Jenny comes out in a black smock dress, off the shoulder with a Holly Hobby hemline, cute but too Jenny, and Poppy smile squints and straight up says they prefer the other one. Jenny, feeling railroaded and/or tempted, agrees to try the other one on, and Poppy laughs because she feels vindicated, and tells Serena to start making calls. So Serena does, wearing a complicated mass of chains around her neck, because she will do anything you tell her to do as long as she knows it's the next step in being the girl she wants to be.
I mean, I don't think of her as a lightweight, because what happened was, she called up Poppy and said, "Fix this," and now Poppy's fixing it, which is to Grownup Page Six Serena as dating Dan was to Good Girl Serena. And of all the high school/grownup/identity crisis parallels in this episode, I think Serena's is the best because she's totally doing it with her eyes open: how do you make your life look the way you want it to? Ask an expert, follow their advice. That's way better than Dan trying to get control by condescending to the poor misguided fan letter guy, or Nate dumping Vanessa for being the Marxist free-trade cricket on his van der Bilt shoulder, or the Lord Marcus/Colony Club redux shit Blair's pulling for the eightieth time, or Jenny thinking that you're only an individual if somebody's watching you nonconform, or Rufus and Lily blindly groping their way toward parenting and adulthood as usual.
Vanessa comes into a diner where Nate's waiting, looking sad. She's all about how grateful she is that he agreed to meet her, and how great it is to see her, and he's like, "Not so fast, cowboy." She gives him the puppydogs, for some reason, and he reminds her that she's the one that left. She begs with her eyes, hoping that things aren't the way they appear, that she's not been sitting around waiting for him to call while he's been quite happily moved back to Blair. And of course, he has no idea that she's sitting there with his morning coffee burnt into her retinas, so he is playing it straight: they broke up, it was essentially her choice, and he's not got a lot of regrets about it.
I feel for Nate even more than usual in this episode, because he honestly is trying to do things the right way, but there are all these factors he doesn't know about, so nobody's reacting right. Nate knows Blair's laying in wait around every corner waiting to pounce, and before he can even deal with that he's got to clean up these loose ends, plus the fact that the life he's now returning to always had Blair in it, which is kind of a downward slide, but also easy. So he's got two problems, which to him are completely separate except in the most vaguely conscious way, but everybody else believes -- because Chuck is playing both Vanessa and Blair in different ways -- that they are the same problem. Which means whether he likes it or not, or understands it even, they have become the same problem, because Vanessa can't dig her way out of it and Blair doesn't want to.