HBO's 1998 smash hit Sex And The City is perhaps best remembered for its discussions of sex and dating so frank they make even today's viewers blush. But the comedy-drama series equally owes its continued relevance to a cast of (mostly) loveable and relatably flawed characters. These 30-and-40-somethings navigate romantic and professional hurdles and triumphs in Manhattan's elite circles of the late '90s and early aughts.
Of protagonist Carrie Bradshaw and her best friends Miranda, Samantha, and Charlotte, each viewer will, notoriously, have their own favorite. But some of the men the foursome comes into contact with - boyfriends, husbands, and undecideds - prove just as divisive to fans. Ultimately, some characters' foibles absolutely outweigh their virtues, while others are clearly worth rooting for.
Trey
Charlotte York's first husband, Trey MacDougall, proves to be one of the most irritating characters in a show which sees almost countless outrageous men pass through the heroine's lives. Although initially a quiet charmer to Charlotte, his issues quickly become apparent.
He allows his mother Bunny MacDougall to bulldoze into his and Charlotte's lives and puts up few boundaries to protect the young couple's independence. And one of the show's most excruciating plotlines finds an extremely insecure Trey forcing Charlotte to make every possible concession - and still get nowhere - in dealing with his erectile dysfunction.
Aidan
Aidan Shaw is Carrie's second long-term boyfriend in the show, and functions as a foil to her then-ex Mr. Big. Where Big was detached, cryptic, and noncommittal, Aidan is loving, relaxed, and puts all his cards on the table - or so it seems.
Aidan is Sex And The City's resident 'nice guy.' While outwardly pleasant, he expects Carrie to change her personality, habits, and lifestyle to fit him - a doomed strategy memorably visible in Season 4's cabin fever-ridden trip-to-the-country episode. Although not a terrible boyfriend, Aidan is pushy and makes Carrie irritated, restless, and unfulfilled, none of which make him particularly attractive.
Mr. Big
Mr. Big is the guy that Carrie just can't get out of her head. Unfortunately, he's also emotionally unavailable, he plays games, and he hates being vulnerable. When Carrie begs to be told she's "the one" in the first season finale, he won't even budge, and in the next season, he's reluctant for her to join him at a work placement in Paris. (And that's not counting the hypocrisy of his engagement to Natasha after saying he's done with marriage.)
On the other hand, his electric chemistry with the show's heroine, his wicked sense of humor, and his growth into a genuine friend of Carrie's in later seasons make him a highly flawed but somewhat likable love interest.
Carrie
Carrie is Sex And The City's fast-talking and chain-smoking protagonist typically found pounding the pavement in way-too-expensive clothes, attending high-profile parties as a minor celebrity, and pondering the state of modern relationships in front of her computer.
Though not quite an antihero, Carrie stands out as one of TV's more divisive protagonists in recent memory. Although whip-smart, funny, and bold, she's often self-centered, impulsive, and bad at communicating in relationships. And, ironically considering her profession as a sex columnist, she can be highly judgmental of bisexual boyfriends and sexually adventurous pals alike.
Charlotte
Charlotte York gets a lot of flack for being the most conservative and traditional of Sex And The City's girlfriends. But keen fans will recall that although Charlotte has her moments (like immediately storming out of the friends' favorite café when Samantha brings up an unsavory sexual anecdote), she participates in a variety of discussions and escapades (like dressing in drag) that defy her typical characterization.
Charlotte is loyal and supportive, and although she has apparently rigid ideas of what she wants, she proves admirably flexible and adaptable in getting it.
Smith
Smith Jerrod is an unusual love long-term interest for the high-flying Samantha Jones: a struggling theatre actor who Samantha undertakes to transform into a bonafide star. But he proves to be one of Sex And The City's best and most charming boyfriends.
He's a steadfast supporter to Samantha during her battle with breast cancer and committed, easy-going, and forthcoming throughout their relationship. In one of his most subtly endearing scenes, he finally gets Samantha to hold his hand in public - a huge step for the often flighty PR maven.
Harry
Of Charlotte York's husbands on Sex And The City, Harry Goldenblatt is miles ahead of the competition. Originally her divorce attorney, Harry proves a charming, funny, and lighthearted ally to Charlotte during her difficult separation from Trey and her fight to keep her apartment.
It's heartwarming to see his love for Charlotte grow even as she is uncertain about beginning a new relationship, and aside from taking longer than Charlotte would like to propose, he does little wrong in their (temporary) breakup. He's also receptive to her needs - for one memorable instance, around the notion of a clothing-optional household.
Steve
Steve Brady is just about as charming as the men get on Sex And The City. The Queens-born bartender with the sweet smile wins over the cynical Miranda after they meet at the bar, and the pair begin a passionate romance. Their eventual breakup is due to differences in schedules, lifestyles, and finances, but it doesn't mean the end of Steve's time on the show, as the exes unwittingly conceive after a one night stand.
Steve is a solid partner, supportive co-parent, and caring father, and always wants the best for Miranda - and no fan can forget the adorable second-season scene where Miranda learns he loves nothing more than morning cuddles.
Samantha
PR professional Samantha Jones, Sex And The City's infamous "trysexual," lives life according to her own rules, and fans love her for it. The effervescent beauty can always be relied on for a quip, an invitation to a fabulous event, and a hilarious story of her wild sexual escapades.
Although she's known to run out on her friends when gentlemen call, she is a consistent source of laughs, adventure, and wisdom for those close to her, and she brings a hefty dose of levity to her sometimes neurotic trio of best friends.
Miranda
Miranda Hobbes isn't only Sex And The City's most relatable character; she's also its most loveable. Although her tendencies towards being critical and pessimistic can cause conflict with her friends, she ultimately cares for them fiercely and wants to see them happy and successful.
It isn't flawlessness that makes Miranda so appealing to fans. Rather, it's her vulnerability in the face of struggles - whether an unexpected baby, a stagnant career, or finding a compromise in relationships. Despite her mistakes, the sometimes chilly lawyer always has her heart in the right place.