2017, but quickly find out that they enjoy each other's company after all- so much so that they want to spend every NYE together, no matter what. They start an annual New Year's Eve tradition, which follows them throughout different stages of their partnership, friendship, and relationship along the way.