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.
During their first night aboard, Ruby's mind is consumed by sex, while Billy probes for personal details she's reluctant to give up. Comforted by the fact that her husband believes she's on a weeklong yoga retreat – and determined to make Billy jealous – Ruby brazenly connects with Derek, a stranger on the train. Meanwhile, Billy works to shake a persistent figure from his past.
On a regular Tuesday morning, Ruby Richardson is shaken out of her humdrum suburban life when she receives an urgent text that prompts her to fly to New York and board a cross-country train, where she reunites with college ex Billy Johnson. As their adventure begins, Ruby and Billy fight the tension that still exists between them while attempting to root out each other's secrets.