(Written from the perspective of Skeeter.) Sweltering in the July heat, Skeeter continues her work and her relationship with Stuart. She is a bit perturbed when Stuart invites her to go on vacation and stay in the same hotel room as him (unthinkable, since they are not married or even engaged). Though he pressures her, she ultimately refuses. They spend some time together at Skeeter's house, and she asks him the question that has been haunting her: what happened to end his relationship with his ex-girlfriend Patricia? Skeeter wants to know this before she meets Stuart's parents. Stuart refuses to give an answer, saying only that Skeeter would never do what Patricia did. He suddenly gets up and leaves Skeeter's house.
The next day, Pascagoula draws Skeeter aside and tells her that Yule May (who is Pascagoula's cousin) is planning on being interviewed for the book on maids. Skeeter is excited but anxious - she is afraid of what she will learn about the personal life of Hilly Holbrook, who is still her best friend despite their disagreements.
Soon after this, Skeeter receives an unexpected letter from Yule May, who explains that she has been imprisoned for stealing one of Hilly's rings to pay for her twin sons' college tuition. The letter is addressed from the Mississippi State Penitentiary. Skeeter is horrified; she remembers the ring, an ugly, nearly worthless garnet that Hilly never wore. Skeeter learns from Pascagoula that Hilly used her social connections to ensure that Yule May was sentenced to eight times the usual amount of time for petty theft.
Skeeter goes to Aibileen's house, where many prominent members of the Jackson colored community are gathered; she asks what she can do to help Yule May and her family. Aibileen tells her that Yule May had asked Hilly for a small loan of seventy-five dollars to send her boys to college, but Hilly had harshly refused. Now the colored churches are pooling funds to send the two boys to college. Eleven maids come up to Skeeter and tell her that they will help her with the interview project. Skeeter is thankful that this is happening, but heartbroken that it has taken a good woman's imprisonment to make it happen.
During Skeeter's next meeting with Hilly, she can nearly contain her fury at Hilly's version of events; Hilly asserts that black maids often steal family heirlooms so they can sell them to buy liquor pints.
Skeeter and Aibileen start interviewing the maids - eleven have agreed to be a part of the project. She hears stories of tenderness: one maid is concerned about what will happen if she dies before her employer, because the woman is so dependent on her. She also hears stories of horror: one maid's cousin-in-law had her tongue cut out for talking about the KKK. They discuss low pay and hard hours, but also the closeness they feel to some of their charges. Skeeter assures all of them that their names will be kept completely confidential; she also offers each as much money as she can, using earnings from her Miss Myrna column and the allowance her mother gives her. One maid named Gretchen tells Skeeter that she's just trying to make a dollar off black women's stories, and all the maids secretly hate her. Aibileen tells her to leave. Skeeter's next interview is much calmer: a maid named Callie tells her that her employer wrote her a thank-you letter for all the work Callie had done over the years, which Callie appreciated deeply.
(Written from the perspective of Skeeter.) Stuart’s parents warmly receive Skeeter and her family; Stuart himself is still driving back from a business trip. The two sets of parents make conversation; Skeeter's mother mentions that she has heard that the Whitworth's home (a historical landmark) is the centerpiece of historic tours. The Whitworths uneasily admit that Patricia van Deveder's mother is head of the historical council, so they do not take part in historical tours anymore. The group tours the Whitworth home, which is filled with relics of the antebellum- and Confederate-era south, until Stuart returns. The group settles down for dinner. Mr. Whitworth brings up the Life magazine feature on Carl Roberts, a black man who was lynched for saying negative thing about the white Mississippi governor. Skeeter's father says he's ashamed of the violence meted out against black men in the south. Mr. Whitworth says he might agree with the negative things that Carl Roberts said about the governor. Stuart continues to brood over the prior mention of Patricia van Devender.
Mr. Whitworth, extremely drunk, pulls Skeeter aside and asks her if his son is doing all right; he was deeply hurt when Patricia van Devender left him. Skeeter realizes she isn't sure how Stuart really is doing and wonders what she really means to him. She confronts Stuart about what exactly happened between him and Patricia. He confesses that she slept with a Yankee civil rights activist, and that he would not take her back because doing so could jeopardize his father's run for political office. Skeeter asks if he is still in love with Patricia, and Stuart is quiet for a moment before telling her that they should quit things for a while.
(Written from the perspective of Skeeter.) Skeeter hides her breakup with Stuart from her parents and focuses on typing up the maid interviews. She notices that her mother seems more and more frail: she has grown thinner, she eats little, and she vomits frequently.
Skeeter completes the compilation of interviews, and with Aibileen's help, sends them to Elaine Stein. Skeeter does not know if the book will be published but for the sake of the maids, she hopes that it will be.
After a League meeting, Hilly corners Skeeter and asks her why she has ignored Hilly's instructions to advertise the Home Help Sanitation Initiative in the League newsletter. They argue about the "negro activist materials" (Jim Crow Laws) that Hilly took from Skeeter's bag. Skeeter threatens to report Hilly to the League president, and Hilly says it's no wonder that Stuart left her. Skeeter storms out of the room, and begins to hatch a plan....
If any reader liked Hilly before, they certainly do not anymore. Out of pure spite, Hilly used her connections to make sure that Yule May was imprisoned for years without a fair trial, leaving her family adrift. The ring itself was worthless and Hilly didn't event like it; she mainly likes bulling other people. Hilly seems almost Dickensian in her wickedness.
However, Hilly's cruelty backfires. After the imprisonment of Yule May, an educated and admired member of the black community, the maids of Jackson realize that they have little to lose by discussing their experiences. Skeeter herself is stunned at the cruelty of her former best friend: she knows how little Hilly cared about the ring, and she is even more disgusted at Hilly's refusal to give Yule May a small loan to send her sons to college. Hilly's cruelty toward Yule May marks the end of her relationship with Skeeter as well as a surge of interest in the book about the maids.
Stuart's interactions with Skeeter in chapter 19 are suspicious. He invites her to stay with him overnight in a hotel room (alluding to the possibility of sexual activity), but he does not want to tell her about a major event in his life, the cause of his broken engagement with Patricia. This suggests as sort of shallowness in their relationship: he likes her enough to want to sleep with her, but not enough to tell his secrets to her. His reservation ultimately leads to their breakup.
Gretchen's fierce outburst at Skeeter in Chapter 19 is startling. However, it's true that Skeeter is the one who stands to advance her career most through the publication of this book. She may become a famous writer, but the maids will still be maids (though they may be forty dollars wealthier). Gretchen may be acting out of completely legitimate distrust and anger. By associating opposition to Skeeter's work with such an unlikable character, Kathryn Stockett may be attempting to deflect the criticisms of those who allege that The Help makes the stories of black maids secondary to a white woman's ambition.
Chapter 21 expounds upon the theme of the writer's life. Skeeter has put an enormous amount of time and energy into the book about the maids: she has hatched the idea, gained the trust of the maids, conducted interviews with them, typed these interviews, and worked long nights to edit the volume. Despite all of this effort, there is still no guarantee that the manuscript will reach the publishers in time for them to review it, let alone be selected for publication. The writer's life is an enormous amount of effort with very little promise of return.