During the first group outing of the new “Gossip Girl” reboot, a young man walks into a members-only club and sits next to his girlfriend, a social media influencer. He shares the Dan Humphrey-esque trait of being completely over whatever harebrained plans the wealthy teenagers may have, but projects his disdain with the confidence of someone who doesn’t doubt his place among the rest of them.

“If one-tenth of these people donated the price of one drink to a charity of their choice — ” he begins, looking around at other patrons with names as luxurious as his own, Otto “Obie” Bergmann IV.

“They are the charity of their choice, Obes,” his friend and high school classmate Max Wolfe cuts in, “and that one drink is to help them forget what people like you ask of them.”

Obie’s girlfriend, Julien Calloway (Jordan Alexander), identifies him earlier in the episode as the guiltiest of “the guilty rich,” a description to which Max (Thomas Doherty) adds, “And the richest.” That Obie (Eli Brown) is the one to criticize reckless spending as the wealthiest member of the group is as rich as he is, but also emblematic of a central conundrum: How do you make a soapy television show about out-of-touch Upper East Siders for a generation said to be more socially conscious than ever before?

The original “Gossip Girl” relished in its opulence, the spoiled teenagers tossing couture brand names around as often as they rolled their eyes. Their bank account balances were enviable; their lives and lack of morals not so much. The scandalous CW series came to recognize the limits of its storytelling, even adopting a tongue-in-cheek tone in the notorious marketing campaign pulling quotes from a negative review that referred to the show as “a nasty piece of work.”

Streaming on HBO Max, the reboot is a more self-serious affair. Showrunner Josh Safran, who wrote for the original series years ago, told Variety the new characters would “wrestle with their privilege in a way that I think the original didn’t.” In light of widespread protests last summer, he continued, and “even going back to Occupy Wall Street, things have shifted.”

They certainly have — from details as inconsequential as the new girl, Zoya Lott (Whitney Peak), facing mockery for a headband Blair Waldorf (Leighton Meester) would’ve coveted in the original series, to progressive developments like resident playboy Max sleeping with both men and women. In lieu of the power struggle between Blair and Serena van der Woodsen (Blake Lively), “Gossip Girl” stokes flames between newly acquainted half sisters Julien and Zoya, who share a dead mother but not much else.

Even the Gossip Girl mantle has shifted hands, given that its progenitor, Dan (Penn Badgley), has grown and embarked on a more prestigious writing career. In the reboot, teachers from Constance Billard and St. Jude’s, where the characters attend school, revive the secret-spilling website as an Instagram account and use it to distract and sow tension between their students, who apparently savor the challenge of banding together to get their instructors fired from already low-paying jobs for no good reason.

And so the show’s very premise hinges upon the teenagers willfully disregarding the financial security of their underpaid teachers, directly clashing with the promised wrestling with privilege. From the most cynical standpoint, even feigning interest in the labor issue at hand — or, at the very least, not causing it themselves — would better serve the aspiring and established influencers’ progressive brands (all while adding to the series a layer of timely commentary on performative behavior online).

Of the wealthy characters, only Obie expresses concern over the casual cruelty with which his peers treat those who aren’t of their social stature — namely Kate Keller (Tavi Gevinson), the young teacher who bonds with Zoya, a scholarship student whose presumably middle-class family can only afford to live in New York because of her late grandmother’s rent-controlled apartment. Obie defends Ms. Keller against Julien’s derision but, even with his influence as the so-called “Prince of New York,” stops short of actually advocating for the teachers. Are we meant to be endeared to Obie simply because he exhibits a shred of empathy for those less wealthy, or does his passive nature make him nearly as bad as the others?

Not even the most thoughtful teenager is flawless, of course, and gray areas in characterization can be a plus. But the reboot waffles with its approach to depicting the immensely wealthy, which lends a faltering tone more than it does nuance. Whereas characters of the Blair-and-Serena era weren’t often intended to be sympathetic figures, new additions like Obie — and Julien, who tries to make up for her misdeeds as the season progresses — at times appear to be aiming for both admirable and aspirational. The loose grasp for social consciousness dulls whatever sharp points stand to be made about the richest of their generation.

For this reason, the reboot’s pitch as “Succession” for Gen Z rings hollow. Both series exist under the WarnerMedia umbrella, which has carved out a niche by pushing out shows about terrible rich people. But with “Succession,” the HBO dramedy about a soulless New York family running a fictional media conglomerate, the biting criticism comes from the framing and style of execution rather than from the characters themselves. That the Roys remain oblivious to their heartlessness is the entire point.

There’s a certain level of ridiculousness viewers expect from “Gossip Girl” — especially given its CW origins — but the reboot seems keen on continuing down the self-serious path. With this in mind, it would do well to explore why it is Obie doesn’t believe he fits into the Upper East Side mold, interrogating his shortcomings as it does Julien’s self-centered behavior or Max’s impulsive tendencies. Even the reboot’s most charitable teenager deserves less charitable treatment.

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