Hannah tries to start fresh by dating a new guy and throwing a housewarming party with brand new roommate Elijah. Marnie gets some bad news at work and a visit from her mother, while Shoshanna avoids Ray at the party, and a sun-kissed Jessa returns from her honeymoon.

Hannah gets some unsolicited musical attention from heartbroken Adam & some displeasing opinions on her writing from her new guy. Marnie makes a career compromise when her curatorial dreams are crushed, and Jessa revels in married life while Shoshanna & Ray make magic.

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 hosts a grown-up dinner party to celebrate her writing gig but her friends' behaviour doesn't live up to the setting. Marnie & Audrey square off, while Shoshanna realises she has entered a new phase with Ray. Meanwhile, Jessa meets Thomas-John's parents.

Hannah goes to apologize to an angry neighbour and is surprised by how drawn she is to both him - a good-looking 42-year-old doctor - and the trappings of his conventionally successful adult life.

Hannah signs an e-book deal with a dauntingly tight deadline while Marnie plays hostess for Booth Jonathan's art party. Adam coaxes Ray to go on a Staten Island adventure and a depressed Jessa crashes with Hannah.

Hannah goes along with Jessa to visit her estranged father, his alternative girlfriend and her teen son in Upstate New York.

A visit from her parents forces Hannah to mask her worries about her book, and Marnie is surprised by Charlie's entrepreneurial initiative. A woman Adam meets in AA encourages him to date her daughter, while Shoshanna is irked by Ray's aversion to college parties.

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, and Marnie makes a move towards her future.

Shoshanna and Ray's relationship quickly deteriorates, while Marnie and Charlie reunite following a heated brunch. Hannah faces a lawsuit if she does not finish her book and leaves Jessa an angry message. She and Adam reconnect.