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Every One Of Carrie's Love Interests On Sex And The City, Ranked

At this point, "Sex and the City" has become a franchise that encompasses multiple TV shows, books, and movies — not to mention the original newspaper column of the same name that started it all. But the main anchor point remains the HBO series that originally ran from 1998 to 2004. "Sex and the City" was a groundbreaking series, exploring four adult women's stuggle to balance their personal and professional lives in a far more frank, honest, and positive manner than most other shows had done up to that point.

Carrie Bradshaw (Sarah Jessica Parker), the writer behind the in-universe Sex and the City column, is the main character of the show, and her relationships with men tend to be the focal point of any given episode or arc. While her pursuit of Mr. Big (Chris Noth) is never far from her mind, she does connect (or attempt to connect) with a wide variety of other men over the course of the original series. Which men stand above the rest and which sink to the bottom? We're here to find out. This is every single one of Carrie Bradshaw's love interests on "Sex and The City," ranked from the absolute worst bachelors in Manhattan to the guys worth moving to Paris for.

25. Keith Travers

Though he'd already appeared in several notable movies, when Vince Vaughn showed up on "Sex and the City" in 2000, he still hadn't quite made the leap into being a big-name star. Viewers exclaimed, "Hey, it's that guy!" when he showed up as Keith Travers in Season 3's "Sex and Another City," rather than shouting, "Hey, it's Vince Vaughn!"

Vaughn has never exactly been known for his huge range as an actor, and his performance as Keith is no different — he's a fairly basic Vince Vaughn character. This means he's charming, but his fast-talking California style just isn't really a good fit for the comparatively chill Carrie. But that's not what makes him her worst partner in the show's entire run. No, he earns that dishonor when it's revealed that he completely fabricated his job, as well as his Hollywood clout. No relationship that is built entirely on lies has ever, or will ever, be successful. 

24. Jake

Jake, who shows up in Season 2's "They Shoot Single People, Don't They?," is Bradley Cooper's earliest screen credit: He played this wannabe lover a year before he played Ben in "Wet Hot American Summer." Who is this inaugural character? Jake is a jerk, plain and simple. The only reason he doesn't make the very bottom of this list is that he isn't a liar — or at least, he doesn't seem to be. Jake and Carrie encounter each other when her spirits are low following her disastrous New York Magazine cover story. Rather than use the opportunity to cheer her up and get in her good graces, he piles more misery onto her and takes pleasure in doing so. The spoiled icing on the rotten cake is revealed when he refuses let Carrie out of his car when she demands to leave.

23. Patrick Casey

One of the worst things Carrie ever does is force herself back into Aidan Shaw's life, only to break his heart all over again. We bring it up here because it's something she does multiple times throughout the series, including to Patrick Casey (Richard Joseph Paul) in Season 2's "Was It Good For You?"

Patrick is trying to get sober, and is resistant to getting serious with Carrie while doing so. But she insists ... only to turn around and accuse Patrick of moving too quickly when he more or less replaces his addiction to alcohol with an addiction to her. This isn't her fault, but he probably didn't want her to be his girlfriend to begin with because he knew this was a possibility. That said, when he shows up at her house in the middle of the night — drunk, mean, and screaming personal details about their intimate encounters for all her neighbors to hear — the sin is his and his alone.

22. Howie Halberstein

By Season 6 of "Sex and the City," Harry (Evan Handler) and Charlotte's (Kristin Davis) relationship is in full swing, and Harry is clearly established as one of the best — if not the best — men in the entire "Sex and the City" universe. So Carrie has every reason to think that a friend of Harry's is a safe bet for, at the very least, a weekend of harmless fun. However, her physical encounter with Howie Halberstein (Bryan Callen) in "The Catch" is anything but.

Howie is so bad in bed that he literally causes Carrie physical pain. At this point she decides that there won't be a second encounter, and tells him so in a very polite way. This should be the end of it, but Howie proves he's no more mature than a teenager when he uses his groomsman's speech at Harry and Charlotte's wedding to insult Carrie in front of everybody. Suffice it to say, he probably doesn't go home with anyone that night. 

21. Kurt Harrington

Kurt Harrington (Bill Sage) is notable for being Carrie's very first encounter in the series. In the pilot, Carrie is exploring the concept of women who approach the world of dating the way men do. In her studies, she examines her relationship with Kurt. He ends up showing her a good time, and we're led to believe they engage in a friends-with-benefits thing for a while. But he doesn't really feel like boyfriend material. 

It's obvious that, at least at this point in his life, Kurt isn't looking for anything more than fleeting physical relationships with women. Carrie, try as she might, has ultimately never really been a big fan of this. Kurt exists primarily to put Carrie in the right place at the right time to have her first encounter with the man she comes to call Mr. Big. The rest is "Sex and the City" history. Kurt is important ... but mostly because he establishes someone else.

