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.
Even Hannah is surprised when she's attracted to a fortysomething doctor and his life of unspectacular stability.
Marnie is asked to act as hostess for an art party thrown by Booth Jonathan and Hannah signs a publishing contract for e-books. Meanwhile, Adam manages to convince Ray to join him on an adventure.
Hannah goes along with Jessa to visit her estranged father, his alternative girlfriend and her teen son in Upstate New York.
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.
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.