Mrs. Crupp attempts to intimidate Miss Trotwood as she tried to intimidate Peggotty but David's Aunt Betsey proves too strong a character for her, and David observes that Mrs. Crupp "subsided into her own kitchen, under the impression that my aunt was mad." David is very comfortable in his aunt's care.
Although David loves Dora, he has not told her about his being poor and he decides that he must. At first, she refuses to understand and then she begins to cry. David tries to explain that he deeply loves her, but she tells him, "Don't talk about being poor, and working hard." She is more concerned about whether or not her dog, Jip, will have a daily mutton-chop! David explains that it would help if Dora would try to learn something about housekeeping and cooking, but this causes Dora to become almost hysterical and she faints. Finally, Miss Mills enters the room and calms Dora. Later Miss Mills tells David that Dora "is a favorite child of nature" and that practical responsibilities are beyond her scope.
David discovers that learning shorthand is very difficult, but because he is stimulated by his love for Dora and aided by Traddles' advice and assistance, he becomes rather confident of his skill. Finally, David experiments by trying to record one of the speakers in the Commons. Unfortunately, he discovers that he needs much more practice.
Going to the Commons one day, David is called into the upstairs room of a neighboring coffeehouse by Mr. Spenlow, Dora's father; there, he is confronted by Miss Murdstone, holding all of his letters to Dora. It seems that Dora's dog, Jip, was playing with one of the letters and Miss Murdstone found it. Mr. Spenlow is very angry, and when David states that he and Dora are engaged, Mr. Spenlow is determined to protect his daughter from the "consequences of any foolish step in the way of marriage," even to the extent of threatening to change his will if necessary. Mr. Spenlow says that he will forget the matter if David, in turn, will forget about marrying Dora. When David refuses, Mr. Spenlow gives him a week to reconsider, and if David decides not to, he will send Dora abroad again.
During the week, David consults Miss Mills, but this only makes him feel more miserable and depressed than before.
The next Saturday, David appears at the Commons and learns that Mr. Spenlow died mysteriously the night before. A few days later, Mr. Jorkins, David, and an office clerk search Mr. Spenlow's desk for a will, but none is found; rather, it is discovered that his records are out of order, that he has lived beyond his income, and that Dora will be left with very little money. She is sent to live with two maiden aunts, and the only news David hears of her is by way of a journal kept by Miss Mills, his "sole companion of this period."
Chapter 37 deals foremost with the matter of David's being deeply in love and not quite comprehending what we clearly see: Dora, in her present state, will prove little more than a hindrance to him. He would be far better off with the sisterly Agnes.
The key episode in Chapter 38 parallels Dickens' own love affair with Maria Beadnell. Mr. Spenlow hints that Dora might be shipped off to Paris to prevent her marriage; Mr. Beadnell did that very thing. In the novel, Mr. Spenlow dies, and David is able to marry his sweetheart, but in real life Dickens was not so fortunate to have had this happen.