As Anne struggles with her geometry homework one night while Marilla is away, she breaks her concentration to have a discussion with Matthew. One of the many questions she asks is if Matthew ever went courting. Matthew responds that he does not think he ever did. Anne tells Matthew it might prove to be a very interesting thing to do. According to her school friend, Ruby Gillis, courting is fun. Ruby has told Anne that when she is old enough to date, she is going to have as many boyfriends as she can gather. Ruby is going to make sure all the boys are “crazy” about her, too. After pondering this, Anne concludes that having a lot of boyfriends might prove too much trouble. She thinks she might prefer having just one, provided he is “in his right mind.” Anne then tells Matthew that Ruby has more experience than she does when it comes to understanding boys and dating because Ruby has many older sisters from whom she has learned. So maybe Ruby has the right idea.

The thought of courting leads Anne to think of her teacher, Mr. Phillips. Rumor has it that Mr. Phillips goes to Prissy Andrews’s house every night to help her study for her entrance exams into college. However, there is another student, Miranda Sloane, who is also preparing to go to college. Mr. Phillips does not go to Miranda’s house, though Anne believes Miranda needs extra help a lot more than Prissy Andrews does. After this reflection, Anne admits to Matthew that there are a lot of things in the world she does not understand.

As Anne continues to force herself through her geometry problems, she hears footsteps outside. She goes to the door and finds Diana standing there. Diana looks frightened. Diana quickly tells Anne that her little sister, Minnie May, is very sick with the croup. Diana has been babysitting while her parents are away, and her sister is coughing terribly.

Upon hearing this, Matthew prepares to go for the doctor and Anne rushes to join Diana as they run toward Diana’s house. Diana is crying by the time they arrive, but Anne tells her not to worry. Anne has quite a few years’ experience taking care of young children. She consoles Diana by telling her that she knows exactly what to do with croup.

By the time Matthew and the doctor arrive, Anne has stabilized Minnie May. Later, when talking with Diana’s parents, the doctor commends Anne for her bravery and knowledge in caring for Minnie May. He tells them that Anne is responsible for saving Minie May’s life.

The next day, Diana’s mother comes to see Anne, but Anne is still asleep from having been up most of the previous night. Mrs. Barry tells Marilla that she is terrible sorry for having been so harsh with Anne and she hopes Anne will forgive her. Because of her heroic efforts to save Minnie May’s life, Mrs. Barry gives Anne permission to resume her friendship with Diana.