Hannah attempts to ease Adam into her social circle as Marnie recovers from a second breakup with Charlie and Shoshanna establishes her priorities after her split with Ray. Meanwhile, Jessa is secretly in rehab, but finds herself an unpopular fixture due to her careless attitude with the other patients.

While Marnie gets a place of her own, Adam takes Shoshanna and Hannah on a road trip.

Ray gets used to being a restaurant manager and Marnie takes control of Hannah's 25th birthday party. Meanwhile, Adam gets an unexpected visitor.

Hannah's editor, David, dies, but Hannah's more concerned with what will happen to her e-book. Jessa finds out that a friend from the past faked her own death. Marnie quits her job at Ray's coffee shop.

Caroline is creating tension in the apartment. Hannah finds a new editor, but her previous publisher will not release her book. Marnie asks Ray's opinion of her, but her response is pathetic and desperate, and ultimately proves Ray's point.

Hannah starts a new job doing advertorial work for GQ magazine, but finds it difficult to fit in. Meanwhile, Marnie and Ray make a connection, but soon clash, and Shoshanna takes her relationship with Parker to the next level.

Marnie invites the girls to her mother's friend's beach house for the weekend. While there, Hannah runs into Elijah and the girls learn a lot about themselves through each other.

After conducting an interview with Patti LuPone, Hannah becomes scared that Adam will change due to his being cast in a Broadway play. Meanwhile, Jessa receives an unexpected visit, and Marnie is depressed about her lack of success.

While visiting her ailing grandmother in hospital, Hannah is surprised by a strange request from her mother. Later, she shares an uncomfortable drink with her overachieving med student cousin Rebecca.

Hannah worries about her relationship with Adam, Marnie starts working at an art gallery, and Shoshanna surprises Jasper and Jessa.

Hannah and Elijah have dinner with Patti LuPone, Jessa looks for a new job, and Hannah, Shoshanna and Elijah attend Marnie's open-mic night performance.

The girls each face life-altering news and decisions.