They meet for an old-times coffee on the odd day when they're both in the city. She looks stunning, like always, in a sweater and jeans and she orders them pancakes, but all Nate wants is caffeine.

It's a forced, tense nine a.m. meeting, with an impossibly perky waitress and a folk guitar soundtrack cracking over the loudspeakers in the background.

And he can't escape the memories. Because she is The One.

'How are you supposed to know,' Nate wonders, 'when you're fifteen and she's sixteen, and you're so wholly engaged in the open bar that there's somewhere between three and five of everything in the room—how are you supposed to know when the time is right?'

Because confessing your love to a best friend in the middle of your cheating sex-a-thon in the back room of a wedding isn't exactly the traditional way to resurrect such a delicate topic.

Although, all things considered, there could be worse moments to bring it up. Such as his own wedding. Not that Nate did that. Not that Nate even considered doing that. Not even a tiny little bit. Not even when she was the last to leave and they sat together at the bar and she was missing an earring and her make-up smudged across her face and she still sparkled about seventeen times more brilliantly than anyone, even the bride.

Serena had a habit of doing that, you know.

But he didn't tell her then. And he wasn't about to tell her now. In fact, he didn't tell her anything at all.

It's not something they prepare you for, falling in love. Nate never took a class on the aftermath of betrayal, it wasn't the kind of thing they offered in the course catalogue at St. Judes. He never read a textbook on the nuances of cheating, or took a quiz on how to handle his numbing teenage desire.

So no one ever told him to be ready, because, no matter how drunk you are, no matter how many hundreds of miles off your map the moment arises—it's your moment. And you only get one chance, one shot to win the girl. Even, as Nate later learned, if it's not the girl you always thought it would be.

Of course, Nate doesn't realize all of this until years later, after they don't end up together, but instead loiter on opposite coasts leading opposite lives. It's too late now, and that's that.

But he was just fifteen, after all, and not such quick-witted fifteen—did anyone really expect him to pick up on the fact that 'This Is It,' and 'Alright now Natey, you'd better fire on all cylinders because you just had sex for the very first time and She Is The One.'

Besides, how was he supposed to know that he—it—wouldn't feel like this with Blair. Maybe it was just a result of the motions and not the mechanic. But by the time he disproved this novel hypothesis it was far, far too late.

He wasn't ready when he should have been ready, but who would have guessed that after they finally, finally, finally—who would have guessed that—Nate didn't expect her to up and disappear for a year. He was given quite literally a moment to rip out his heart, and he missed it, and then she was gone. And she never even said goodbye.

Not that she didn't come back eventually—but nothing was the same. She wasn't his Serena anymore, she was some other Serena. Dan's Serena, maybe, or possibly Blair's Serena. And Nate wasn't recklessly in love with Blair's Serena; he was in love with his own.

It was his moment but he missed it, because he was fifteen and stupid, and didn't know how to handle the fact that this was his moment and her name wasn't Blair.

It was his moment but he missed it, but at least it wasn't for lack of trying. Because Nate tried to tell her. He really, truly did.

Except Nate was fifteen, stupid, and drunk, and his "I love you" got jumbled up somehow on the way to his mouth and tripped out instead as "I think I'm going to throw up."

"Me too," she said, shaking her head with half a laugh and running her hand through her matted drape of hair.

It wasn't until years later, as they sat, face-to-face at that old brunch place on 77th and Lexington, and she smiled at him from beneath that ethereal hair, bringing a bite of heavily syruped pancake to her delicate mouth—it wasn't until then that he realized Serena would have said the same thing either way.

But it wasn't her moment. It was Nate's moment. And he missed it.

A/N: So, I broke my one ultimate cardinal rule (haha, well other than writing Serena/Dan) and I wrote a future fic. But I mean, come on guys, it's not really a future fic! It's got all sorts of past SerenaNate!Sex angst and the likes. Not that any of you care.

Anyways, I don't think I'm satisfied with this. I hope it makes sense! Sometimes I've got all these ideas in my head but they whine and complain and flat out throw tantrums about getting out onto the paper. So I normally just give up and go "ugh, fine wtf whatever." and call my work complete. This is one of those times. Not that any of you care.