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.
Hannah gets a new freelance gig, and her editor suggests that she should try cocaine for the first time to write about her experience. In the process, she gets to know her downstairs neighbor, Laird. Meanwhile, Marnie meets her old artist flame, Booth Jonathan, who takes her home to show her his studio.
Elijah moves out, and Hannah invites a group including Charlie, Audrey and Marney to dinner. Jessa meets Thomas-John's parents, which finally prompts a confrontation between husband and wife. Shoshanna discovers that Ray may be living with her.
A man comes to the coffee shop to complain to Ray that someone is leaving trash in his trash cans. Hannah follows him to his brownstone to confess and ends up spending the rest of the day, and the next day, with him.
Hannah is hired to write an e-book, but has trouble finding inspiration. Booth asks Marnie to host a party with him for a gallery opening. Ray goes to see Adam, and they end up traveling to Staten Island to return a stolen dog.
Hannah tries to hide mounting anxiety about her book from her visiting parents. Meanwhile, Marnie is stunned by news that Charlie has started a successful app company; Adam gets set up on a date; and Ray's misanthropy gives Shoshanna pause.
Pressure from Hannah's aggressive publisher (John Cameron Mitchell) and a looming deadline further jeopardize Hannah's mental state. Adam and his new girlfriend have their first misunderstanding. Marnie makes an awkward step in following her dreams.
Season Two Finale. In order to avoid being sued by her publisher, Hannah must write her book in a single day. Marnie misinterprets Charlie's intentions; Ray makes a career move which he hopes will impress Shoshanna.