On her wedding, Marnie makes sure that everything is perfect, with Shoshanna’s help; while Ray tries to calm a nervous Desi down. Hannah brings Fran as a date, whereupon he has an awkward moment with Adam.
Fran moves in with Hannah, whom her dad turns to for help. Adam runs into Jessa, and they end up spending the day together. Ray is concerned about his business losing customers. Elijah meets a famous TV anchor who comes on to him.
Shoshanna enjoys her new job in Japan, but gets alarmed when she finds out it may soon come to an end. Hannah’s shocked to find on Fran’s phone naked pictures of his exes. Jessa watches Adam’s performance on TV, then discusses it with him.
Hannah and Fran have a spat about work. Marnie rages at Desi for making a big decision without telling her. Elijah and Dill go on their first date. Jessa and Adam sleep together.
Hannah goes with her mother to a retreat that holds surprises for them both. Abigail pays Shoshanna a visit in Tokyo. As Jessa wants to go back to college, she asks her sister for money, but she refuses.
Marnie has a spat with Desi, upon which she goes for a walk and chances on her ex-boyfriend Charlie, with whom she spends the day.
On top of problems at work, Hannah has a fight with Fran. Jessa frets about seeing Hannah at Adam’s play. Elijah has reservations about Dill.
On their trip outside New York, Hannah breaks up with Fran. As Adam finds out that his sister Caroline is gone, he takes care of his niece, with Jessa’s help. Shoshanna is back from Japan. Marnie’s relationship with Desi suffers a setback.
Hannah meets her old nemesis Tally. After a disturbing dream, Marnie tries to work things out with Desi. Shoshanna offers to help Ray with his suffering business.
Hannah’s parents come for a visit, whereupon she decides to participate in a writing event. As Shoshanna’s plan to help Ray pans out, Hermie hires her at the coffee house. After a fight, Jessa admits to Adam that she feels guilty about Hannah.