Shoshanna helps Ray slog through his new oral-history project until a fortuitous encounter with her old boss gives their venture a much-needed boost. Meanwhile, Adam has surprising news for Hannah; and Jessa spends a day off on her own.
Elijah prepares for an open-call audition for a new Broadway show, but is distracted by an unexpected visitor. Meanwhile, a cash-strapped Marnie mulls pawning a family heirloom; and Hannah reconnects with Paul-Louis.
Desi wants to bail on a gig that was planned for a birthday party for Marnie's mom in New Jersey. Meanwhile, Hannah turns down Adam's request to screen his film, but gets important advice from her dad and his new partner, Keith; and Elijah catches the acting bug again after helping a coworker with an audition.
Hannah's mom comes for a visit, but is preoccupied with how to accept the next phase of her life. Meanwhile, Adam and Jessa start shooting their film, but clash over his creative direction; and a grieving Ray can't count on Marnie for support.
Hannah interviews a respected author, who gives her advice on writing and being a woman. Meanwhile, Adam abruptly leaves the set of his latest acting job, so Jessa thinks they should embark on a creative endeavor of their own; Ray is shocked by the sudden death of a regular customer at the coffee shop; and Marnie is confronted with her narcissism.
Hannah goes on a road trip to Poughkeepsie, N.Y., with Marnie and Desi; Andrew accompanies Shoshanna to a networking event for young professionals, where she has an awkward reunion with some former classmates and reevaluates her post-college friendships.
In the Season 6 premiere, Hannah goes to the Hamptons to write a story about a surf camp for women, where she hits it off with the laid-back instructor. Meanwhile, Marnie's divorce from Desi opens a door for Ray, who bristles at her intention to close it when it suits her.