Bedford rooftop, where Chuck's already mid-sneer: "Brooklyn?" Blair, trying desperately to pump herself up as quickly as possible for this, is like, "At least it'll be memorable?" What will? The fairytale. "I'm sorry, but don't you have something you want to say to me?" He smiles at her romantically as she says she does... Humphrey Lesson Four: Never, Ever Trust. Her lips are sealed. She tries to say it but nothing comes out. She shakes it off. "...This is so silly. What does it matter who says it first? Why don't we just say it together?" Chuck informs her that wasn't the deal, but he means that there's still the chance that she'll open her mouth and nothing will come out, and his words will hang there in the silence for a moment, before her laughter joins it, and then he really will jump. The history of his love goes: dead unknown Mom, ice-cold Dad, Nate who dumped him, all the women he can fuck. How can he possibly trust right now? Especially the only person as good at this as he is?
"Why does everything have to be a deal?" she asks, flirty, and he responds less so: "Because we made it one." She swallows, panicking and he asks her WTF is going on. What's the trick here? What's the game? "You told me you had something to say to me." There's pain in his voice: "Say it." Blair completely loses track of everything, with Dan's voice echoing in her head: "Why do I have to be the one to go first? I was the one who waited on that helipad for you. I went to Tuscany alone..." Chuck swears it's ancient history and she keeps reeling it off: "...I was the one who asked you to say it first!" Chuck points out that this was at the White Party, in the middle of her running away from him as fast as she could into a fairytale of her own devising: "Did you really think I was going to say it then?" Of course she did. It was the only thing that could have saved her, and she was begging for it. It rips itself out of her: "YES!" She begins to cry. "And when you didn't, I wanted to die." I love you, I love you, I love you. Why do they have to say it? They're saying it all the time.
Chuck tells her to drop it because he didn't come to Brooklyn for the litany of the ways they've hurt each other, the way he followed Marcus around for days on days trying to crack him, the way he aimed Serena and Blair and Dan at each other and destroyed them for the meager, nasty half-satisfaction of loving her under cover of night, away from the real world and her shame, only to be treated as something repulsive for the affront of simply loving. He's lowered himself too, and she knows it. "I thought you were ready to tell me how you really felt. Obviously it was just another one of your games." Blair's tears: are they real? Who can tell? "My games? You're the one who started this," she cries, but it's not good enough. "And you're the one who finished it," he says, turning away from her. Short of dropping to her knees, then, she takes him at his word and leaves. And just as she is leaving, he turns his head to see her gone, so he must take her at hers. It's not something happening to her, it's something she's working with him to build.