It was during his customary mid-Pre-Calc hash break that he spotted her.

She looked like everything the words "Blair Waldorf" conjured up in the minds of the frightened underclassman: steely, haughty, and always, always, always perfectly put together.

He knew better. He saw past her perfect white ruffled shirt and her perfect navy pressed high-waisted A-line skirt and her perfect white tights and her perfect black patent Lanvin mary-jane flats and her perfect chocolate ringlets with the perfect black bow topping them. He saw that the usual bitchy flame in her eyes had been extinguished; that the hint of a smirk that was always plastered on her face had been lowered just a millimeter into a pursing, a pursing of her red lips that she thought fooled everyone into thinking that her life was just as perfect as always. And it was fooling everyone. She was good – she wouldn't be Queen if she wasn't so great an actress – but not good enough to fool him.

He should have told her about Nate and Serena as soon as it happened. But the next time he had seen her after the Shepherd wedding, her best friend had vanished, her father had run off with his male lover, and it just didn't seem an apropos time to say, "Waldorf, your boyfriend and best friend fucked on a bar and I watched… it was pretty hot, I'm not going to lie." So he kept it from her, and kept it from her, and hoped that when the truth finally came out, she wouldn't know that he had been aware of the indiscretion since the moment it occurred.

Of course, then at the brunch he just had to remind everyone that he was Chuck Bass and Chuck Bass is all-knowing, forgetting that she was standing right there until she looked at him and angrily choked out, "You know?" Only he knew that it was not a question, but an accusatory statement, and when she had stalked off muttering that she was "not even close" to being happy, he also knew that it was probably his fault. And for a second... he actually felt guilty. Seeing how sad she was about it, thinking about how he could have saved her the past six months of wondering why Nate wouldn't touch her, thinking about how she could have started moving on with someone who appreciated how witty and smart and delicate and fucking beautiful she was… but then Blair and her sad doe eyes were out of the room, and he remembered who he was, and he told Serena that his room was available, and everything was the way it was supposed to be.

Now, seeing her today at school, he knew he had to say something. At the very least, so he could have someone to banter with… Nate's idea of a "witty retort" to one of Chuck's comments was "that's what she said" or "whatever dude, your mom" and the last time Chuck made a reference to Humbert Humbert around Nate, all he said was, "Dude, like the egg in that story about the wall? Is that his full name?" before returning his attention to his lacrosse stick – the one with the "lax is life" sticker on it. And that is why he sauntered over to her, prepared to face the risk that she would punch him in the face.

"Waldorf,"

"Bass."

"What are you doing out here? Don't you have a teacher to be sucking up to right now? I wouldn't think that Yale accepts girls who cut class…"

"And I wouldn't think that any female in Manhattan would risk being infected with one of your myriad STDs, but sometimes even I can be wrong."

"Ouch." He was used to her vitriolic insults, but this time, she didn't seem to be joking. "Look, I was just curious as to why you were out here when I've never even heard of you leaving a class before. That's it, Waldorf."

"Well, Bass, if you must know, we are being lectured on The Great Gatsby and I am bored out of my mind. I hate the book."

"Why?" He couldn't stop the words from coming out of his mouth. "Hits too close to home?"

Fuck. Fuck, fuck, fuck.

"Excuse me?" She blurted. "Explain yourself."

"Oh, I think you know." He quickly regained his composure, or at least appeared to, and attempted a smirk. "The whole idea of a woman staying with her husband just to try and keep up the facade of a fairytale life, even though he's fucking some trashy whore on the side."

Way to kick her while she's down, Bass. He braced himself for whatever horrible thing she would say to him next, or a punch in the face, or even castration… but instead, he just saw her eyes flicker, and her face drop.

"That analogy doesn't fit, though… Daisy is blonde and beautiful, and Myrtle is short and squat and brunette." She bit her lip and stared down at her shoes. "If anything, she's Daisy and I'm Myrtle. Only no one would ever cheat on Serena van der Woodsen."

"Wrong, Waldorf," He knew his knowledge of literature would come in handy someday. "I have to say, I'm a bit surprised that someone as studious as yourself clearly has only gleaned knowledge of her English class reading assignment by watching the film version of the novel, but Daisy is supposed to be brunette. Gatsby references her dark, shining hair. You're Daisy, Blair."

"Great. I'm Daisy. So, my boyfriend is cheating on me, and I'm too pathetic to leave him, just like Daisy is. Thank you for this pep talk, Chuck, but maybe you should cross motivational speaker off your list of career possibilities and go straight to 'male prostitute.' I'm going to go."

"You could, Blair," Chuck stammered. "Leave him, I mean. It's not like there aren't other guys out there. It always annoyed me that Daisy didn't leave Tom for Gatsby."

"You're forgetting one crucial difference between me and Daisy, Chuck: I don't have a Gatsby," she said, almost ashamed. She picked her head up. "But when you find some unbearably handsome and absurdly wealthy – albeit new money – boy who has been completely in love with me for years, you let me know."

Fuck, sometimes she was so oblivious he couldn't stand it.

"Until then, I'm going to throw all of my energy into a) salvaging what is left of my relationship, and b) getting into Yale. So, if you will excuse me, I need to go back to doing what I do, which is diligently taking notes in class and being Constance's shoo-in for valedictorian, and you can go back to what you do – desperate girls with low self-esteem and probable Daddy issues."

He smiled in spite of himself. This was the Blair he liked to see; not the one who called herself "short and squat".

"Have fun in English, Blair. And while you're there – could you tell Penelope to meet me out here? I'd love for her to give me a hand with something…" He winked.

"Still disgusting."

"Still proud of it."

Blair rolled her eyes and turned her back to him as she started back to class.

"And Blair…"

She turned around exasperatedly. "What is it now, Chuck? Do you want to braid each other's hair?"
"I just remembered… it's Ivy Week."

"Yes? And?" She sighed, hands on her hips, tapping her foot impatiently.

"So… that whore is going down."

She gave him another eyeroll, but this time it was followed by a smile. Not a pout, not a smirk, but a smile.

And then she was gone.