While there are moments in the Sex and the City series that feel timeless, there are harsh realities of rewatching the series 26 years later. The show follows a group of friends in their 30s and 40s living in New York City in the late ’90s through early ’00s. It focuses on their friendship and their experiences dating in the city, focusing on their long-term relationships as the show progresses.
The show is based on Candace Bushnell’s novel of the same name. It was originally published as a series of newspaper columns for The New York Observer, and the show follows a similar premise. When picked up for television, Bushnell becomes the fictional character Carrie Bradshaw, played by Sarah Jessica Parker, and her friends become the fictional characters Samantha Jones (Kim Cattrall), Charlotte York (Kristin Davis), and Miranda Hobbs (Cynthia Nixon).
After six seasons of will-they/won’t-they from Carrie and Mr. Big, the couple ends up together at the end of the original Sex and the City series. The first Sex and the City movie even saw Carrie and Mr. Big tie the knot. The harsh reality here is that Mr. Big wasn’t worth the hype when looking back at Carrie & Mr. Big’s relationship timeline.
There are plenty of moments when the drama between the couple is enough to call it quits for good, like when Big marries Natasha between seasons 2 and 3 after telling Carrie that he doesn’t want to get married again. Then, in season 3, Big tells Carrie that he wants out of his relationship with Natasha, and the events that follow are why Carrie and Aidan break up twice.Mr. Big is a big doozy, not marriage material.
Although there were plenty of instances to find fault with her boyfriends throughout the years, Carrie was her own worst enemy in Sex and the City.There are times when Carrie’s reaction doesn’t help the situation, like in season 1, episode 12, when Carrie flakes on her trip with Big because she believes he refuses to integrate her into his life. She gets the idea because Big hesitates to introduce Carrie to his mother, among other ways that he’s reserved in their relationship.
Carrie is paranoid, and she shows up where he is taking his mother to church. When surprised by seeing Carrie, Big introduces Carrie as a friend to his mother, even though they have been dating. Although it’s valid for Carrie to get what she needs from Big in order to move forward, it’s hard not to wish she would just have taken a deep breath, gotten in the cab, and resolved some of her concerns when they got to their destination, since the couple would spend five more seasons working it out.
Another relationship that’s worth a second look with a Sex and the City rewatch is Miranda and Steve’s. With a rewatch, it’s clear that Miranda & Steve’s relationship was always doomed. The pair meet at a bar where Steve bartends, and their relationship begins with bickering and a one-night stand. Steve slowly attaches to Miranda as he courts her, eventually convincing her to get a puppy and let him move into her apartment despite her refusal.
The chemistry between the pair pales in comparison to the compatibility of Miranda’s relationship with Dr. Robert Leads, a sports medicine doctor for the New York Knicks, but Miranda leaves Robert in the middle of Brady’s first birthday party as she succumbs to her feelings for Steve. It’s evident that the relationship was never good for either of them, and it reaches its romantic conclusion in the And Just Like That spinoff.
Rewatching the original Sex and the City series, it’s evident that Charlotte loses some of her character’s more adventurous qualities after her devastating marriage to Trey MacDougal. Before her marriage to Trey, Charlotte was one of the more adventurous friends, which was evident when she went all-in with her gallery work. After Charlotte marries Trey, she is in for a messy divorce brokered by her to-be husband, Harry Goldenblatt, and falls for Harry shortly after her divorce.
Charlotte’s more adventurous side shines in season 1, episode 5, when renowned artist Neville Morgan shows Charlotte his paintings of the vagina and asks Charlotte to pose for him, and she agrees, or in season 3, episode 4, when Charlotte dresses as a man and is photographed by Baird for his Drag Kings: A Collision of Illusion and Reality exhibit at her gallery. Although Charlotte gains new qualities as a wife and mother, her adventurous side has yet to fully reemerge in And Just Like That.
