It wouldn't be Gossip Girl if everyone on the show was a good person. Heck, fans would have died for Blair, despite of (or perhaps even because of) the fact that she was an elitist, entitled Upper East Side princess. Yet HBO Max's Gossip Girl revival is doing something a bit different. The characters on the new Gossip Girl are certainly scheme-happy, and love to revel in their wealth, but they're also far more aware of the problems that exist outside their rich kid bubble. And perhaps no one talks about these problems more than Obie Bergmann, the "prince" of New York City.

When we first meet Obie, he's handing out sandwiches to union protestors outside a construction site. It's a very Vanessa Abrams thing for him to do, and given how much Obie resembles Dan Humphrey, it's worth wondering if that's his role in all of this: Is he a Brooklynite (or insert whatever outer borough is getting scorn from the Constance Billiard crowd these days) who takes the bus to school and gets off on the fact that he's so much better than his peers?

Nope. Obie is, in fact, the most wealthy member of the clique, and very much in the in-crowd. At the beginning of the series, he's dating uber-successful influencer, and top of the social hierarchy, Julien. That construction site he was protesting? It was his parents' construction site. Because they're insanely wealthy developers.

Here's how a conversation between Obie and Zoya's dad, Nick, goes down:

OBIE: It essentially forces them out of this neighborhood and it leaves the area wide open for developers who are already circling.

NICK: Like your parents.

OBIE: Yeah, and everybody else who sees the Navy yard as a billion dollar property and not a neighborhood. I think that privilege ignores the reality of systemic issues.

NICK: I'm surprised to hear you speak about your parents this way.

OBIE: (Laughs) Well, it's nothing that I haven't told them. They support me. They want me to remind them. Keep them honest.

On face value, it may seem like Obie is doing the best that he can, given his circumstances. After all, it's not exactly his money (though he benefits from it greatly) and keeping his family "honest," while likely useless, is better than defending their predatory development practices.

Yet it's the way that Obie talks about his parents in this scene that I found potentially telling. He delivers the line to Nick without a hint of bitterness or resentment. It's almost like all of Obie's arguments about what his parents are doing to the displaced people of New York is met with a pat on the head — "Good for you for being so woke, Obie!" Despite Obie standing with union workers, "fighting" for justice, he's not seen as much of a threat to his parents' livelihood.

Except, if Obie were to really stop all of the overdevelopment of historic communities that he claims to want... it would be a threat to his parents' livelihood. Thus, major conflict.

And it doesn't so much seem like Obie wants that. He toes the line with his family — and, in a way, it's understandable, as he's still a teenager and they are his family — while still seeming like the most "woke" one of his group. He gets the best of both worlds: Obie can sleep soundly at night knowing he's not like his parents skyrocketing rental markets, while still having a $500 million dollar roof over his head and endless opportunities.

Yet... can this last? My theory is, no — and I think that the show is teasing that Obie's going to have a choice to make between his supposed morals and his family's money sooner rather than later. In Episode 3, Zoya dresses up for a night out to the theater, thanks to Luna's makeover. When Obie compliments her and seems thrilled at her transformation (which, to be fair, is like, green eyeshadow and a black dress) Zoya ponders if maybe he really is into all this Manhattan socialite stuff. She tells him, "When I showed up tonight and you liked how I looked, I thought when you said you wanted something different, you were already comfortable with something you know. The perfect picture by your side."

When Obie points out that he broke up with Julien because she became too much that "perfect picture," Zoya retorts back that maybe Obie had something to do with all of that. That Julien got lost behind Obie.

"It's hard to be with the prince of New York, when even he won't admit that's who he is," Zoya muses.

And this is why I think this season of Gossip Girl is going to be Obie's villain origin story. Obie can pretend that he's above all the money and the power that it brings him, but eventually, his parents may do something that really crosses a line — and Obie will have to choose between his moral high ground and aligning himself with his family. Right now, Obie's activism has no real impact on his family.

But if it eventually does? Well, I think Obie's going to choose to remain the prince of New York instead of the activist without a trust fund, putting him on the outs with new girlfriend Zoya and his former activist friends. It's an honest trajectory for most children of the extraordinarily wealthy — and that is a Gossip Girl story I'm dying to see.

Images: HBO Max