Phoebe feels nervous and excited for the first Book Buddies session with Finn’s fourth grade class. Before Finn arrives with the older kids, two of Phoebe’s preschoolers, Ava and Max, pretend to be pregnant, which leads to a dramatic meltdown when another child “diagnoses” Ava’s pretend baby as a boy, contradicting her plans for a girl. Phoebe skillfully de-escalates the situation just as Finn’s class arrives. Later, a student named Danny asks a series of personal questions, including whether Finn plans to get Phoebe pregnant. While Phoebe is mortified, Finn handles the questions with impressive calm. He tells Phoebe he admires her teaching so much he has adopted a “What would Phoebe say?” (100) mindset with his own students. Seeing their rapport, Phoebe’s colleague Cheryl deliberately brings up Jeffery’s trivia night in front of Finn, prompting to invite him. Finn eagerly accepts, saying he’ll bring his roommate and calling the outing a date, which sends Phoebe into an internal panic.

Phoebe discusses her anxiety about Finn and the upcoming trivia night with her therapist. She reveals her laminated checklist of tasks to help her lose her virginity—a reworking of Sandy’s original assignment to list her personal accomplishments. While Sandy worries Phoebe is putting too much pressure on herself, she encourages her to take control of the situation at trivia night. At the bar, Phoebe nervously awaits Finn’s arrival while her friends try to calm her down. Jonathan, acts unusually withdrawn and expresses his disapproval of Finn, making Phoebe suspect he might be jealous.

Finn arrives with his roommate, Noah, and the group dynamics become tense as Jonathan deliberately separates himself from Phoebe and Finn. Phoebe attempts to check an item off her list by complimenting a stranger’s shoes, but it backfires when she realizes his foot is in a cast. Later, Noah mentions his upcoming birthday party to Meg, and Finn turns to Phoebe to invite her as well. He puts his phone number into her phone, noticing she has received many texts from Matthew. Phoebe feels overwhelmed by the sudden influx of romantic possibilities with Finn, Matthew, and a potentially jealous Jonathan, realizing her focus has shifted from when she would find someone to who it might be.

Phoebe has an anxiety dream. She’s at the altar with Teacher Rob when both Jonathan and Finn burst in and object, demanding she choose between them. As she freezes in panic, a notification comes in on her phone from the word game she plays with Matthew: “Matthew Baxter has played OBJECT for fifteen points” (119). Phoebe wakes up on her flight to New York en route to Jamie’s wedding.

That morning and the previous morning, she had tracked Jonathan’s location on Find My Friends, both times finding him at the same address on Sweetzer Avenue in Sydney’s neighborhood. Overwhelmed by her romantic prospects, she decides to “pick a lane” and focus solely on Finn. She texts Matthew with a vague excuse for canceling her trip, apologizing that she won’t be in Rochester after all.

When she lands in New York, she tries to check off an item on her list—“Find the cutest guy on the plane to help me with my luggage” (135)—by asking an attractive man named Bryan to help with her bag. Bryan agrees, but dislocates his shoulder in the attempt, and she flees in embarrassment. Her sister Jamie picks her up, and at her childhood home, Phoebe feels lonely and sad. To combat her feelings of inadequacy after seeing her high school yearbook, she creates a new list with 19 of her personal accomplishments, resolving to add a 20th during the wedding weekend.

At the rehearsal dinner, Phoebe puts the final touches on the event she planned. The evening is disrupted when Aunt Carol, whom Jamie had proactively seated at a table far away from Jamie and Ethan due to her tendency to behave inappropriately, moves her chair to the family table. Aunt Carol complains that Jamie sat her at the wrong table and dismisses Phoebe’s single status by insisting she’s a lesbian. Provoked, Phoebe spontaneously announces she “sort of [has] something happening with a guy back in LA” (141). Her family eagerly questions her about Finn, but Phoebe realizes she knows almost nothing about him. Aunt Carol doubles down, suggesting Phoebe’s anxiety is just a cover for her sexuality, Phoebe finally confronts her. She firmly states that her anxiety is a real and valid reason for her lack of dating experience and that she is proud of her progress in managing it. Defeated, Aunt Carol retreats to her original table, and Phoebe counts the successful confrontation as her 20th personal accomplishment.

On the day of the wedding, Phoebe practices her maid-of-honor speech. She feels a pang of sadness to see Jamie wearing their mother’s veil, which she had always imagined wearing first. A brief but firm dispute ensues when her mother demands Phoebe cover her octopus tattoo for photos. When Jodi threatens to have the photographer edit it out, Phoebe runs to intercept him.

Stunned, Phoebe realizes that the photographer is Matthew, who is hurt and confused to see her, realizing that Phoebe lied about canceling her trip. The discovery creates a tense and awkward family photo session, where the chemistry between Phoebe and Matthew become obvious to her family. Phoebe promises to explain everything to him later.

After her sister’s wedding ceremony, Phoebe avoids Matthew. Fueled by tequila, she calls her therapist, Sandy, who advises her to tell Matthew the truth about her dating anxiety. At the reception, Phoebe’s aunt tries to set her up with a waitress, Dee, who expresses interest in Matthew. A surge of jealousy motivates Phoebe to get drunk enough to finally confront him. She confesses that her severe anxiety caused her to panic, and she apologizes for lying. Matthew is understanding, reassuring her that he likes her and wishes she had been honest. Emboldened, Phoebe pulls him into a janitor’s closet to kiss him, but he gently rejects her twice, stating he doesn’t want their first kiss to happen while she’s drunk. Humiliated, she exits the closet and breaks out in stress hives.

Phoebe’s father comforts her as she confesses her anxiety, her fears about being a 30-year-old virgin, and her romantic failures. Her father reveals that he has similar anxieties, which calms her. During her Maid of Honor speech, Phoebe falters until she hears an encouraging cheer from Matthew in the back of the room. She sets down the paper and delivers the rest from memory without a hitch.