20. Wade Adams

Wade (Cane Peterson), who pops up in Season 3's "Hot Child in the City," fulfills every stereotype of the guy who works at a comic book store: He's a man-child who still lives with his parents. This might seem like some ridiculously broad character writing, and perhaps it is, but Wade has issues beyond his nerdiness. Mainly, he blames Carrie for the marijuana his parents eventually find them smoking. Moreover, he doesn't hesitate to point the finger when they're confronted — this guy was ready and waiting to lay the blame anywhere but himself. Whether or not he's a silly caricature is up for debate, but he was clearly never going to be a good fit for Carrie.

19. Bradley Meego

Not everyone who ranks relatively low on this list does so because they're a bad person. In fact, there are few faults in Bradley Meego (Patrick Breen), a handsome, charming, well-off doctor with a house in the Hamptons who appears in Season 2's "Twenty-Something Girls vs. Thirty-Something Women." That's a lot of Carrie's dream guy boxes ticked off right there. Sadly, like so many other men Carrie becomes involved with, Bradley has one major thing going against him, and it's the one thing that matters most: He isn't Mr. Big.

This becomes especially obvious when Carrie crosses paths with Big and his new wife, Natasha (Bridget Moynahan). No matter what else is going on in Carrie's life or who she's seeing at the time, any encounter she has with Big completely derails everything. In this case, it instantly makes Bradley a non-factor in her life. What could've been a long, happy, and healthy relationship is over before it even has a chance to truly start.

18. Willy

Carrie has an ugly tendency to use people. One unfortunate example involves Willy (Wallace Langham), whom she goes out with in Season 6's "To Market, to Market" for no other reason than she's feeling nervous about her impending first date with Jack Berger.

Most people in this position would go see a movie, do some shopping, or any number of other things that don't involve roping someone else into their problems. But Carrie opts to distract herself with Willy, and their date collapses into one embarrassing mishap after another. Just about anything that can go wrong does go wrong. Afterwards, Carrie ends up feeling better about the date than she expected, while Willy is left with cringeworthy memories.

17. Gilles

Though she's a dyed-in-the-wool New Yorker, Carrie occasionally has dalliances with out-of-towners. The first major example comes in Season 1's "The Power of Female Sex." Gilles (Ed Fry) has a French accent and smooth European charm to match, and he and Carrie spend several romantic days together. When Carrie wakes up the morning after they finally spend the night together, however, she realizes that Gilles is gone. He left no contact information whatsoever – but he did leave an envelope containing a whole lot of cash.

Apparently, Gilles thinks Carrie is a sex worker. It should be noted that the two were introduced by Carrie's friend, who is a sex worker. It's not a completely unfounded thing for Gilles to assume, then, but it's still one heck of a leap. Either way, she never sees Gilles again.

16. Bill Kelley

Years before he began his time in "Mad Men" and the Marvel Cinematic Universe, John Slattery played politician Bill Kelley on Season 3 of "Sex and the City." Things start well between Bill and Carrie. He seems like a better, more stable, and more emotionally available version of Mr. Big. The sparks fly, and a genuinely interest develops between them.

But Bill eventually reveals a certain kink Carrie isn't willing to participate in. Once she makes her disinterest clear, he turns the tables and reveals a much uglier side of himself. Bill shames Carrie by claiming he can't risk his career by being in a relationship with someone who writes a sex column. This is infuriating, but Carrie gets her revenge by embracing the career he's shamed her for and writing a column about him.

15. John McFadden

Carrie isn't big on entirely physical relationships, but she's not totally averse to them. Take John McFadden (Dean Winters), who pops up in Season 2's "The F*** Buddy." She's had a successful friends-with-benefits thing going on for some time with him. But eventually, she wants more, and decides to try and make a boyfriend out of him.

As it turns out, John is a terrible match for Carrie in all places beyond the bedroom. He lacks anything of substance to contribute to any given conversation, and is generally somewhat dull. Unfortunately, trying and failing to make something more out of this situation means there's no going back to the purely physical relationship they previous shared. Thus ends the arrangement between John and Carrie. 

14. Seth

Rock star Jon Bon Jovi shows up in Season 2's "Games People Play" as Seth, a man Carrie meets in the waiting room at a therapist's office. The irony of the whole thing is that this therapist ends up telling Carrie that she's prone to picking up the wrong men — and Seth is very much the wrong man. Why is he seeing the therapist? He has a tendency to lose interest in women after he has sex with them. Carrie learns this after they do the deed — right after, while they're still lying in bed together. 

