This chapter details Rosie and Penn’s first date. Rosie is in the first year of her medical residency at UW Hospital. Penn is enrolled in a creative writing MFA program. They have both agreed to a blind date; Penn agreed for writing material and Rosie agreed because Penn sounded nice over the phone. Penn feels nervous before meeting Rosie, then instantly realizes she is the woman he will marry when he meets her. Over dinner, Rosie expresses sympathy when Penn reveals he is an only child. Penn is puzzled. Rosie tells Penn about Poppy’s death. “Is that why you think only-childhood is so sad?” Penn asks Rosie (14). Rosie confirms. “Maybe that’s why I like you already,” Rosie tells Penn. “We’re both only children” (14). When Penn gets home after the date, he knows his daughter’s name will be Poppy.

After Rosie and Penn first meet, Rosie tells Penn that she is too busy to date due to her grueling residency schedule. Penn responds that he wasn’t aware that having a boyfriend “took up brainspace” (15). However, Penn uses Rosie’s reluctance to be romantically involved as an opportunity to woo her. He spends all his time writing and reading in the waiting room of the hospital where Rosie works. He begins to prefer working and studying at the hospital, writing stories about the people who come in and out. One night after her shift, Rosie finally takes Penn home with her. Rosie reflects that Penn’s stints writing at the hospital vetted him for being a good father, willing to wake up at all hours of the night to appease a crying baby. Though she’d been planning to return to her native Arizona, Rosie stays in Madison due to the prestige of the program and later because of the birth of her sons.

While Rosie is delivering their fifth child, Poppy, Penn is at home with their four boys telling them a bedtime story. He begins telling them a story he told Rosie on the first night they spent together, about the misadventures of a reluctant prince named Grumwald. When the boys complain about the story’s meandering plot, Penn explains, “Stories are very mysterious. That’s their other point. To tell themselves. And to be mysterious” (29).

Poppy, who is assigned male at birth and named Claude, speaks her first word, “bologna,” at nine months old, though no doctor believes Rosie. Rosie and Penn assume this has something to do with Poppy’s brother Rigel having regularly demanded bologna to eat when Poppy was a baby. But Poppy was advanced in other ways too: She crawled at six months, walked at nine months, and at three years old wrote and illustrated a mystery series about a crime-fighting panda and puppy. Poppy claims that she will be many things when she grows up: a chef, a cat, a train, a farmer, an ice-cream cone. She also says that she will be a girl. She asks her mother if she will be able to wear a dress to work when she grows up, and Rosie says yes without giving the question much thought. One Thanksgiving, Poppy writes and directs a play that she and her brothers perform. She wears a princess dress in the play, and she continues to wear it throughout the holiday break. When school begins, she refuses to take the dress off for school. The only way that Rosie can coax Poppy out of the dress is by insisting that real ladies “do not wear rumpled, dirty dresses […] they wear clean, pressed ones” (36).

Though the children are getting older, Penn continues to tell them about Grumwald’s adventures. Responding to Poppy’s request for a girl in the plot, Penn introduces a new character, Princess Stephanie. Rosie’s mother, Carmelo, who lives in Phoenix, visits Madison for the summer. Carmelo lets Poppy try on her dresses, jewelry, and shoes. Poppy asks Carmelo if she will love her even if she wears dresses. “I will love you even if you wear a dress made out of puppies,” Carmelo replies (43). Carmelo buys Poppy a pink bikini, which she wears to the community pool. Other children and their parents look at him strangely. Ben, Poppy’s studious older brother, admits to Penn that he is worried Poppy will be made fun of in school.

Carmelo gives Poppy a purse, which she uses as a “lunch tote” (53). Rosie is called in to speak with Poppy’s kindergarten teacher, Becky Appleton, who scolds Rosie for allowing Poppy to bring a peanut butter sandwich to school in her lunch tote due to the potential peanut allergies of other students. Rosie counters that she had read the school manual cover-to-cover and never saw anything about peanut restrictions. Becky replies that it is not an official rule, but instead, “It’s about good faith and respect. Doing unto others. The Golden Rule” (51). Becky then suggests to Rosie that Poppy not bring a purse to school, claiming it is a distraction to the other children. Poppy begins wearing dresses at home, taking off her school clothes and changing into the dresses immediately after school. Rosie and Penn become concerned about the effort Poppy is making to hide who she is.

Poppy dresses up as Grumwald for Halloween, complete with a cardboard cut-out that indicates the story’s “ceaseless narrative” (61). Rosie notes how long it has been since she has seen Poppy looking like a little boy. At the school parade, the principal, Dwight Harmon, expresses concern for Poppy to Penn. Dwight notes that Poppy is quiet and does not have many friends, which he feels is unusual for a five-year-old. Dwight encourages Penn to let him know if Poppy needs anything.