It Still Stings: The CW’s Sex and the City Prequel The Carrie Diaries Was Just Getting Started

By Jay Snow  |  April 3, 2024 | 11:35am
Photo Courtesy of The CW
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It Still Stings: The CW’s Sex and the City Prequel The Carrie Diaries Was Just Getting Started

Editor’s Note: TV moves on, but we haven’t. In our feature series It Still Stings, we relive emotional TV moments that we just can’t get over. You know the ones, where months, years, or even decades later, it still provokes a reaction? We’re here for you. We rant because we love. Or, once loved. And obviously, when discussing finales in particular, there will be spoilers:

For two seasons, The Carrie Diaries proved itself to be the pinnacle of what The CW had to offer before it all but abandoned the teen drama and became the DC superhero network. Starring AnnaSophia Robb as the titular Carrie Bradshaw of Sex and the City fame, the prequel series took us back to Carrie’s formative years in the ‘80s as she prepared to graduate high school, leave small-town Castlebury, and ultimately fall in love with New York City. Despite being canceled, the series remains an immaculate rewatch thanks to its lovable characters and storylines. However, what continues to be most disappointing about this ill-timed cancellation was that, in many ways, the story was only just beginning.

Though there was so much more potential if the series returned for a third season, that isn’t to say its existing two seasons didn’t provide some compelling stories and character development. This is no doubt in part due to a talented ensemble cast. Tagging along were Carrie’s childhood best friends Walt (Brendan Dooling), Maggie (Katie Findlay), and Mouse (Ellen Wong), who all faced their own unique issues while living in Castlebury and being tempted by much bigger things, like Manhattan.

Walt struggled to come to terms with being gay as the AIDS crisis developed, while Maggie (whom Walt had been dating for years by the time the series began) felt unloved, finding herself taken advantage of by an older police officer who worked for her father. Meanwhile, she tried to envision a future for herself after years of buying into her family’s belief that, as a girl, her purpose was to find a man and have children. 

On the other hand, Mouse had always been so focused on the future (and her inevitable time at an Ivy League school before becoming a doctor) that she hadn’t really discovered who she was. There’s also Carrie’s hunky love interest Sebastian (Austin Butler), the so-called bad boy with a heart of gold and deep pockets, who wants more from life than to follow in his terrible father’s footsteps. And, of course, who could forget Donna LaDonna (Chloe Bridges), the sex-positive “mean girl” who actually turned out to be one of the series’ best characters, developing a beautiful friendship with Walt as she was, for a while, one of the few who knew he was gay and helped him feel normal and safe.

So, as Carrie discovered what she wanted, including a future as a writer, it balanced quite well with her friends making similar yet wholly different choices about themselves, especially as the series had a bit more freedom with the other characters surrounding the iconic Carrie Bradshaw. All the while, it prioritized Carrie’s relationships, depicting her as a loyal, devoted, and empathic friend (unlike And Just Like That…). Plus, we had the pleasure of watching the wacky exploits of a young Samantha Jones (Lindsey Gort) throughout the second season, as her legendary friendship with Carrie began in the most unexpected of ways.

That said, something that boosted The Carrie Diaries to stand on its own were its not-so-rare decisions to break from the Sex and the City canon and pave its own path. The biggest example of this is Carrie’s family. Unlike in the original, Carrie has a little sister, Dorrit (Stefania LaVie Owen), who causes her quite a bit of strife, especially after their mother’s death that launches the prequel. They also have a very supportive father (again, unlike the original)—Tom (Matt Letscher)—who is completely devoted to them and trying to make sure they are prepared for their bright futures. The girls don’t make this easy for him in the slightest, and he crosses the line a bit by being too strict throughout the series’ 26 episodes, but when this family comes together, they provide some of the prequel’s most compelling and poignant moments.

In addition to changing her family, The Carrie Diaries also makes a major break from canon at the end of the second season. After Carrie and her friends graduated from high school in Connecticut, Carrie was planning to take a full-time job at Interview Magazine—where she had interned under Larissa (Freema Agyeman) for the last two years—instead of going to college at NYU. But, when Larissa was fired and her job fell through, Carrie then learned she wouldn’t be able to register for classes at NYU until spring (at best). So, with her friends by her side, Carrie finally moved to New York City to work as a waitress and pursue her dream of becoming a writer alongside her friends.

Going forward, the series would have broken free of high school with Carrie stepping into her own as a young woman, with a devoted group of friends, finally and fully embracing what the original was all about: living and finding yourself in New York City. The series could have become a bit more mature, which would have been perfect considering the direction that The CW headed after The Carrie Diaries was canceled in 2014. Truly, the series was just getting started and had a unique opportunity to tell a new story with Carrie Bradshaw and this fantastic ensemble cast, which is why the cancellation still stings more than a decade later.

Jay Snow is a freelance writer. He has published many places on the internet. For more of his thoughts on television and to see his other work (or to simply watch him gush again and again over his love for the original Charmed) follow him @snowyjay.

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