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

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.

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'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.

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 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 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 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 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.