After school the next afternoon, Harriet runs straight to Mrs. Plumber's house and watches the maid have a conversation with Little Joe Curry, the delivery boy for the Dei Santi's grocery store. Then she goes to the Dei Santis, which is abuzz with activity. Next stop on her spy route is the Robinsons, a couple who sits in silence and says nothing to each other except when company visits, in which case they show off their house and how "perfect" they are. As Harriet spies, the Robinsons welcome another couple into their house and show them around, and Harriet writes about how she is glad she isn't perfect because she would be bored to death.
Then she goes to Harrison Withers's house, a man who has twenty-six cats and is constantly hiding from the Health Department because he has too many of them. She watches him feed the cats, wondering if he eats the same thing they do. She eventually sees that he has a small tin of yogurt for himself, and then watches him craft birdcages, the work he does that he loves. Before finishing her route, she goes to see Janie. Janie is in conflict with her mother, who wants her to go to dancing school instead of continuing with her science experiments. She tells Harriet that her mother wants her to go to dancing school, too. Janie's mother comes in during their conversation and says the same thing, and Harriet ducks out when one of Janie's experiments explodes with a loud noise and angers her parents.
Harriet announces to her parents at dinner that night that they will never get her to go to dancing school. They calmly try to convince her that it is not so bad, but she continues to refuse and uses foul language, which makes her parents demand that Ole Golly wash her mouth out with soap. Ole Golly comes to talk to her, and manages to convince Harriet that girl spies must go to dancing school, because she has to be able to blend in at parties so that no one will suspect her of being a spy. She begrudgingly goes downstairs to tell her parents she has changed her mind, which causes them to laugh and wonder aloud what they would do without Ole Golly.
Soon it is Thursday, the day that Ole Golly has off to take a night out. Harriet suspects that Ole Golly will go to meet this boyfriend of hers, and decides she will spy on them to figure out who he is and where they will go. Ole Golly tells her her parents are also going out, so she will be alone with the cook. Harriet muses in her notebook for a while about where Ole Golly is going, until five o'clock comes around and she climbs up a tree to watch her leave. Suddenly a man with a black mustache wearing a delivery jacket comes up to the house and rings for Ole Golly. He changes into a nicer jacket and they walk off arm-in-arm. As she continues spying on them, Harriet notices that Ole Golly is not acting like herself, blushing and claiming to like things like going to the movies and eating German food even though Harriet knows she hates both.
When Ole Golly and the man, called Mr. Waldenstein, are out of earshot, Harriet returns to her house and tries to find ways to entertain herself. Before her parents leave for their own night out, Harriet asks her mother how she and her father met. Mrs. Welsch explains that they met on the boat to Europe, when they bumped into each other leaving the dining room and Mr. Welsch threw up because he was seasick. Harriet asks if she knew she was going to marry him then, and Mrs. Welsch says she did not, but she thought he was handsome and constantly thought about him after the funny incident.
Harriet cannot not stay awake until Ole Golly's return, so the next afternoon after school, instead of having her cake and milk, she goes straight to Ole Golly's room to hear about her night. Ole Golly talks cryptically about her evening with little detail, and Harriet writes in her notebook that there is more to love than meets the eye and wonders if she will ever understand it before she is older.
The following Saturday Harriet's parents are going out to a very big party, and are in a fluster preparing for it. Harriet was looking forward to spending time with Ole Golly, but Ole Golly seems to be in a funny mood that day, asking Harriet if she likes asparagus even though she knows perfectly well everything Harriet likes and dislikes. After her parents leave, Harriet is astounded when the doorbell rings and Mr. Waldenstein shows up, dressed in a nice suit and holding flowers. Ole Golly had invited him over for dinner. She introduces him to Harriet, and he tells her that they have a friend in common: Little Joe Curry, because they are both in the delivery business.
Mr. Waldenstein explains to Harriet that once, long ago, he was a jeweler with a very big business and a lot of money. However, he was miserable. He decided he wanted to start over, and asked his wife if she wanted to come with him—however, she did not, so he gave her all his money and she took their son and went away. Mr. Waldenstein became a delivery boy, and immediately enjoyed his life far more. He recently received a promotion to cashier. During this story, Harriet realizes that she likes him.
Mr. Waldenstein suggests that he take the two of them to the cinema. At first Ole Golly refuses, because it would not be right for her to leave the house with Harriet when she is working that night, but Harriet begs to go. Mr. Waldenstein promises that no harm will come to Harriet, and that the evening at the movies would be quiet and enjoyable. Finally she agrees, and Harriet picks out a movie about the Greek gods to see, since she is studying them in school.
