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.

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

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; Adam is shocked by a revelation.

Friends try to help Hannah through a crisis; Hannah and Adam have an honest conversation about their relationship.

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.

With only one class a week, Hannah finds herself doing a lot of nothing in her free time, while a visiting Elijah has become the social butterfly of Iowa. Ray gives Marnie a wake-up call about Desi's true intentions before their meeting with a record label. Shoshanna aces, then blows, a job interview. Adam unwittingly gets drawn into Jessa's chaotic web after an AA meeting. At a poets' party in Iowa, Hannah rants about the undue expectations put on women writers, and takes things too far in critiquing her classmates.

In her first days as a grad student, Hannah discovers she can get more for her money, rent-wise, in Iowa. Later, during a video chat, she slyly prods Marnie for intel about Adam. At her first seminar, Hannah warns her fellow workshop writers that her piece might trigger some intense emotions - but doesn't get the feedback she had hoped for.

After a congratulatory dinner with her parents, Hannah and Adam pack up the last of her 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 she thinks necessary. Jessa is confronted by Beedie's daughter, Rickie, and later seems nonplussed by Hannah's impending departure.