Shoshanna and Ray are having sex when she stops it and they fight. She tells him it's his lack of ambition that bothers her, so Ray tells his boss he wants to go back to school, but then he's offered a managerial position at the coffeehouse. When he tells Shoshanna about this, he expects her to be thrilled, but they fight again and end up breaking up. Shoshanna tells him he is negative about everything and Ray leaves angrily and Shoshanna is left in tears.
Charlie is performing oral sex on Marnie when she asks him to tell her how many women he'd been with when they weren't together. Marnie and him eat brunch together and she puts herself out there and assumes they're back together. When Charlie hesitates, she rushes out and they end up confessing their feelings for one another and get back together. By the end of the episode, they seem happy.
Adam and Nat are having sex and are still together after last week's episode. Nat stops him from calling her a "dirty whore" and takes charge of the pace of their sex. She enjoys the sex, but it's clear Adam wants to do things his way.
Hannah is in rough shape throughout this episode because of her OCD; she's behind on her pages for her editor, she hasn't left her apartment, and she refuses to see Marnie. She calls her dad for help, but her father provides her little solace. Hannah cuts her hair off and leaves a voice mail for Jessa to beg for help. She ends up calling Adam, who rushes over to her aid. In the end, he picks her up and they kiss.