Carrie Bradshaw is one of the most iconic television characters to emerge from the late 90s. When HBO’s Sex And The City burst onto the small screen in 1998, fans could not wait to tune in every week to see how the sex columnist and her four friends would handle the landscape of the New York City dating scene. Given the fact that she writes about love for a living, Carrie’s love life is anything but perfect. It’s messy, complicated and sometimes, just downright toxic.
Fast forward 20+ years and a new generation is getting introduced to Miss Bradshaw and her dating woes, thanks to film sequels and syndication. With recent rumors about a potential revival for HBO Max now is the perfect opportunity to open up her little black book and revisit some of Carrie’s most memorable former flames.
10 Least: Alexander Petrovsky
Also known as The Russian, Carrie meets Alexander at an art exhibit. He’s a celebrated artist who frequented Club 54 and was somewhat of a playboy back in the day. When the two start dating, he appears to be a cultured intellect who introduces Carrie to luxuries like fancy coffee, horse-drawn carriage rides and Russian cuisine. He eventually convinces her to quit her column, leave her friends and move to Paris.
Once they arrive in the City of Lights, he becomes neglectful and absent. The final straw is when he slaps her across the face during a heated argument. The act is unforgivable, and Carrie realizes that she has lost herself in the façade and that she needs to remain true to herself.
9 Jack Berger
Jack Berger is a writer with a knack for crafting fiction and a talent for being a downright jerk. Besides the fact that he and Carrie have compatible senses of humor, they lack a certain amount of chemistry that leaves room for conflict. After his latest novel receives lukewarm praise, his jealousy of Carrie’s success turns him spiteful.
He cowardly dumps her via an infamous Post-it note and leaves her without an ounce of closure, proving that this is one chapter of Carrie’s life that should remain closed.
8 Vaughn Wysel
Throughout SATC, Carrie dates a handful of fellow writers, and the first one viewers meet is Vaughn Wysel (played by Justin Theroux). When Carrie develops a close relationship with his family, things start to dwindle. He projects his own insecurities onto Carrie, which exposes his fragile masculinity.
It’s fair to say that his family’s frankness revolving around conversations about intimacy might be crossing the line. Still, he definitely could have handled the situation with a lot more maturity rather than place all the blame onto Carrie.
In season 2, musician Jon Bon Jovi makes an appearance as Seth, a photographer and potential love interest for Carrie. The two meet in the waiting room of their mutual therapist, Dr. G. Their first date starts innocent enough. He’s conversational, honest and seemingly sweet. Things take a turn for the worse after they play a flirtatious game of Twister at her apartment.
After sleeping with women, Seth confesses that he loses interest in them right away, which deflates Carrie’s hope that she’s met a solid catch. He gets points for being honest but also loses some for not being upfront before things escalated.
6 Wade Adams
When Carrie meets Wade, a comic book store owner, he appears to be a grown man with a youthful heart. It turns out he still lives at home, smokes a little too much and suffers from a severe case of Peter Pan syndrome.
Yes, he’s fun and provides Carrie with a sense of escape, but he will never be mature enough to be a dependable partner. In the end, Carrie has to cross him off as a quick fling who helps her revisit her teenage age years and be carefree.
5 Billy Kelley
Billy Kelley, portrayed by Mad Men’s John Slattery, is a politician and running for treasurer. He brings Carrie along on his campaign trail, and the two develop strong chemistry. But Kelley’s got a secret under his sleeve, and throughout a couple of episodes, it becomes clear that this guy might be heading towards political scandal.
Eventually, the truth emerges in the form of a request in the bedroom. Understandably, the ask is too adventurous for Carrie and leaves both her and SATC fans voting “NO” on this relationship.
4 Mr. Big
One of the most well-known television couples is Carrie and Mr. Big. Over six seasons, the show spends a lot of time covering the tug and pull of their on-again and off-again relationship, resulting in a devastating affair and lots of other instances of heartbreak. Yes, she and Big are end game, but there’s a reason he’s called Mr. Big and not Mr. Right.
He’s secretive, dismissive and non-committal. By the end of the series, Big finally comes to his senses and realizes the errors in his ways. However, his years of stringing her along don’t make it easy to forgive and forget.
In episode 10 of season 6, “Boy Interrupted,” David Duchovny plays Jeremy, Carrie’s old high school boyfriend. After reuniting, one issue pops up: their dates have to work around his mysterious curfew. Later on in the episode, Carrie learns that Jeremy is a patient at an out-of-state psychiatric hospital.
It’s nice to see that he’s prioritizing his health and it shows that he’s probably more empathic than many of her past significant others. The timing of their reunion doesn’t work out, but Jeremy does the right thing by putting his well-being first.
In episode 3 of season 2, “Freak Show,” Carrie starts seeing an editor named Ben. He seems nice and, more importantly, normal, especially considering that Carrie is researching an article about whether or not there are any sane eligible men left in Manhattan. Carrie gives in to her lack of faith and ends up rummaging through his apartment, trying to find something that will reveal a secret or expose a freakish quirk.
In the end, Ben has no skeletons in his closet, which is sad because, as far as the audience knows, his only flaw is that he has a Tweety Bird tattoo.
1 Most: Aidan Shaw
Although Sex and the City features a slew of awful exes, it also has its share of great partners: Charlotte’s husband, Harry Goldenblatt, Miranda’s spouse, Steve Brady and Samantha’s boyfriend, Smith Jared. Then there’s Aidan Shaw, Carrie’s best boyfriend. The furniture designer is kind, loving and above all, patient.
After an affair with Big, the two split, reconcile, get engaged and end in another messy breakup. By the end of SATC, Aidan finds love and starts a family, while Carrie and Big reunite. Even though they both get what they want, it’s tough to watch poor Aidan’s heart go through the ringer time and time again. Yes, Aidan is perfect, just not perfect for Carrie.
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