After a congratulatory dinner with her parents, Hannah and Adam pack up the last of Hannah's boxes and discuss "the plan" for their soon-to-be long-distance relationship. Marnie and Desi perform as part of a jazz brunch for a distracted crowd at a downtown restaurant. Shoshanna signs for her diploma with her parents, who make a bigger deal out of the event than Shoshanna thinks necessary. Jessa is confronted by Beedie's daughter Rickie, and later seems nonplussed by Hannah's impending departure.

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.

Some soul-searching leads Hannah to an epiphany. Meanwhile, another disastrous interview for Shoshanna ends in a positive; Ray attempts to solve his neighborhood noise issue at a community board meeting; Marnie and Desi disagree on how to define their sound; and Adam is shocked by a revelation.

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 young friend; Marnie and Desi fight over money; Jessa gives Shoshanna advice on the art of seduction; Loreen and Tad have a tense dinner party with their friends Avi and Shanaz.

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 each try to convince Caroline and Laird to forgo their planned home birth. Shoshanna faces a crucial decision when presented with a unique job opportunity. After Marnie and Desi's meeting with a record label exec, Ray lets Desi know what he really thinks of him.