The new “Gossip Girl” doesn’t understand Gen Z. “The White Lotus” does.

It’s fitting to start this newsletter with a discussion of “Gossip Girl,” one of the most iconic teen shows of my generation. The show was based on Cecily von Zeigesar’s book series of the same name, and adapted by wunderkind Josh Schwartz, on the heels of his freshman series success, “The O.C.” In many ways an east coast adaptation of that series, “Gossip Girl” followed the exploits of uber-rich teens Blair Waldorf (the amazing Leighton Meester), Serena van der Woodsen (Blake Lively), and their other horrible wealthy friends, frenemies, sworn enemies, and romantic interests. All were followed around by a mysterious blogger (it was 2007) who sent mass texts on the latest gossip to the characters on their Blackberries. It was cynical, scandalous, and true to its messaging—“every parent’s nightmare,” its first season ads announced, splayed over images of Blake Lively in apparent orgasmic ecstasy. 

I revisited the pilot episode of “Gossip Girl” after watching the first few episodes of its HBO Max reboot, which, as many reviewers have noted, falls strikingly flat. I’ve spent an embarrassing amount of time trying to pinpoint just why the series fails. Other TV writers have pointed to a number of factors: it’s boring; it gives away its mystery too soon; there’s no logic to the decision of making the teens’ schoolteacher be gossip girl. Its attempted wokeness is forced and not believable. As Robert Lloyd wrote for the LA Times, “mentions of “the patriarchy” do not lead to plot lines about smashing the patriarchy so much as they reflect adult writers’ awareness that the patriarchy is something a smart teenager might inveigh against in a television show.”

I’d add that despite the fact its two lead women are biracial, the show suffers from a sort of mid-aughts race blindness (see: “Pretty Little Liars,” another teen show that will certainly be mentioned in this newsletter again) I’d hoped TV had left behind. 

While “Gossip Girl” (2007) falls squarely into the realm of millennial TV, the reboot struggles to capture the specificities and hypocrisies of politically progressive Gen Z-ers. The new “Gossip Girl” features the same entitled, bratty teens featured in its predecessor, only now they say things like “don’t straight shame me” and “may I have your consent,” in the midst of trying to seduce their teachers or their friends’ boyfriends. One of the characters, Obie, is the personification of rich guilt, who in one cringe-y scene explains to his new girlfriend’s father, a middle class Black man, how much he opposes a new waterfront development, despite the fact that his parents are real estate tycoons. 

I thought about the new “Gossip Girl” while watching another new HBOMax series, “The White Lotus,” a prestige miniseries by Mike White which recounts the experiences of the mostly white, mostly very wealthy guests at an upscale resort in Hawaii. Although it’s a very different kind of show than “Gossip Girl,” both feature uber-rich characters behaving badly who demonstrate varying levels of self-awareness about their privilege. Two of the characters, Paula (Brittany O’Grady) and Olivia (Sydney Sweeney), are disaffected college sophomores who read Freud and Proust by the pool, an image that has instantly become a meme. Olivia is daughter to Nicole Mossbacher (Connie Britton, one of my favorite TV actresses), who made a fortune as the CFO of a major search engine a lá Sheryl Sandberg. 

Olivia and Paula are pure Gen Z, pure “dirtbag left.” They are sardonic, disaffected, and bleed socialist politics. (Although in one scene, Nicole contends that Olivia’s politics are purely “cynicism.”) Whereas in “Gossip Girl,” the only difference between the Gen Z students and millennial teachers is that their teachers are poorer, disrespected, and don’t understand TikTok. But “White Lotus” digs deep into the generational clashes between Olivia and Paula and its other characters, millennial newlyweds (too earnest, too traditional) and their Gen-X/boomer parents (too puritanical, too capitalist). They talk openly and explicitly about sex, in bored monotone. They make fun of Nicole for loving Hillary Clinton. And when the girls lose Paula’s purse full of drugs she brought to the island, Paula claims it contained some of her research for her thesis on “colonialism.” The irony of course being that they are on a resort in Hawaii.

“White Lotus” catches Olivia and Paula in a specific moment of undergrad pretension, as their choices of beach reads confirm. (Although the politics of the books they’re reading are questionable. Thumbs down, Camille Paglia; thumbs up, Judith Butler). At the same time, they act like teenagers. Olivia is inexplicably cruel to her younger brother, jealous of her friend’s romantic exploits, goads her parents on for no reason, whines ceaselessly. Many of her conversations with her parents, Nicole and Mark, revolve around their political clashes with their daughter, who they see as blind to the fact that it is Nicole’s capitalist success that has given Olivia the opportunities she’s gotten. When Nicole says something Olivia finds offensive, she retorts, “what are you going to do? Cancel me? Dox me? Sic the K-pop fans on me?” Both mother and daughter are equally dismissive and belittling of the others’ beliefs.

Dinner conversations revolve around these generational clashes. These exchanges become more tense when Paula questions Nicole and Mark, who appear unaware that Paula’s experience as a woman of color might be different from their own. But despite her anti-capitalist pretenses, Olivia also seems similarly unaware, and her casual cruelty, jealousy, and pettiness towards her friend increasingly threatens their friendship. “Woke” or not, money blinds them to the contradictions and hypocrisies they enact. There’s certainly enough drama there to hold the viewer’s attention, which is more than can be said for the new “Gossip Girl.”

The new “Gossip Girl” has none of the Gen Z specifics or generational culture clashes of “White Lotus,” and its tone shifts wildly. In the eyes of characters like Olivia and Paula, everything is a complex waiting to be unpacked and critiqued. Yet a scene in which Obie (Eli Brown) takes his new girlfriend, a middle-class biracial Black girl named Zoya (Whitney Peak) to a store after hours to buy school supplies for underprivileged kids after skipping out on a black-tie fundraiser for the same cause, is meant to come off as sweet and admirable. Just like that, rich guilt can be absolved! The working class storeowner smilingly watches the two lovebirds cavort in the aisles of the store that Obie paid him to reopen after hours. It is cringeworthy. 

It’s worth noting that “Gossip Girl” (2007) was never cooked up to be an HBO prestige drama or Emmy-bait.  It knew what it was: a teen soap on the CW. That’s why it’s especially odd that the new series is on HBO, and seems stuck between the original series’ fun rompiness while vaguely trying to poke at deeper ideas. As a result, neither effort works. The original “Gossip Girl” is filled with snappy zingers delivered dripping with disdain. The new one speaks in tongue-twister platitudes.

But perhaps most importantly, the new “Gossip Girl” is no fun to watch. Its drama feels strangely unmoored from any momentum, each scene shapelessly bleeding into the next like an ill-fitting piece of couture. It’s also easy to forget what happened from scene-to-scene, because its writers have thrown everything at the wall but nothing sticks. Its script has little bounce, and lacks the bantery exchanges of the original series an the gravitas of Leighton Meester. If the show intends to skewer wealthy Gen-Z-ers, it needs to understand what they are actually like.

Read about the roots of my weird obsession with teen TV, and why I started this newsletter.