Mr. Big, referred to by Carrie and her friends simply as "Big", both excites and eludes Carrie throughout the run of the show, as she always believes he is the man for her, but many times, he's not able to fulfill her emotional needs. A wealthy financier (Samantha calls him "the next Donald Trump" in the pilot), who is based on New York publisher, Ron Galotti. Carrie and Big's on again, off again relationship begins and ends in season one and then a second time in season two. After two years of commitment issues and emotional unavailibility, Mr. Big marries a twenty-something socialite Ralph Lauren executive named Natasha (Bridget Moynahan). Within seven months of his marriage he begins to pine after Carrie and starts to have an affair with her, until Carrie breaks it off. After divorcing Natasha, Big and Carrie become friends, with their sexual history always lying just beneath the surface. He eventually moves to the Napa Valley in California, but is visited once by Carrie, while on her book tour and he returns to New York a year after that for an angioplasty. In the end of the series, he returns to tell Carrie he is ready to commit to her, but is brutally rebuffed. He doesn't give up, and, after the blessing of Charlotte, Samantha and Miranda, tries to re-claim her love one last time in Paris. In the end, the two prepare for an open, honest relationship in New York.

Aidan Shaw is Carrie's other long-term boyfriend. He is a sweet, good natured furniture designer and Mr. Big's emotional opposite. At first, Carrie is put-off by their seemingly perfect relationship and over time works through her issues of emotional unavailability, but ultimately, she cannot meet his needs and they break up for good. In season three, Aidan ends "it" when she comes clean about the affair, they get back together a year later, eventually move in together and she accepts his marriage proposal before the break up for the second and final time. Aidan eventually marries and has a child.

Jack Berger was Carrie's intellectual counterpart, a sardonic humorist writer whose career is cooling down just as Carrie's is heating up. Theirs was a relationship of witty banter and common thoughts, but everything falls apart when his defeated attitude clashes with her contented state. Carrie learns, when it comes to relationships, Berger's talk is just that; after they agree to try and make things work, he breaks up with her through a post-it note.

Aleksandr Petrovsky is a famous Russian artist who becomes Carrie's lover in season six. He sweeps her off her feet with huge romantic gestures and shows her the foreign pockets of New York that she has never seen before. Her relationship with him brings up all sorts of questions in Carrie's mind about finding love past "a certain age" and whether or not she wants children. When he's preparing to return to Paris for a solo exhibit he invites Carrie to come live with him, which she does, after several deliberations (and one fight) with her friends. After spending some time there, she realizes that he will never reciprocate the level of emotional involvement that she offers because his life and career will always come first.

Trey MacDougal fits Charlotte's knight in shining armor archetype to a tee; a Scottish American heart surgeon from family money, their whirlwind engagement and a fairy tale wedding stop cold with a sexless honeymoon, brought on by Trey's impotence. After a brief separation, they reunite with a healthy sex life only to discover that Charlotte will have difficulty getting pregnant. Eventually, their disagreements on whether or not to pursue in vitro fertilization lead to divorce.

Harry Goldenblatt is Charlotte's divorce lawyer who is incredibly attracted to her from the beginning. She is not attracted to him, but tries to pursue a sex-only relationship with him, which leads to one of exclusivity and love. After her conversion to Judaism and one big argument that sends them in separate directions for a few weeks, the two marry and begin trying to have/adopt a child. In the end, they are approved for a Chinese adoption.

Skipper Johnson is a geeky, sensitive twenty-something web designer whom Carrie introduces to Miranda. From the moment they meet, Skipper is enamored with her, but Miranda is unimpressed and irritated by him. They date for a short time, before Miranda breaks up with him due to "being in different places".

Steve Brady is a bartender who has an unconventional on-again, off-again relationship with Miranda. Having been stood up by Carrie, she meets him unexpectedly at the bar at which he works, what she thinks is a one night stand but turns into dating. Their differences in income, aspirations and status, as well as their attitudes about living together and having kids are the catalysts for their break ups. Over the course of the show, Miranda puts Steve through the wringer quite a bit, but he looks beneath her cynical exterior and finds her softer side, while at the same time, choosing his battles carefully. In season four, he opens his own bar, called Scout (alongside Aidan) and gets Miranda pregnant (despite losing a testicle to cancer and Miranda having only one functioning ovary). They decide to raise the child (Brady Hobbes) together, separately, but are back together towards the end of Season Six, they have a small intimate wedding ceremony and he convinces her to move to a house in Brooklyn.

Robert Leeds is a sports medicine doctor who moves into her building during season six. He is the seemingly perfect man: successful, sexy, and utterly devoted to her. Robert and Miranda have lots of fun and great chemistry, but when the time comes, she is unable to declare her love for him.

James is a man Samantha meets while out by herself at a jazz club, she makes a conscious effort to not sleep with him until she gets to know him first. When they finally do have sex, she discovers that he is under-endowed to the point that she cannot enjoy herself. She begins pulling away physically and cannot bring herself to tell him--until she is faced with the prospect of couples counseling.

Maria Diego Raez is a sensual lesbian artist that Samantha meets at a solo exhibit while admiring her work. Maria is immediately attracted to her, but since Samantha doesn't believe in relationships they try to maintain a friendship, the chemistry proves to be too strong and it isn't too long before Samantha is introducing her lesbian lover to her stunned friends. At first, Samantha has a great time "getting an education" as Maria teaches her about lesbian sex and how to make an emotional connection while making love. Unfortunately, Samantha begins to grow uncomfortable when the relationship talk starts to replace the sexual activity and Maria is equally uncomfortable with Samantha's sexual history. The two separate, after they have sex with a strap-on.

Richard Wright is a successful hotel magnate who doesn't believe in monogamy until he meets Samantha. He seduces her, and when their no-strings-attached sexual relationship begins to escalate, both parties struggle to keep their emotional distance. Eventually, they give in and attempt exclusivity, but, being a stranger to monogamy, Samantha is plagued by suspicion at every turn. When she does catch him cheating, she breaks up with him, but eventually takes him back after he begs for her forgiveness. In the end, Samantha still has her doubts about Richard, and breaks up with him. Towards the end of the series, Richard re-surfaces, admitting that Samantha was the best thing that ever happened to him.

Smith Jerrod is a young waiter Samantha seduces in a trendy restaurant. She tries to maintain her usual sex-only relationship with him, but he slowly pushes for something more. He is a wannabe actor whose career Samantha jump starts using her PR connections, getting him a modelling job that turns into a film role. Just when she thinks Smith's age and experiences aren't enough for her, he gives her unconditional support during her fight with breast cancer. In the final episode, Smith tells her that he loves her, which she counters with "You mean more to me than any man I've ever known", which, for Samantha is a far greater statement.