Anna responds to Clarissa's letter and insinuates that Clarissa is perhaps in love with Mr. Lovelace. She warns Clarissa not to move too hastily in this regard or to give the man any cause to encourage his pursuit of her. Anna is wary of Lovelace's character.

In her letter to Anna, Clarissa is at first shocked by her friend's need for such a warning about Lovelace. However, upon rereading Anna's letter, Clarissa decides to reflect on a deeper level of her feelings, wondering if Anna may be seeing something that Clarissa is not aware of.

Afterward, Clarissa concludes that she definitely is not in love and insists that Lovelace is not now and never will be "THE" man. Clarissa writes that she has "great objections" to him, and contrary to what Anna has suggested, her heart does not "throb" for Lovelace.

In Anna's next letter, Anna accepts Clarissa's statement about not being in love with Mr. Lovelace. However, Anna also declares that she will keep an eye on Clarissa and suggests that Clarissa do the same in relation to her feelings.

Anna then reports on an evaluation of Mr. Lovelace provided to her by a Mrs. Fortescue, who has known Mr. Lovelace since he was a child. The first thing Mrs. Fortescue states is that Mr. Lovelace has always been as "mischievous as a monkey." She also claims that Lovelace is a man of pleasure, has a very lively imagination, and is brave and intelligent. He is guilty of neither gambling nor drinking, but nonetheless his character is faulty. He is a very proud man and is not reluctant to boast of his talents and strengths.

Although he is said to be a good writer, Lovelace is secretive about his subject matter. Few people have read anything that he has written, which makes Mrs. Fortescue very suspicious. He also does not seem to be concerned about his reputation, which tends to be unflattering. Mrs. Fortescue does not know if this means he is so arrogant that it does not bother him or that what is said about him is true.

Anna also exposes a rumor she has heard about Clarissa's sister. An underlying emotion that has inflamed Arabella's dislike of Clarissa is that Arabella believes Clarissa has stolen Mr. Lovelace from her. Arabella has confessed to a friend that she is in love with Mr. Lovelace and that Clarissa has stolen him from her.

Because of Arabella's jealousy, she and James have plotted against Clarissa, turning against Lovelace and now insisting that Clarissa marry Mr. Solmes, a man who has promised to bestow generous amounts of money on every member of Clarissa's family if Clarissa marries him.

Adding even more pressure to the situation, Clarissa tells Anna that, hoping to ease the tension in her family, she has handed over to her father the legal administration of her inheritance from her grandfather. She now fears  that if she does not marry Solmes, she may lose that inheritance.