In the Season 2 premiere, Hannah throws a party with her new roommate, Elijah, and is ready to move on in her romantic life despite still tending to a needy Adam and his broken leg. Meanwhile, Shoshanna does her best to avoid Ray; Marnie gets bad news from her boss; and Jessa returns from her honeymoon with Thomas-John.
Hannah's unnerved by Adam's creepy dirges that he posted on the Web, but is miffed by Sandy's critique of her essay. Meanwhile, Marnie considers a new career path; Elijah confesses a recent transgression to George; and Jessa gets a gift from her husband.
Hannah tackles a freelance assignment with some help from a junkie, who lives downstairs, and Elijah, who lets slip a secret in a moment of peak indulgence. Meanwhile, Marnie has an encounter with artist Booth Jonathan at her new workplace and at his studio.
Hannah's grown-up dinner party is marred by her guests' childish behavior, including Marnie's showdown with Audrey. Meanwhile, Shoshanna realizes her relationship with Ray has advanced to a new phase; and Jessa meets Thomas-John's parents.
Hannah gets an e-book deal that comes with a fast-approaching deadline; Marnie hosts Booth's art party; Adam persuades Ray to take a trip to Staten Island; Jessa's depression forces a retreat to Hannah's place.
A visit from Hannah's parents forces her to mask her worries about her book; Marnie is surprised by Charlie's entrepreneurial initiative; a woman Adam meets in AA encourages him to go on a date with her daughter; 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; 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.