There’s a simple explanation for Samantha and Smith’s Sex and the City breakup, but the reality is that their relationship worked beautifully in New York, whereas it didn’t work in California. Samantha descends into a deep state of unhappiness after leaving New York to further Smith’s acting career in Los Angeles, causing her to leave Smith and focus on herself, witnessing their chemistry and friendship in the original series is bittersweet. Their charming partnership signals that Smith is the one who got away.
The narrative that Samantha loves herself more than she loves Smith at the end of the first movie is empowering, but it’s only because she gives herself so completely to Smith’s career that she loses herself in the first place. If Samantha and Smith had stayed in New York, Samantha would not have given up her work, city, friends, and lifestyle all at once, and her relationship would have had more balance. It’s natural for Samantha’s conclusion to be an independent woman, but it would have been more full-circle for her character to end the series that way rather than the first movie.
There’s no question the original series lacked diversity, which is one of the major flaws of Sex and the City. When diverse perspectives were represented, they were often trivialized as a plot point for the main cast, or the end of a joke. A prime example is Stanford Blatch and Anthony Marentino, who comprise most of the show’s LGBTQ+ representation. The characters are mostly utilized in the narrative as a sounding board for Carrie and Charlotte and lack depth in their own storylines. Stanford barely finds relationship satisfaction throughout the series, and when he finally does, he marries Anthony.
With Carrie’s lavish lifestyle choices, it’s still conceivable that she could afford her Upper West Side apartment in late 90s New York with her freelance writing income. It’s hard to conceive that in today’s economy, Carrie Bradshaw, as a freelance columnist, could earn enough to afford her lifestyle, considering her prime real estate and all the designer tags she has in her closet. While possible, Carrie was able to take it pretty easy some days, and it doesn’t necessarily match the pace of a freelance writer working in New York City today.
One of the harshest realities of rewatching Sex and the City is how much the city in question has changed since the show aired in 1998. The late 90s New York in Sex and the City was a world before 9/11, and before cell phones and social media, and the characters’ lives have a simplicity to them that doesn’t exist today. The show’s characters experience communication blunders due to being locked into landlines, but they also have the freedom to explore their world without constantly being tied to the other characters who affect their lives.
When rewatching Sex and the City almost three decades after it first aired, some of the hardest moments to watch involve Samantha’s character. In season 3, episode 9, for example, Samantha uses derogatory language directed toward the trans sex workers loitering outside her apartment when they are making too much noise outside her window at night. While requesting the neighbors keep it down is one thing, Samantha’s dealing with the situation embodies hate.
Samantha also uses derogatory language in season 3, episode 5, when she is dating Black music producer Chivon, played by Asio Highsmith. When she gets in a fight with Chivon’s sister at the club, Samantha uses racially insensitive language that is offensive and disrespectful. Although she is one of the most beloved characters from the original series, Samantha has some moments that her character needs to redeem herself from if she ever makes a more permanent reappearance in And Just Like That.
For a sex columnist, there were a lot of times that Carrie wasn’t very sex-positive, or was too quick to judge the men she was dating. One of the most memorable examples is in season 3, episode 4, when Carrie is dating Sean, who reveals to her that he is bisexual and had a relationship with a man. As Carrie is unable to conceive that Sean is attracted to both men and women, she’s constantly insecure in their relationship and openly writes off Sean’s sexuality (as a sex columnist) by assuming that Sean is probably just gay.
She is also quick to judge the politician she dates in season 3, episode 2, who asks Carrie to pee on him when she instantly dumps him and then writes about it in her column. She shows the same behavior toward the musician she dates in season 4, episode 4, who she dumps for having ADD. Although there have been memorable and justified relationship endings in Sex and the City for Carrie,some of Carrie’s relationships end because she can’t leave her comfort zone.
Sex and the City was a progressive show for 1998, making the franchise iconic for decades to come. However, some elements have not aged well 26 years later. The characters have questionable behavior and relationships, but that’s one of the things that makes the original series great. There were things that the series could have done better, and some of those antidotes to the original storyline have played out in the spinoff show And Just Like That. While Carrie’s erratic lifestyle is one of the aspects that makes Sex and the City, time allows room for improvement.