Hannah has one last dinner in New York with her parents and Adam before packing up to leave for the Iowa Writers' Workshop. Meanwhile, Marnie and Desi play a jazz-brunch gig for a tough crowd at a downtown restaurant; Shoshanna's annoyed by her parents after getting her diploma; and Jessa clashes with Beedie's daughter over her caretaker status.

Hannah moves into a new place and is thrilled with the amount of space she can afford, but struggles with life as a grad student when her fellow workshop writers don't give her the feedback she expected.

Hannah has a lot of free time but nothing to do with only one class a week, while Elijah makes his mark on the Iowa social scene. Back in New York City, Ray warns Marnie about Desi's intentions before they meet with a record label; Shoshanna has a job interview; and Adam gets mixed up in Jessa's world after an AA meeting.

Hannah is confronted by her classmates after leaving a non-apology apology letter in their cubbies. After being rejected at yet another job interview, a frustrated Shoshanna spends a day with Ray. Creative and romantic tensions between Marnie and Desi reach a breaking point.

Hannah's friends attempt to help her get through a crisis in her life. Hannah and Adam have an honest conversation together.

Hannah goes for drinks with Fran, a new coworker, before attending an unusual art show. Later, she spends some time alone with Mimi-Rose, while Adam is unnerved by Mimi-Rose's friend, Ace. Meanwhile, Shoshanna helps Ray with his community board election campaign.

Hannah spends an afternoon with a new friend. Marnie and Desi argue over money. Jessa gives Shoshanna advice. Loreen and Tad have a tense dinner party with their friends.

Hannah's maturity is called into question after she is confronted with a family dilemma. Jessa, Ace, Mimi-Rose and Adam have an awkward encounter. Marnie makes an announcement at Ray's campaign party.

Hannah, Adam and Jessa try to convince Caroline and Laird to forgo their planned home birth; Shoshanna is presented with a unique job opportunity; Ray tells Desi what he really thinks about him.