Lovelace and Clarissa arrive at Mrs. Sinclair’s whorehouse and, now that he is there, Lovelace admits to wavering in his honest purpose. The women of the whorehouse—Polly Horton, Sally Martin, and Dorcas Wykes—welcome Clarissa warmly, although she’s distrustful of them. Lovelace has gone so far as to buy second-hand books so that they will appear to be readers of moral literature. Clarissa finds that she cannot hold Lovelace to his promise of separate lodgings and that she must uncomfortably acquiesce to his story that they are already married.
It is revealed that Polly and Sally had been respectable women before they knew Lovelace, well educated and raised as if for a higher class. They had indulged in “public diversions” and became easy targets for seduction. The two are jealous of Clarissa and discourage Lovelace from behaving honorably. Lovelace tells Clarissa he has found a house for her and is in negotiations to buy it from a widow named Fretchville, which provides an excuse to put off marriage. Lovelace throws a party and invites his crew of rakes—Belford, Mowbray, Belton, and Tourville, as well as a woman named Miss Partington. Lovelace gives them all instructions to act respectably, but Clarissa finds them vulgar and offensive nonetheless.
Mrs. Howe writes to Clarissa to forbid her correspondence with Anna. Clarissa agrees, but Anna insists that they carry on in secret with the help of Hickman. Lovelace exults that it is his machinations, through Leman and Uncle Antony, that have turned Mrs. Howe against Clarissa and removed that means of escape.
Lovelace’s friends send him a letter condemning his plan to ruin Clarissa, whom even they can see is a superior being. Lovelace agrees with their praise of Clarissa but mocks their sermonizing: he has resolved to resume his scheming.
Lovelace is at a crossroads in this section, as he wavers between his affections for Clarissa and his inherent libertine ways. Clarissa’s consistent virtue seems about to win him over, and when her father’s curse sends Clarissa into grief and illness, Lovelace is worried and compassionate. He characterizes his proposal as a way of keeping her on earth, which indicates that this despair might have killed her without it. However, it also suggests that Lovelace’s promises (and, essentially, his wicked schemes) are keeping Clarissa away from heaven. After this incident Lovelace resolves to be honest, but he is never fully committed to it, as he continues to build on his contrivances, just in case he changes his mind. Although he believes that marriage is the right thing to do, Lovelace acknowledges that his inability to desist from his libertine intrigues will most likely lead to grief for both him and Clarissa.
Lovelace’s resolution to be an honest man is quickly tested upon arrival at Mrs. Sinclair’s house. The women there goad him away from his albeit shaky resolution and their teasing has a strong effect on him. The women cannot bear all of the blame, however: as soon as he steps into Mrs. Sinclair’s house, the battle seems to have been almost won by wickedness. The house brings out the worst in Lovelace and reinforces his already evil nature: he describes a battle with his heart, which is unusual in that the heart does not represent Lovelace’s better or more caring self, but instead embodies his villainous habits and responds to wicked temptations. Indeed, if it is the women who tempt Lovelace to evil, he has himself to blame for it, since he ruined them in the first place. In a sense, then, Lovelace has brought himself and Clarissa to a place where his own wickedness is concentrated and will entrap them both.