Inspired by Jonathan’s bravery, Phoebe decides she’s finally ready to call Matthew. When he answers, she’s shocked to discover he’s in Los Angeles for work, and they agree to meet immediately. At a bar, Phoebe confesses the truth about her anxiety, her inexperience with dating, and the list she made to challenge herself to lose her virginity. Matthew is understanding and non-judgmental. He makes his own confession: The viral video he sent Phoebe of Bev the octopus solving a Rubik’s Cube, which inspired Phoebe’s tattoo, was created by AI. Phoebe laughs, feeling amused rather than upset.

They spend hours talking and doing crosswords, and their connection deepens. As the bar closes, Matthew asks her on a proper date and promises to fly back to LA for it. He drops Phoebe home but is too nervous to kiss her goodnight. After explaining the situation to a worried Jonathan, Phoebe wakes the next morning to learn Matthew has already booked a flight back to LA for the following weekend.

Jonathan comes out to their friend group, whose reactions are varied. He meets up with Finn but returns defeated, telling Phoebe that Finn is not ready to come out and that they are taking space from each other. The following Monday at work, Finn avoids Phoebe until the end of the day, when he approaches her to apologize. Phoebe reassures him, acknowledging that she had misinterpreted their connection, and they agree to be friends. Later, during her therapy session with Sandy, Phoebe explains her recent epiphany. She realizes that her anxiety doesn’t mean she’s broken and that her belief that it did had caused her to push people away. Having moved past this mental block, Phoebe announces that she is officially ready to start dating.

Phoebe and Meg help Nora with last-minute packing for her move, which is scheduled for the next day. The mood shifts from lighthearted to emotional as Phoebe and Meg express sadness that Nora is leaving. The usually stoic Nora remains composed until Phoebe finds a framed photo of the three of them from a college trip to Disneyland. The picture shows a groggy Nora asleep between Meg and Phoebe on a roller coaster, and the frame is inscribed with the message, “We’ll always be here to hold you up.” (252) The memory and the sentiment cause Nora to finally break down into sobs. She clutches the photo, insisting it needs bubble wrap for protection. Unwilling to be left alone, Nora agrees that all three of them will go to the store together. Meg and Phoebe physically support the distraught Nora as they walk to the car, echoing the memory from the photograph.

After dropping Nora at the airport, Phoebe picks up Matthew for their first official date. In her excitement upon seeing him, she forgets to put her car in park, and Matthew has to jump in to stop it from rolling into traffic. They go to the Santa Monica Pier, where an attempt at a first kiss is interrupted by one of Phoebe’s young students, Danny, who asks Phoebe why she’s there with Matthew instead of Finn. When Matthew asks about it, Phoebe worries that the moment will turn awkward, but Matthew reassures her he’s just jealous of anyone who gets to spend time with her.

Later, a roller coaster ride makes Matthew violently ill. Afterward, while brushing his teeth, he tells Phoebe she could completely lose it in front of him, and he would never think less of her. Deeply moved by his acceptance, Phoebe initiates their first kiss. They return to her apartment and find her friends Jonathan, Alex, and Meg waiting to meet Matthew. After brief introductions, Phoebe and Matthew escape to her bedroom. They reflect on their perfect first date and kiss passionately on her bed.

In their group text conversation, Nora asks for an update on what Phoebe and Matthew are doing. Jonathan, Alex, and Meg report that Phoebe and Matthew went upstairs two hours ago and have not come back down. Listening at the door, they supply Nora with play-by-play updates—“lots of giggling […] possible bed creaking” (269) and a moan they attribute to Phoebe. Nora expresses her excitement and frustration at not being there. The friends describe Matthew as adorable and completely smitten with Phoebe, observing that she feels the same way. Three hours later, Phoebe sends a single smiley face emoji to the group, implying her encounter with Matthew was a happy and successful one.

As Matthew packs to leave after an intensely romantic weekend, a distraught Phoebe convinces him to change his flight and stay until Thursday. While helping him unpack, she discovers a birthday card from him, which he quickly takes back, promising a different gift. Later, Phoebe asks Matthew about his past on the Hinge app, and he reveals he joined it after a bad breakup. The thought of him with his ex-girlfriend, whose name was Anna, makes Phoebe physically ill with jealousy. To distract her, Matthew recounts his perspective from the night of Jamie’s wedding. He confesses that he was feeling dejected after she had canceled on him twice and was thinking about her right before she approached him. He admits that when he first saw her, he was hung up on her. The chapter ends with Matthew suggestively asking Phoebe to put on the dress she wore that night.

On the morning of Phoebe’s 30th birthday, Jonathan surprises Phoebe with a custom bookshelf filled with all her books he secretly rescued from the curb. Matthew’s gift is a personalized crossword puzzle with clues based on their relationship. Touched, Phoebe tells Matthew she wants to be exclusive, saying, “no pressure, but I just want you to know […] I won’t be doing any crosswords with anyone else” (278), and he agrees. Later, Jonathan and Matthew lead Phoebe to a bar under the pretense of a small gathering, but she walks into a large surprise party Jonathan organized with Matthew’s help. Her family, friends, and coworkers are all there, including her family and Finn. During the party, Matthew tells Phoebe it’s okay to introduce him as her boyfriend, which she happily does to everyone. Phoebe and Matthew also witness the obvious romantic sparks between Jonathan and Finn. Reflecting on the past month, Phoebe feels immense gratitude. She acknowledges she is now 30 and still a virgin, but she is no longer in a rush to adhere to an arbitrary timeline.

While visiting her parents for Thanksgiving, Phoebe loses her virginity to Matthew in her childhood bedroom. She asks him if he would ever consider moving to LA for their relationship. He says he is in love with her and has already been researching a move. His confession gives her the confidence to initiate sex. She realizes she is in love with him too and tells him so.

As Phoebe flies home to LA, she finds herself obsessing over their relationship and new sex life, prompting her to research everything from sex addiction to relationship OCD. Her therapist, Sandy, confirms that these kinds of thoughts are a new manifestation of her existing OCD. Inspired, the narrator starts a new project, a checklist for managing her condition. She discovers a newfound sense of self-acceptance, concluding that her brain works differently as her life changes, and that there was never anything wrong with her.