2020
S01E16 finale
Ruby is living a humdrum existence when one day she gets a text inviting her to fulfill a youthful pact, promising true love and self-reinvention, by stepping out of her life to take a journey with her oldest flame.
Ruby and Billy decide to spend a day in Chicago before making any rash decisions about their next moves. As the two anxiously await check-in at a lavish hotel, Ruby meets an exciting woman at a department store, while Billy tries to handle a relentless Fiona. Later, Billy comes clean about what drove him to run.