Season 5

Marnie attempts to organize her upstate wedding to Desi. Shoshanna has to try and carry out out Marnie's wishes. Fran is involved in an awkward moment with Adam.

An erratic roommate causes Fran to move in with Hannah. Hannah receives an urgent call from her father.

Thriving at her new job in Japan, Shoshanna finds herself flirting with her 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 Fran disagree about their respective teaching methods. Marnie fumes over Desi's decision to launch a major construction project in their studio. Jessa pushes Hannah away over an awkward rice-pudding meetup. Elijah gets closer with Dill Harcourt. 

Hannah and her mom embark on a female-empowerment retreat, where Loreen hopes for clarity on her situation with Tad, and Hannah relishes some 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.

Needing space after a fight with Desi, Marnie goes for a walk and has an unexpected run-in with someone from her past.

Hannah gets reprimanded by the school's principal, and her response tactic infuriates Fran. At Adam's play, a nervous Jessa worries about seeing Hannah after their fight, and Marnie shares some news with Ray. Elijah attends a swanky party at Dill's apartment, where he gets the impression that he might be one of many.

Stranded after her summer road trip with Fran is cut short, Hannah is rescued by Ray, but their trip back to NYC gets derailed. When he hasn't heard from Caroline, Adam stops by Laird's place and stays to help with the baby. Back from Japan, Shoshanna gets a wakeup call over a sushi lunch. While recording a new song, Marnie is given parameters for her relationship with Desi.

After Hannah gives Principal Toby some unexpected news, she runs into her old friend-slash-nemesis Tally. Marnie has an unsettling dream and later tries to work things out with Desi. Noticing business is suffering at Ray's, Shoshanna offers to help with marketing, performing some clandestine research on their competition. Elijah makes his pitch to Dill that their relationship should be exclusive.

Elijah and Loreen help Hannah with her plan to participate in The Moth Story Slam. Marnie prepares to go on tour with Desi. Shoshanna's plan for an "anti-hipster" Ray's takes off. After helping take care of the baby, Jessa and Adam have an epic fight.