Trey MacDougal

In the show, Trey MacDougal (Kyle MacLachlan) is a doctor from an upper-class family with an overbearing, frequently present mother who views Charlotte as a rival for her son's affections. Trey and Charlotte meet after Charlotte has resolved to meet her husband in the coming year. Their initial introduction is one in which he proves her knight in shining armor: having had a horrible date, Charlotte is nearly hit by his taxi. Trey gets out of the taxi to help her, and it is implied that they fell in "love at first sight." Charlotte feels that Trey is an ideal boyfriend/husband-candidate. After only a mere month of dating, Charlotte becomes anxious to receive his proposal. When introduced to the royal MacDougal matriarch, Bunny, Charlotte sees how easily Trey can be manipulated and cannot help noticing his mother's methods. Frustrated with waiting, Charlotte uses Bunny's technique and suggests (at a restaurant) that they should marry, to which Trey casually and characteristically responds, "All righty". Charlotte is furious at this response, because it was hardly the proposal of her dreams—the next day she tells Carrie she proposed to herself. Later, Trey makes up for it by stopping in front of Tiffany & Co. during a walk and suggesting that they look for "the most beautiful engagement ring they have."

Within the show, they decide not to have sex until they are married, but on the day before their wedding, Charlotte gets drunk and visits Trey's apartment to seduce him. Trey is unable to perform, possibly meaning he is infertile. Charlotte addresses her concern to Carrie before she walks down the aisle, but Carrie attempts to comfort her and the marriage takes place. After they are married, Trey continues to be unable to perform in the bedroom. It is implied that his problem is not impotency, as Charlotte catches him masturbating in the bathroom to pornographic magazines. Because of their sexual problems, the two separate. They later get back together when Trey agrees to address the problem, and though he initially has problems, they eventually are able to have regular sex. After some time, Charlotte finds she has not been able to get pregnant, and discovers that she has some fertility problems. The couple starts trying IVF, but Trey, after initially agreeing to it, ultimately decides that he does not feel ready for children. The two divorce because of their different goals in the marriage.

Harry Goldenblatt

In the show, Harry Goldenblatt (Evan Handler) is Charlotte's divorce lawyer. Although Charlotte is initially put off by Harry's constant sweating, messy eating, shortness, baldness, and hairy body, she ends up sleeping with him when Harry confesses his intense attraction to her. She finds it is the best sex she has ever had. She tries to keep their relationship strictly sexual but soon becomes emotionally attached due to Harry's kindness, cleverness, and obvious love for her. Initially she tries to change him so that he will more closely fit her image of the ideal man, but these attempts cause Harry distress and Charlotte realizes their futility, and gradually accepts Harry for who he is. Charlotte converts to Judaism in response to Harry's avowal that he can only marry a Jewish woman, but she soon ends up ruining the relationship in a fit of anger by demanding he set a wedding date and telling him that everyone wonders why a catch like her is bothering with a schlub like him. Hurt at hearing what he believes to be what Charlotte really thinks about him, Harry breaks up with her. But after several weeks of bad blind dates, Charlotte bumps into Harry at the local synagogue singles' night and admits her wrongs, professing her deep love for him and agreeing finally to accept him as he is, rather than molding him to suit her. She says that she does not care if he ever marries her, as long as she can be with him. Harry is touched and proposes to Charlotte on the spot.