A magazine publisher sends Hannah to a surf camp in the Hamptons to write about it after her article on Jessa and Adam's relationship is published in The New York Times. Marnie is still struggling to overcome her divorce from Desi, especially after she sees Ray with Shoshanna.
Marnie and Desi invite Hannah to join them on a trip to Poughkeepsie to provide Ray with a cover story, and she hesitantly agrees. Things take an unexpected turn when Jessa invites herself to a networking event hosted by two of Shosh's former college mates who have recently launched their clothing brand.
When Hannah pays a visit to Chuck Palmer, a famous, award-winning writer who has summoned her after she published an article against him, Hannah discovers who he really is after a lengthy and heated dispute between the two.
As Adam leaves work on a film production, he and Jessa decide to collaborate on a film based on their relationship with Hannah, who conducts an interview with writer Ode Montgomery. Marnie rejects going out with Ray.
After she learns about her daughter Hannah's pregnancy, Loreen seems pleased with the news, but it becomes clear that she has developed a cannabis addiction. Adam and Jessa start filming their movie. As Ray is sick of Marnie's behavior, he informs her that he wishes to end their relationship.
Marnie tells Hannah that she has to tell her father about her pregnancy, after which she faces a difficulty in persuading Desi to play at a club for her mother's birthday. Elijah discovers his dramatic aptitude when he volunteers to perform lines from a play that a coworker is auditioning for.
Elijah resolves to attend a workshop audition for a theatrical version of the 1992 sports comedy White Men Can't Jump. Marnie seeks to sell a family treasure. Paul-Louis calls Hannah again, and she informs him of her pregnancy.
Adam asks Hannah if he may assist her in raising the child. Ray and Shoshanna had lunch with Abigail, a friend and former boss of Shosh. As Jessa decides to take a day off, she has an affair with a stranger in a bar.
When Hannah is offered a job outside New York, Elijah attempts to persuade her to stay, but she's more concerned with finding a better environment to raise her kid. Hannah goes to Shosh's apartment for advise on her relocation, only to discover the other ladies there celebrating Shosh's engagement.
Hannah is surprised when Marnie asks if she may move in with her and help raise her kid. Five months later, Hannah has given birth to a baby boy, whom she names Grover. As she struggles with parenting, Marnie eventually contacts Loreen for assistance, which angers Hannah.