Maybe it isn't entirely Seth's fault that he has such an issue. And hey, he's at least doing the work to fix it. But giving Carrie a heads up about it before they sleep together seems like the decent thing to do. At least it helps her have a breakthrough regarding her own issues, so it isn't a total loss. 

13. Sean 2

One of the long-held stereotypes "Sex and the City" helps dispel is the myth that all women just want to meet a man and settle down as fast as possible. In fact, it even takes things a step further by having men who very much are interested in settling down as soon as possible and see every woman they date as a potential wife. In terms of Carrie's relationship history, no guy embodies this more than Sean (Scott Rabinowitz) from Season 1's "Bay of Married Pigs."

There's nothing blatantly wrong with Sean, and the couple of dates he has with Carrie seem to go well enough. But it soon becomes apparent that he's looking to speed things down the marriage track, and Carrie just isn't there yet at this point in her life. Sean is then nudged along to Charlotte, who definitely is on the hunt for a husband. But Charlotte and Sean get into a disagreement over place settings, and that's the end of that.

12. Jeremiah

Jeremiah (Sam Ball) is another guy forced to live in Mr. Big's shadow. Season 2's "The Caste System" reveals that he and Carrie have had a flirtation for years, which finally culminates in spending a night together. But then, Carrie finally gets the call she's been waiting for: Big tells her that he loves her.

Of course, this only being Season 2, it ends up being just another dead end between Carrie and Big. He is, once again, stringing her along without any concrete plans to follow through. So Jeremiah is left behind because of an empty promise, despite all indications that he's a great guy and could've been a really solid partner for Carrie. Hopefully he goes on to a much happier situation with someone who doesn't have an eye on someone else.

11. Sam

Just as he was starting to break through in film in the late '90s, Timothy Olyphant did his "Sex and the City" boyfriend tour of duty in Season 1's "Valley of the Twenty-Something Guys." Sam is a younger man Carrie takes a gamble on, and initially, he gives her all the younger man perks. He's fun, an enthusiastic kisser, and always up to spend a night out partying at a moment's notice.

But younger men aren't without their drawbacks for women a bit further along in life than they are. In Sam's case, that means his absolute garbage pile of an apartment. But the tipping point comes when it's time for Sam to make Carrie some coffee and, discovering he doesn't have coffee filters, decides to use toilet paper instead — and doesn't see what the big deal is in doing so. Sam might've been great for a much younger Carrie, but she's well beyond toilet paper-filtered coffee at this point in her life. 

10. Aleksandr Petrovsky

One of the greatest dancers of the 20th century, Mikhail Baryshnikov only has about a dozen movie and TV acting credits to his name. So it's pretty noteworthy that he had a nine-episode stint on "Sex and the City," playing prominent love interest Aleksandr Petrovsky.

Carrie's main partner through most of Season 6, Petrovsky looks as though he's being primed as the guy she's going to end up with. And perhaps that might've been the case, were he not so prone to putting Carrie second, behind his art career. In his defense, he's pretty frank about who he is and what his priorities are. But that list of priorities is never going to have Carrie at the top of it — which he makes abundantly obvious when he abandons her at the opening of his Parisian show — and she isn't okay with that. 

9. Sean 1

With so many different names to pick from, it seems a little odd that Carrie dates two different Seans over the course of "Sex and the City." This Sean (Eddie Cahill) is the one whose bisexuality becomes a sticking point for Carrie, and ultimately leads to their break-up. 

Carrie tries to be progressive, but a game of spin the bottle proves to be a bit too much for her to handle. She's at least willing to admit it's her own hang-ups that are the issue, rather than Sean himself. And it's good that she removes herself from the relationship early on. But it's clear from moments like this why "And Just Like That" places so much emphasis on the ladies learning about gender and sexual identity.

8. Jack Berger

Jack Berger, who appears in Seasons 5 and 6, leaves a major legacy on "Sex and the City": He's the guy who breaks up with Carrie on a Post-it. This isn't a great look, and it's a big part of the reason he doesn't crack the top five. But he is still in the top 10, because he actually comes fairly close to being the perfect guy for Carrie.

Berger (as he's typically called) is a writer, which gives them a lot to bond over. Of course, this ends up manifesting itself as a negative, once Berger becomes unable to handle Carrie being more successful than him. His inability to take constructive criticism and his still-raw feelings about his ex don't do much to help his case, either. But when things are going well between him and Carrie, he's the source of some of her happiest moments on the show. If he were capable of working through some of his issues, he could have been her dream guy.

7. Joe

Hooking up with one of the New York Yankees is definitely a story someone like Carrie would love to tell. She gets the chance in Season 2's "Take Me Out to the Ball Game," when she finds herself with Yankee rookie Joe (Mark Devine). The two initially seem to be a terrific match and have a great time together, even ending up in the tabloids — something that only increases the cachet of a sex columnist.

