Hannah gets unsolicited musical attention from heartbroken Adam and displeasing opinions on her writing from Sandy. Elijah questions his sexuality; Marnie makes a career compromise when her curatorial dreams are crushed; Jessa revels in married life; Shoshanna and Ray make magic; and Elijah and Marnie harbor a secret.
Hannah tries to hide mounting anxiety about her book from her visiting parents; Marnie is stunned to learn that Charlie has started a successful app company; while at AA, Adam meets a boisterous woman who coaxes him into dating her daughter, Natalia; and Ray’s aversion to college parties gives Shoshanna pause.
During a GQ advertorial interview, Patti LuPone warns Hannah that Adam's new career path may cause unexpected problems. Meanwhile, Jessa's boredom at work is interrupted by a surprise visit from an old acquaintance. Later, Hannah is assigned to review the Gramercy Park Hotel, and the group celebrates good news with Adam's new friend Desi, whom Marnie finds particularly captivating.
Hannah has one last dinner in New York with her parents and Adam before packing up to leave for the Iowa Writers' Workshop. Meanwhile, Marnie and Desi play a jazz-brunch gig for a tough crowd at a downtown restaurant; Shoshanna's annoyed by her parents after getting her diploma; and Jessa clashes with Beedie's daughter over her caretaker status.
Hannah has a lot of free time but nothing to do with only one class a week, while Elijah makes his mark on the Iowa social scene. Back in New York City, Ray warns Marnie about Desi's intentions before they meet with a record label; Shoshanna has a job interview; and Adam gets mixed up in Jessa's world after an AA meeting.
Thriving at her new job in Japan, Shoshanna flirts with the boss, but reminds her work friends that she has a “kind of” boyfriend back in America. Hannah makes a shocking discovery on Fran’s phone and struggles with how to react. After viewing Adam’s performance on a TV police procedural, Jessa shares her insights into his character.
Hannah and her mom, Loreen, embark on a female-empowerment retreat, where Loreen hopes for clarity in her situation with Tad, and Hannah relishes time away from Fran. In Tokyo, Shoshanna enjoys her budding romance with Yoshi, and gets a surprise visitor from the U.S. Jessa meets up with her sister Minerva and asks for a favor.
Riding a wave of newfound career success, Hannah gets an assignment to write a story about a female surf camp in the Hamptons, where she meets Paul-Louis, an uncomplicated waterski instructor. Hoping to break her old patterns post-divorce, Marnie tells Ray he needs to spend more time at his own place, but Adam and Jessa’s intensity drives him out of the apartment.
Hannah provides cover for Marnie’s secret weekender to Poughkeepsie, which she hopes will help clarify an old chapter in her life. Shoshanna enlists Elijah to be her plus-one at a networking event for young professional women, where Jessa’s antics lead Shosh to reevaluate her post-college friendships.
Hannah interviews influential writer Ode Montgomery, who offers eye-opening advice on being a woman and a writer. When Adam storms off the set of his latest acting job, Jessa suggests they embark on a creative endeavor of their own. Ray considers the course of his life after a regular at the coffee shop dies suddenly. Marnie is confronted with her narcissism.
Marnie tries to convince a resistant Desi to follow through with their planned gig at her mom’s birthday party in New Jersey. After rebuffing Adam’s request to watch his film, Hannah gets advice on an important decision from her dad and his new partner, Keith. Elijah’s thespian talents are rekindled when he helps a coworker run lines for an audition.