Hannah throws a housewarming party with brand-new roommate Elijah, but it’s hard to move on when she’s still playing nurse to Adam. Marnie gets bad news at work and a visit from her mom; Shoshanna avoids Ray at the party; and sun-kissed Jessa returns from her honeymoon.
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.
On a freelance writing assignment to get out of her comfort zone, Hannah befriends the junkie downstairs and parties hard with Elijah, who reveals an explosive secret. Meanwhile, Marnie has a long awaited run-in with artist Booth Jonathan.
Hannah concentrates on preparing to host her first dinner party and Marnie confronts her ex-boss, Audrey. Meanwhile, Jessa meets her new in-laws and Shoshanna takes her relationship with Ray to the next phase.
Hannah tries to hide mounting anxiety about her book from her visiting parents (Becky Ann Baker and Peter Scolari). Marnie is stunned to learn that Charlie has started a successful app company; at AA, Adam meets a boisterous woman (Carol Kane) who coaxes him into dating her daughter, Natalia (Shiri Appleby); and Ray’s aversion to college parties gives Shoshanna pause.
Hannah's deadline worries and pressure from her publisher weigh heavily on her mind; Adam and his new girlfriend have a misunderstanding; Shoshanna avoids Ray at Charlie's work party; Marnie makes a move toward her future.
In the Season 2 finale, Hannah attempts to write her book in one day so her publisher doesn't sue her. Meanwhile, Ray tries to impress Shoshanna with a bold career move; and Marnie gets the wrong idea about Charlie.