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.
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.
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.