Christie invites a man named Jeremy to be her date at Marnie’s husband’s 40th birthday party. Because he also sees Dr. Rosen for therapy, she is more relaxed and open with him than she usually is with men. During the party, she takes him upstairs to look at Marnie’s baby’s clothes, and he is uncomfortable. On the way home, he says he’s a loner and works a less-than-impressive job. Christie doesn’t like this, but she is excited when he asks her on a second date.

Christie and Jeremy are able to be vulnerable with each other on the second date. He rests his hand on hers throughout the film and they go back to his house for tea. He asks to kiss her, and she allows herself to really experience it and open up to him.

Dr. Rosen reminds Christie that she has to share everything that happens with Jeremy in both groups (and Jeremy does too). Christie doesn’t love this but does it anyway.

Her third date with Jeremy ends with his invitation for Christie to spend the night; however, Jeremy asks that they just kiss and sleep—that’s all he’s ready for. The next morning, he says he might play a computer game all day. At her first group, people applaud his honesty and kindly imply that his reticence is understandable. At Christie’s new group, they mostly see these behaviors as red flags. Dr. Rosen tells Christie that the situation mirrors her personal conflict.

Jeremy and Christie keep dating and slowly escalating their physical intimacy. Christie tries to convince Dr. Rosen to tell Jeremy to speed up. Dr. Rosen prompts Christie to reveal that she is currently wearing three bras: She hates her breasts and even sleeps in a bra. He prescribes a henna tattoo that says “I hate my breasts” received in Jeremy’s company.

Jeremy and Christie go to the henna artist. While waiting for him, Christie remembers talking to the women in her second group about hating their breasts: They all have negative experiences with their own. Christie also remembers wearing a strapless, sweetheart-neck gown to junior prom. She and a big group of other couples stopped on the way there to drink. She remembers being surrounded by all the boys in the group and laughing with them as the buzz set in. One by one, they each put two fingers between her breasts and continue laughing, as does she. The first boy then puts his whole hand into her cleavage. She steps away but keeps laughing, as she begins to experience shame.

After getting the tattoo, she is able to put on a T-shirt and take her bra off to sleep in Jeremy’s bed. That night, they share a truly intimate moment of admitting “I don’t know what I’m doing” (127) to each other.

One evening after spending the day studying, Christie decides that she will have a magical walk down Michigan Avenue with Jeremy and then sleep with him. Instead, he makes a beeline for California Pizza Kitchen and afterward wants to go to bed. This makes Christie so angry that she takes some dishes to the fire escape and smashes them with a hammer.

In the first group the next day, Dr. Rosen connects the incident to purging and tells her to buy eye protection and invite Jeremy to do it with her. In the second group, Christie loudly and violently expresses frustration. The other members want Dr. Rosen to do more for her, but he is silent.

Christie admits that until then, “All [she’d] ever done with anger was swallow it or throw it up” (133). Christie’s expression of anger at Dr. Rosen ends with her pulling her hair out and Nan comforting her. She still feels stuck.

Dr. Rosen helps Christie ask Jeremy to spend time outside the house with her and to spend five minutes kissing her. He finally sleeps with her, but the physical intimacy is still moving too slowly for Christie. Jeremy asks Christie to buy him sneakers and a subscription to a magazine on Dr. Rosen’s advice. Christie feels exploited but listens when Dr. Rosen shows her that it might meet her relationship needs too. When Dr. Rosen advises Jeremy against making a particular month “oral sex for Christie month,” Christie yells at him in both groups and accuses him of prioritizing Jeremy’s needs over hers. Marnie points out that Christie is allowing this to happen.

Thanks to a large advance, Christie takes Jeremy on a trip to Italy. He is uninterested in planning the trip and spends a lot of it studying for the LSAT, leaving Christie to do bike tours and other activities alone. She calls Dr. Rosen from a pay phone and expresses her loneliness. She returns to the hotel and lies down next to Jeremy in bed. He masturbates and refuses her invitations to help.

Back in Chicago, Jeremy’s life deteriorates, and Christie tries to fight his depression. She works impossible hours and uses her salary to buy Jeremy groceries and a new comforter. One night, desperate for intimacy, she insists on giving Jeremy oral sex he doesn’t really want: He hasn’t showered in days. In her second group meeting later that week, she voices an epiphany: “I don’t want to suck a dirty dick” (146). Dr. Rosen tells her she doesn’t have to, and she decides to stop showing up at Jeremy’s and trying to save him from depression and alcohol addiction.

Christie meets an attractive intern at work and starts flirting with him. He kisses her one night and emails her the next day. Christie asks her groups if she should go further—there’s not a lot of long-term potential here. Both groups encourage her. The first time she sleeps with "the Intern,” it is clear that he wants her. She has an orgasm and then cries. Both groups are proud of her, especially Dr. Rosen. The Intern sleeps with her five times and then dumps her because he is Jewish and she is not, even though she promises to convert. Dr. Rosen draws a connection between himself and the Intern to help Christie see the trust they have built with each other and its potential to be used as a springboard for other relationships. Christie owns her progress and vulnerability but longs for a deeper connection. On a phone call, Dr. Rosen promises a new assignment to help with this.

There is a new member in the morning group—Reed, an attractive middle-aged man seeking therapy after cheating on his wife. Christie is attracted to him and spends the whole session picking threads out of a dishcloth as she faces her heartbreak over the Intern. At the end of the session, she asks for Dr. Rosen’s help. He invites her to drop the all-women group and start attending a biweekly group. Christie feels shame at the thought of needing so much therapy but ultimately decides to do whatever will help.