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.

Needing space after a fight with Desi, Marnie goes for a walk and has an unexpected run-in with someone from her past.