Back in New York two weeks after Palm Springs, Poppy replays the kiss in Croatia and realizes she misunderstood Alex for years. Alex had not regretted kissing her; he had regretted doing it when both of them were drunk and unsure, and he had been hurt when Poppy acted as if it meant nothing. That realization deepens Poppy’s guilt and grief, while Alex’s silence and her uncertainty about her own future leave her emotionally stuck.

At work, Swapna notices that Poppy is withdrawn and unfocused and asks her to take a walk. Poppy privately admits that everything feels difficult: her heartbreak over Alex, her fear of a life in Linfield, her exhaustion with the career she worked hard to build, and her inability to imagine a clear next step. Swapna frames the problem as possible professional burnout and gently encourages Poppy to speak with someone, giving her the card for a psychologist.

Poppy texts Rachel and soon begins therapy with Rachel’s mother, Dr. Sandra Krohn. Although Poppy says she wants help deciding what comes next, Dr. Krohn pushes her to begin with the past instead, and Poppy finds herself talking freely about her family, school, and earlier experiences. Rachel urges Poppy not to run from the discomfort, so Poppy stays in therapy, keeps working at R&R, starts journaling, and experiments with small attempts to build a fuller life in her apartment while also searching job listings in both New York and near Linfield.

On her way to meet Rachel at the end of September, Poppy gets trapped in a subway-door mishap and unexpectedly runs into Jason Stanley, the boy she once liked and who later bullied her in middle school. Jason recognizes her, gets off the train to speak to her, and apologizes. He explains that his cruelty came from his own fear and insecurity, not from anything wrong with Poppy, and he tells her he has admired the life she built. His unexpected kindness destabilizes Poppy because it forces her to confront how long she has defined herself against Linfield and against the wounded version of herself she tried to escape.

After Jason leaves, Poppy understands that she has spent years treating success, travel, and distance as proof that she was not broken. Meeting him in New York shows her that leaving home did not erase her past, and that other people did not stay frozen in the roles she assigned them. By the time she reaches the wine bar, she is crying but newly clearheaded: she tells Rachel that she is going to quit her job, not impulsively, but because she finally sees that her unhappiness is tied to living a life built out of fear rather than genuine desire.