But as it so often goes, Carrie's feelings for Mr. Big ruin everything with Joe. When the two are kissing, she literally cries into Joe's mouth. It's hard to move on from a moment like that, so they don't bother trying. Like several other guys on this list, Carrie and Joe really could've gone all nine innings (and then some) had Big not wedged his way into Carrie's thoughts.

6. Ray King

Carrie's stint with Ray King (Craig Bierko) in Season 4's "Defining Moments" and "What's Sex Got to Do with It?" might come the closest to surviving Big's intervention. Carrie and Big are in a place at this point where they're trying to be friends. As such, Big thinks he might be able to tell Carrie how much he dislikes Ray. Shockingly, that alone isn't enough to sink the relationship.

Instead, Carrie and Ray's downfall comes by way of Ray's obsession with jazz music. It's great that he has a passion, but he can't keep his focus on anything but jazz — before long, he's right back to talking about it. This is so problematic, it even manages to eclipse the fantastic physical connection he and Carrie share. Carrie is forced to take her leave, but at least her time with Ray proves that Big can't ruin all of her relationships with other men.

5. Jeremy

Jeremy (David Duchovny) appears in Season 6's "Boy, Interrupted." He and Carrie were high school sweethearts, and the pair has retained nothing but fondness for each other. So many great love stories start with two people who were once together, then find each other again later in life. But in this case, there are other things in play that make a relationship difficult. Specifically, Jeremy is a current resident of a mental health facility. 

Carrie isn't completely thrown by this fact. But starting (or re-starting) a relationship just isn't the best thing for Jeremy to do while trying to get healthy. Plus, the facility is in Connecticut, which means they'd have to embark on a long-distance relationship. Jeremy and Carrie part ways once again in one of the most amicable break-ups in the entire series.

4. Vaughn Wysel

Justin Theroux plays Vaughn Wysel in Season 2's "Shortcomings." A writer who's good-looking enough to have his own spread in GQ and has a family Carrie absolutely adores (and vice versa), he earns a notable place in Carrie's history.

There are two main problems with this relationship. First, Carrie likes Vaughn's colorful family a little more than she likes him. Second, he has some performance issues in bed. This isn't necessarily a deal-breaker — but the fact that he refuses to discuss it with Carrie definitely is. Shutting down rather than talking about one's issues only guarantees that said issues will be ongoing. Without physical intimacy or real honesty, Carrie just doesn't see a future with Vaughn. Saying goodbye to his fabulous mother is the hardest part.

3. Ben

 Season 2's "The Freak Show" is all about the worst types of men women encounter in the dating world. Carrie ends up seeing four different guys within the episode, three of whom prove her point. But the last one ends up showing her that she's capable of being a freak as well.

Carrie's on edge when she meets Ben (Ian Kahn), having just dated three terrible guys. But Ben ends up being more or less perfect. He's so perfect, in fact, that Carrie goes snooping through his things when he leaves her alone in his place, looking for evidence of what she assumes must be his hidden freakiness. But she finds nothing. After busting her in the act, Ben asks her to leave — and Carrie realizes she's the weirdo in this situation.

2. Mr. Big

One of the main undercurrents running throughout all six seasons of "Sex and the City," its two films, and follow-up series "And Just Like That," is Carrie's on-again-off-again love affair with Mr. Big (Chris Noth). For much of the original show, he toys with her, strings her along, and keeps her just close enough so that she stays on the hook, but never gets reeled in. At one point, he marries another woman entirely ... and has an affair with Carrie.

In spite of all of this, Carrie and Big finally end up together, and their marriage — which doesn't occur until the first film — is pretty perfect. Viewers might occasionally hate Big and yell at Carrie when she allows herself to be lured back into his grasp. But the fact remains that Carrie sees Big as her soulmate, and no other guy ever really has a chance. They're all just temporary distractions until she and Big inevitably get to live happily ever after.

1. Aidan Shaw

Poor Aidan (John Corbett). Out of all the guys Carrie dates, nobody is better to her than he is. Not even Big comes close — at least, not until after they finally tie the knot. Aidan is an all-around wonderful guy, with a stable career, strong sense of self, and a whole lot of love for Carrie. The only real issues Carrie ever has with him are small ones. They're a great fit — except for the fact that he's not Mr. Big.

Arguably the worst thing Carrie does on the show is cheat on Aidan with Big. He gives her a second chance later down the line, and even tolerates Big showing up and crashing his weekend getaway with Carrie when he's heartbroken over a completely separate relationship. But Carrie ends up breaking Aidan's heart yet again when she realizes she just can't bring herself to marry him. The guy is a saint. Luckily, he ends up married to another furniture designer, with whom he has three kids.