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Clarissa writes to Solmes, telling him bluntly that she cannot like or esteem him, and accuses him of meanness and a lack of generosity if he continues to pursue her. Solmes writes back to say that her letter has only encouraged him. He is not insulted by being called selfish; he can see no reason why he should do anything just to make someone else happy. James finds out about the letter to Solmes and writes insultingly to Clarissa, telling her he will not open any letters she sends him because her “knack at letter writing” might complicate what should be a simple case of duty.

Lovelace is staying at an inn in a small town near Harlowe Place. The innkeeper has a pretty daughter whom Lovelace nicknames Rosebud. Rosebud’s grandmother beseeched Lovelace to be merciful to Rosebud—that is, not to seduce or rape her. Lovelace appreciates having his power recognized and says that he will spare the girl. He refuses to ruin a poor girl with no support to fall back on once he abandons her, and he is also concerned that his actions might get back to Clarissa. He decides that he will give Rosebud money so that she can get married and says that this good deed will balance out some of his sins.

Lovelace reveals that he is paying a Harlowe servant, Joseph Leman, to spy for him and to manipulate the family. Lovelace plans to sneak into Clarissa’s presence so he can judge her feelings for him. If he finds that he has no hope of her favor, he will simply abduct her: “That would be a rape worthy of Jupiter!”

Lovelace disguises himself and hides behind a woodpile so that he can catch Clarissa retrieving her letters from the hiding place. She is terrified, but he acts very respectfully and she is partially convinced of his good intentions. Anna teases Clarissa for pretending that she is not in love with Lovelace. Clarissa writes back in a series of letters that are continually interrupted by visits from family members and her old nurse, Mrs. Norton, who all try to convince her to marry Solmes. Clarissa evaluates Lovelace’s good and bad traits, finding plenty on each side, and admits that her family’s tyrannical opposition to him has made her like him more. She concludes that “were he now but a moral man, I would prefer him to all the men I ever saw.”

Mrs. Harlowe sends Clarissa an affectionate letter, including a list of the clothes and jewels Clarissa will be given on her marriage. Clarissa is affected by the kind tone of the letter and feels torn between duty and her sense of right. Arabella pays her a visit that becomes a battle of insults. Clarissa accuses Arabella of acting out of disappointed love. It is made clear that Arabella and James have plotted together to deprive Clarissa of her favored position and her grandfather’s estate. Mrs. Harlowe visits Clarissa, along with Aunt Hervey and Arabella. Arabella prevents her mother and aunt from softening toward Clarissa.

Anna writes a humorous letter about her feelings for Hickman and imagines what Hickman, Solmes, and Lovelace must have been like as children. She wonders why the prudent, sober men who would make good husbands cannot be as attractive and appealing as rakes. Lovelace unexpectedly visits Anna and asks her to help him win Clarissa over. Although he assures her of his love and his family’s support, his threats of revenge on the Harlowes convince Anna that he is a violent man, and she counsels Clarissa to claim her estate and become independent instead of marrying either Lovelace or Solmes.