He sits with her, sad as she is, and thinks for a bit before smiling. "Do you remember when you used to make us watch your favorite movies over and over again? Like Tiffany's, and Holiday? It used to drive me nuts." Blair looks at him, a bit of that icy fire creeping back: "Is this a pep talk?" He grins and continues. "Well, I finally asked you why you liked watching movies you've already seen, and you remember what you said?" I like knowing how things are going to turn out. He smiles. "Exactly. You know, growing up, I never knew who I was supposed to be..." She looks at him, surprised as anyone once he starts talking; confused about what he's saying: "So I'd spend all my time apologizing for the privilege and the wealth and the opportunities I felt other people deserved more than I did." Almost crying himself, as the old, old shit comes up. "And you know what I'm finally learning? You can't fight against who you are. And you are Blair Waldorf." She smiles wonderfully, thanking him, and asks what happened to the old Nate Archibald, who just wanted to get high and play Halo. He laughs. He doesn't know.
Blair reconsiders him: he is good. He is off on a path parallel to hers, family in tatters, college almost insurmountable. He heads back inside; she opens her mouth to say one thing but offers him his jacket instead, with the sweetest smile. She looks at him, adoring him again, and he smiles a bit. And when he's gone, she straightens her back and tries to remember what it felt like, before everything happened. She is Blair Waldorf.
Serena finds Dan, and slaps him across the mouth before he can say hello; he's surprised into laughter, almost, asking why, and she starts strong: "I don't know, Newland Archer. Try to rack your brain a little." Dan realizes B told her about the thing with Rachel, and points out that they were broken up at the time, and still are. "Oh, so that makes it okay to have sex with a teacher?"
He points out that she wasn't his teacher, which is the wrong thing to say, because he knew how special she was to Serena, how special she made Serena feel: "No, she was mine. And you slept with her at school, during a play, with me probably twenty feet away." Dan agrees that it was sleazy, but he's caught out by something, some devious and wonderful smile lurking in the corner of her mouth. Why is she smiling? "I don't know! I'm mad! But that was invigorating!" Straight-up adorable. She jumps with a giggle as he laughs, charming as ever, and then notes the clutch of girls taking their picture in the corner. She shoves him affectionately, and drags him off to get some ice.