Before Aidan Shaw broke Carrie Bradshaw’s heart and before Mr. Big was "The One" for the fifth time, there was Skipper Johnston. Remember him? Probably not. If you rewatch the pilot of Sex and the City today, his presence feels like a glitch in the Matrix. He’s the sweet, awkward, wildly sensitive "nice guy" who served as Carrie’s platonic foil during the show's embryonic phase.
Ben Weber played the role with a specific kind of 1998 jitteriness. He was the guy who believed in "The One." He was the bridge between the cynical, high-fashion world of the four women and the reality of being a lonely guy in Manhattan. But by the time the show found its footing and its Manolo Blahniks, Skipper was gone. He didn't just leave; he evaporated.
The Weird Logic of Skipper in Sex and the City
Skipper Johnston was introduced as a 27-year-old creator of a website—a "web developer" back when that sounded like a futuristic job title. He was the anti-Big. While Big was a glass of scotch and a dark suit, Skipper was a fleece vest and a nervous stutter.
Honestly, the chemistry between him and Carrie was fascinatingly weird. They were close. In the first few episodes, he is effectively her "gay best friend" before Stanford Blatch fully occupied that narrative space. Skipper represented the "New Man" of the late 90s: vulnerable, communicative, and constantly terrified of being dumped.
His main arc centered on his obsessive, often toxic relationship with Miranda Hobbes. It’s a dynamic that feels incredibly dated now. Miranda, the cynical lawyer who prided herself on being "above" emotional messiness, used Skipper as an ego boost whenever she felt lonely. It was a power imbalance that wouldn’t fly in a 2026 reboot. He was obsessed; she was bored.
Why the Character Actually Disappeared
Most fans assume Ben Weber left for a better gig. The truth is more about the show’s DNA changing. As Sex and the City evolved from a quasi-documentary style (remember those awkward interviews with random New Yorkers?) into a glossy, aspirational dramedy, there was no room for Skipper.
The show became about the core four.
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Adding a fifth wheel who wasn't a love interest for the long haul just cluttered the frame. By Season 2, his appearances dwindled. By Season 3, he was a ghost. Darren Star and Michael Patrick King realized the show worked best when the "men" were either rotating guest stars or serious obstacles to the women's independence. Skipper was neither. He was just... there.
The Miranda Problem
The relationship between Miranda and Skipper was the show's first real attempt at exploring "settling."
Think about the scene where Skipper is actually having sex with another woman—a woman who actually likes him—and Miranda calls him. He dumps the girl mid-act to run to Miranda. It’s pathetic. It’s also very real. We’ve all seen that guy. But for a show that was trying to empower its female leads, having Miranda string along a "nice guy" started to make her look less like a boss and more like a bully.
The Evolution of the "Nice Guy" Trope
If you look at Skipper through a modern lens, he’s a fascinating case study. In 1998, he was framed as the "sweet one." In 2026, he’d probably be called a "simp" or criticized for his "Nice Guy TM" energy. He felt entitled to Miranda’s affection because he was kind to her.
He didn't have the rugged charm of Aidan or the intellectual wit of Robert Leeds. He was just Skipper.
But there’s something nostalgic about those early episodes. The grainy film stock. The lack of smartphones. Skipper sitting in a dive bar talking about "the internet" as if it were a niche hobby. He represented a version of New York that was still a little bit gritty and a little bit unpolished. Once the show moved into the era of the $500 cupcake and the $1,000 shoe, the web developer in the fleece vest had to go.
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What Ben Weber Did Next
Ben Weber didn't disappear, even if Skipper did. He went on to have a very solid career as a character actor. You’ve likely seen him in The West Wing, Entourage, or as the face of those ubiquitous "Caveman" commercials for GEICO. He has that "guy I know from somewhere" face.
But for a certain generation of HBO subscribers, he will always be the guy who got left in the 20th century.
Interestingly, when And Just Like That... premiered, there was a tiny subset of the fandom hoping for a Skipper cameo. Maybe he sold his website for billions? Maybe he’s a jaded tech mogul living in a penthouse? It didn't happen. The creators seem content to let Skipper remain a relic of the pilot era.
The Legacy of the "Forgotten" Friend
The disappearance of Skipper Johnston taught us something about how television is made. Pilots are experiments. Characters are discarded like draft pages once the "vibe" is established.
He serves as a reminder that Carrie’s circle was originally wider. She had friends who weren't just the three girls. She had a life that felt a bit more integrated into the actual social fabric of New York. As the show became a global phenomenon, that circle tightened until it became an airtight vacuum.
If you're doing a rewatch, pay attention to the way Skipper looks at the world. He’s the only character who seems genuinely surprised by the cynicism of Manhattan dating. Everyone else is a pro; Skipper is an amateur.
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How to Spot Skipper in the Wild
If you want to track the exact moment the show outgrew him, watch the transition between the end of Season 1 and the middle of Season 2.
- The Style Shift: Notice how the lighting gets warmer and the clothes get more expensive. Skipper’s wardrobe stays stuck in 1996.
- The Dialogue: The "man on the street" interviews disappear. This was Skipper's natural habitat.
- Miranda’s Growth: Once Miranda starts dating Steve Brady, the "Skipper" slot is filled by someone with more narrative weight. Steve was also a "nice guy," but he had a backbone and a bar.
Moving Forward With Your SATC Lore
Understanding Skipper is key to understanding why the early seasons feel so different from the movies or the reboot. He was the anchor to a reality that the show eventually decided to leave behind in favor of high-fashion fantasy.
If you want to dive deeper into the "lost" era of the show, your next step is to look at the original columns by Candace Bushnell. The real-life Skipper wasn't just a character; he was a composite of the types of men hanging around the New York media scene in the mid-90s—men who were technically savvy but socially adrift.
Check out the episode "The Turtle and the Hare" (Season 1, Episode 9). It’s one of the last times Skipper feels like a core part of the ensemble. After that, he’s basically on borrowed time.
For those looking to truly master Sex and the City trivia, don't just focus on the shoes. Focus on the people who didn't make the cut. Skipper Johnston was the first casualty of the show's journey toward becoming a cultural icon. He was too normal for a show that wanted to be legendary.
To see how the show changed, compare the dialogue in the pilot to the dialogue in the Season 2 finale. You'll see a shift from "real talk" to "quips." Skipper was a "real talk" guy. He just didn't have the punchlines to survive the shift.
Go back and watch those first twelve episodes. Look past Carrie’s curls and Miranda’s overalls. You’ll see a guy in the background, probably holding a beer, wondering why nobody is calling him back. That’s Skipper. And in a way, he’s the most relatable character the show ever had.
Next Steps for Fans:
- Rewatch the Pilot: Note how much screen time Skipper gets compared to Charlotte. It's jarring.
- Research the "Caveman" Ads: See if you can recognize Ben Weber under all that prosthetic makeup.
- Read the Bushnell Columns: Find the specific mentions of the "New York geeks" that inspired Skipper's archetype.