Warning: Dair angst. Get out tissues if you get all emosh from these types of stories.
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He's 15 the first time he sees her, and he doesn't really see her.
He's too busy jumping in front of taxi's to save the girl he thinks he's desperately in love with, and feeling hypnotized by her golden hair and the way she twirls. He knows the slightly shorter, definitely meaner, and in every way different brunette that stands by the blonde's side is Blair Waldorf, but in reality he doesn't pay enough attention to her.
His 15 year old brain is too fixed on the girl of his dreams he can't help but not notice anyone else.
.
She's really not that bad. He realizes that soon after he becomes a part of their world, the ultimate insider. He finally lands the girl of his dreams but soon finds that things aren't all blonde manes, laughs and red roses with Serena. It's difficult, complicated and intense, and sometimes he just wishes things were simpler.
He begins to know the brunette a little better, sees that behind the Queen B act and mean streak she's just insecure and going through exactly the same things he is. A broken family, broken love, broken heart. Those things aren't easy to fix and whilst he writes them away she keeps them locked up inside, slowly pushing them out through the form of angry remarks or two fingers stuck up her throat and out down the porcelain toilet bowl.
She's human just like the rest of them. And she actually has a great heart.
.
It's not until the Summer when it's only them in the city out of their (very dysfunctional) group that they discover they have even more in common. She likes insightful documentaries, long museum tours, decorative arts and expressive literature, just like him. In some ways he's glad that he's found someone that he can share those interests with, but at first he wishes it isn't Blair Waldorf that's on the receiving end of his monologues about how vivid the French documentary on Lynette the Orangutan at film forum is.
He gets to know her the months following, really know her. They share their deepest secrets, he'd fathered a kid that was not really his and she was sold for a hotel by the person she still deemed the love of her life. They find themselves stuck in the present whilst Chuck Bass and Serena van der Woodsen seem to be able to able to move just fine without them. All they really have left are each other.
.
They kiss once. A test really, at least that's what they convince themselves it is. Just to see if the impossible really happens, if Dan Humphrey and Blair Waldorf really feel something for each other.
And the result is a bit different to expected. Well not for her, she runs off and finds herself a prince and gets caught up in him and suddenly she's engaged and running off to Monaco with her fiancé Louis and planning her wedding and he's left stuck in the past again except this time all on his own.
He wants her after the kiss. After all his years running after her blonde counter-part thinking that she was the girl he wants he realizes it's Blair, it's always been Blair. He was just too blind to see it.
And when he does he's already lost her.
Though he always knew he'd never stand a chance at having her. She's Blair Waldorf, Queen of the Upper East Side, and he's Dan Humphrey living in a small loft on the wrong side of the Brooklyn bridge.
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She doesn't end up married, she runs away at the alter and Dan watches in horror from his place near the front that she's allocated for him. Chuck Bass runs after her and suddenly it all makes sense to him.
As if she'd ever marry someone that wasn't Chuck.
But something goes wrong and they don't get back together. Serena's out of town having problems with her dad again and he's the only one there, he knows that, but he doesn't care, because when she shows up at the loft crying, he's still glad that he's were she came.
Turns out she's pregnant. Or rather was. Miscarriage, Chuck's baby (no surprise there) and it's killing her, and he cries along side her and sleeps next to her, drying her tears throughout the night.
.
They kiss again and this time it's different. This time their lips lock and they continue locking and she doesn't run away when they pull away, or attempt to convince herself it doesn't matter, or that she doesn't feel anything for him.
She pulls him right back towards her and they fumble towards the bedroom, knowing that this is the first time in a long time that that things have felt alright.
They last three whole months before someone finds out. A Gossip Girl minion spots them making out in the lobby of the Waldorf's (they were becoming sloppy) and then everyone suddenly knows. Blair surprises him pleasantly, she doesn't make a fuss, just says that she assumed it would all come out eventually anyways.
She'd already told Serena the week prior apparently, and the blonde gave them her blessing happily. He pretends that the fact doesn't hurt, but it does, especially when he catches sight of Chuck Bass watching them and knows that Chuck would never give them his blessing. He sometimes feels that what he had with Serena, what anyone has with anyone, is nothing when compared to the complexity, and intensity of BlairandChuck, ChuckandBlair. Sometimes he just feels like another stepping stone in the epic love story that is Chuck and Blair.
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His father's surprised (to say the least) and so is the rest of Manhattan because Waldorf's don't date Humphrey's, or rather prissy princess's don't date Brooklyn boys but Blair's not like that, maybe she never was, but he sees that now, he sees her for who she really is. And they're happy, they're really really happy.
Until he messes it all up.
It's Vanessa's fault really, she even manages to screw up his life whilst all tucked up a million miles away in Spain. She published the book and even though it was anonymous somehow Blair stumbles across it and he realizes the dangers of writing so closely about his friends and family.
She cries and she leaves him and he brakes down.
He doesn't expect her to turn up on his doorstep two days later, pushing her lips onto his telling him that she read the end. That she loves him too.
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Two years, two engagement rings rings, and five break downs later and she walks down the isle.
He watches her with tears in his eyes, thinks that she's never looked more beautiful, that the smile on her face has never looked so genuine, thinks that she's never looked more happy.
Not even with him.
He watches from the back this time, not at the front like at her first wedding, this time she didn't allocate him a seat, she doesn't even know that he's there. But he turns up.
Like she'd ever marry someone that's not Chuck Bass.
They were destined, soul mates, each others eternities. True Love.
He bought her a ring the year prior but it wasn't enough. They weren't enough, they weren't meant for forever.
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His fifty the last time he sees her and he's finally seen her. He doesn't see anything but her.
He's too busy jumping in front of a taxi to save the brunette girl he knows he's desperately in love with to realize it's the end. He feels hypnotized by her chocolate brunette locks and gorgeous mahogany red painted smile.
She's got a family now, a husband and kids and she deserves it (though he'd be ying if he said he never wished that it was him she woke up to). His brain's too busy on over load to realize that's it's not like 35 years ago. He hasn't just saved Serena van der Woodsen and begun his life – it's the beginning of the end now – he's saved Blair Waldorf and sacrificed himself and he doesn't even know it.
His 50 year old brain is too fixed on the girl of his dreams he can't help but not notice anything else.
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I'm determined to write something that has a Dair happy ending. Mark my words.
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