To get there, they ride with Mr. Waldenstein on his delivery bike. The only place to fit Harriet is in the delivery basket, which Ole Golly is skeptical about at first, but Harriet is excited to try it. After the movie, they stop by the drugstore so Harriet can have an egg cream. When they return home, however, they realize they have been out later than they thought—it is now midnight, and Harriet's parents are already back, frantically looking for her.
Mrs. Welsch is furious that Ole Golly would take Harriet out without permission, particularly with a man she does not know. Mr. Welsch is a bit more rational, and asks Ole Golly to explain herself. In a frenzy, Mrs. Welsch tells Ole Golly that she is fired, which makes Harriet burst into tears. Ole Golly is astonished, but stands up for herself, saying she hopes they know by now that as long as Harriet is in Ole Golly's care no harm will come to her. Mr. Welsch wants his wife to discuss this reasonably, but instead she marches Harriet upstairs to bed.
Harriet leans over the upstairs banister to eavesdrop the rest of their conversation. Mr. Waldenstein apologizes, but announces that he asked this evening for Ole Golly's hand in marriage, so her departure from the Welsch household would have happened soon anyway. Mrs. Welsch is astounded and about-faces immediately, telling Ole Golly she cannot leave because the family won't be able to manage without her. Ole Golly says that the time has come not only for her, but for Harriet as well, since she is growing to old to have a nurse. While Harriet is shocked, she is also pleased to hear that Ole Golly believes she can take care of herself.
The next afternoon, Ole Golly leaves. First, she explains to Harriet that Mr. Waldenstein asked her to marry him when they were drinking sodas at the drugstore after the movie. She talks about how wonderful it feels to be asked, and Harriet has trouble fathoming the way feelings often do not make sense. She also tells Harriet that they will likely be moving to Montreal, which upsets Harriet because it is so far away. Ole Golly firmly tells Harriet that she does not need her as her nurse anymore. Harriet says goodbye and almost starts to cry, but Ole Golly tells her to stop, because tears will not bring her back and a good spy gets out there and fights through life's struggles. That night, Harriet writes about how she still does all the same things as she did when Ole Golly was here, but she feels like there is an empty hole inside her.
True to her character, Harriet blatantly rejects something that would be considered traditionally feminine: dancing school. In the early 1960s, a time in which gender norms were firmly ingrained in society, most female characters in literature would embrace such an activity. Instead, in Harriet the Spy, both Harriet and her friend Janie turn up their noses at it in favor of activities that are typically considered more masculine, and thus unbecoming for a little girl: spying and conducting science experiments. Fitzhugh's characterization broke stereotypes at a time when they were rarely questioned.
The introduction of Mr. Waldenstein also sends a critical message about wealth, prosperity, and different ways of living. Mr. Waldenstein had a successful business and a lavish lifestyle, but these things do not always equate to happiness. He only found true happiness when he turned his back on materialism and embraced a simpler life, working to earn as much as he needed to live and nothing more. Now, he derives happiness from the people in his life, a fact made clear by his deep love and devotion to Ole Golly. Meeting Mr. Waldenstein and learning his story is an important lesson for Harriet, a girl who lives a comfortably wealthy life and may not think about these things.
Harriet the Spy is a bildungsroman, or a coming-of-age novel, that chronicles Harriet's growth and maturity over time. Ole Golly's departure is the first clear marker of Harriet's coming of age. She has lost her childhood nurse, and is now forced to grow up, because she does not have Ole Golly to look after her. At first, Harriet is proud that Ole Golly believes she is now old enough to care for herself and excited by the challenge. However, she will soon realize that living without Ole Golly will be more difficult than anticipated, and she must be ready to take on that responsibility.
However, the loss of Ole Golly is more than just the loss of a nurse, who physically cares for and watches over Harriet. It is also the loss of a mentor and friend, who gives Harriet advice and teaches her many things, even when she does not realize she is learning. Harriet must not only learn to take care of herself, but also how to exist in the world without Ole Golly's guidance. She must control her temper, think before acting, and reason through problems rationally and maturely. This will be a struggle for an impulsive girl like Harriet, and she has not truly grown up until she learns how to do this.
But Harriet is also growing up in other ways, as she encounters things, like feelings, that are not wholly "rational." Harriet is an extraordinarily rational, systematic person, and her fascination with spying and knowing all things there are to know illustrate how determined she is to find explanations for everything. Some things, however, do not have explanations. This is what she begins to see in these chapters as she watches Ole Golly fall in love. Over and over, Harriet writes in her notebook that she believes she will never understand love. Coming to terms with the truth that there are feelings and ideas that may never make sense is part of growing up, and Harriet has begun this process.