Shoshanna tries to balance her time at college between sex and studying, while Marnie must accept she and Charlie are through. Also, Adam and Hannah and host a dinner party.

Hannah, Shoshanna and Adam take a road trip; Marnie moves into her own place; Hannah seeks inspiration to meet her editor's deadline.

Adam's eccentric sister arrives unannounced; Marnie becomes controlling over Hannah's 25th birthday party; Ray settles into his new role as manager at the new restaurant.

Hannah tries to process an untimely passing; Jessica tracks down an old friend; Marnie discovers a video that Charlie posted online.

Hannah attends the funeral of her editor; Hannah tries to help Adam and Caroline work through their issues; Jessa makes some positive changes; Ray gives Marnie advice.

Hannah writes advertorials for GQ magazine, but feels stifled in a corporate environment. Meanwhile, Shoshanna wonders if she did the right thing by breaking up with Ray, who has a contentious lunch with Marnie.

Hannah runs into Elijah on a weekend getaway at a Long Island beach house and invites him and his friends over, but she isn't sure how it will affect Marnie's schedule for getting her affairs back in order.

During a GQ advertorial interview, Patti LuPone warns Hannah that Adam's new career path may cause unexpected problems. Meanwhile, Jessa's boredom at work is interrupted by a surprise visit from an old acquaintance. Later, Hannah is assigned to review the Gramercy Park Hotel, and the group celebrates good news with Adam's new friend Desi, whom Marnie finds particularly captivating.

Hannah gets a strange request from her mother while visiting her grandmother in the hospital; Hannah has a drink with her cousin.

Hannah worries about her relationship with Adam; Marnie starts working at an art gallery; Shoshanna surprises Jessa.

Hannah and Elijah have dinner with Patti LuPone; Jessa looks for a job; Hannah, Shoshanna and Elijah attend Marnie's performance.

Hannah receives some news; Marnie divulges a secret to Shoshanna; Jessa's boss asks her for a favor.