A/N: I don't remember who asked for this, but somebody requested a fic where Dan reflects on his relationships with both Blair and Serena and that's what this is. It takes place about a year after 5x24. Kinda sad/depressing, but that's what Dair does to me sometimes. It's a conversation with a bartender, basically.
-Let me guess, this is about a girl.
-Two of them, actually.
Dan sits at the bar, a row of empty glasses in front of him. The writing doesn't come as easily anymore, usually ends up an endless stream of FUCK until he slams the laptop shut altogether. It's weird now, to think about high school and the person he used to be; so awkward and alone, and characteristically lonely. Maybe he's finally returning to his true self.
-Do you want to talk about it?
-They loved me, I loved them.
-It's a little bit more complicated than that, isn't it?
-Yeah.
He doesn't answer his phone anymore. In fact, he couldn't even tell you where his phone is if you asked. He figures it's under one of the many piles of useless shit in his apartment that he doesn't have the motivation to sort through. He used to have all of his stories and writings organized- which in high school meant a huge stack of ramblings about a reckless blonde with a twinkling smile who welcomed him into the Upper East Side with open arms. Next to that stack was a collection of angry scribbles about her bitchy brunette best friend whose only goal in life was to make his life miserable.
He starts by telling her about Serena, and the same image keeps flashing through his head. She's fifteen years old, dancing on a table at a party that he definitely was not supposed to be at. All he could think was, "God, I love her." Love at first sight. It's a tricky thing because you never catch everything at first sight, it takes sight after sight after sight after sight….
-She sounds like a great girl.
-She is.
He doesn't know how to describe Serena, because words don't do her justice. He ripped her apart in his first book for reasons that he doesn't completely understand, because Sabrina is not the person he fell in love with. Sabrina is not Serena and yet, Serena is a lot more like Sabrina than she would care to admit. He ripped her apart, and he can still remember the look on her face when she came to him, asking, "Do you even remember the girl you fell in love with?" If he would've been completely honest, he would've said, "No, I don't."
-So why did you break up?
-Which time?
Nate, Carter, Tripp, Aaron, Ben, ect. It gets harder and harder to love someone the less they choose you. Dan would like to say that he enjoys the chase, but it's more than that. He loved Serena and that was an aspect of his life that he thought he'd never lose, but people grow up, they change. They're not Romeo and Juliet, and if they were, they'd both be dead by now.
-Do you miss her?
-Sometimes.
He ran into Serena once after he returned from Rome. It was a complete accident, not something he would like to relive. As soon as her eyes landed on him, her face paled. His probably did the same. "There is no us. There's only you." No, Dan could not remember the girl he fell in love with, because she didn't exist anymore. Standing across the street from her, he had so many things he wanted to say, but he turned in the other direction and walked away before he had the chance to say any of them.
-Wait, then who's the other girl?
-Her best friend.
He starts to tell the bartender about Blair, and her eyes widen, because Blair sounds like the side character in some cheesy romcom about him and Serena. Of all the people to fall in love with, he had to choose Blair Waldorf. But of course, he didn't choose to fall in love with her. He was forced. She plowed over him like a bulldozer and he just lay flattened wondering if he would ever recover from her. She was everything to him. Then she was nothing to him. There's a gap in his heart where Blair was supposed to stay, forever. She probably will, but Dan doesn't like to think about that.
-So that's it? You fell for her best friend.
-She was the love of my life, but I wasn't hers.
If there's anything that Dan genuinely wants, it's to forget what it feels like to love Blair. He's learned what being consumed by love feels like. He had fallen for Serena, the epitome of sunshine and all that is happy. And then he had fallen for Blair, her brunette counterpart who's heart was darkened from letting men constantly dictate her self-worth. Dan thought he could show her what it was like to be loved selflessly, to love her the way she loved everyone else in her life.
It wasn't enough.
He had been back in New York for two months when he bumped into her at a charity event, something Nate had persuaded him to attend. His breath hitched when he saw her in her flowing black gown and as much as he wanted to turn and run, he knew he would have to face her eventually. Her hand touched his arm so gingerly that it almost made him want to cry.
"How was Rome? I tried to call and email, but you never replied."
"Did you really expect me to?"
"Don't tell me you're still mad at me."
Her doe eyes made him want to melt, but he refused to let her see the overwhelming affect she still had on him.
"I'm not mad at you, Blair. That would require me to feel something for you, and I don't. Not anymore."
He kept his gaze locked with hers, and she swallowed carefully. In the past few years that Dan had known Blair, he had learned how to read her. He knew when she was faking a laugh, holding in a cry, biting her tongue to stop from saying something rash, everything that was important to know about the person you're dating. Blair never learned those things about Dan, and when she looked at him that night, he knew he had convinced her. She would never know the ache that was punishing his chest just from looking at her.
-So what happened? It's just over?
Dan never saw them after that, but he'd hear stories here and there from Nate. Blair and Serena stopped talking. They wouldn't even look at each other when attending the same gala. Blair couldn't forgive Serena for sleeping with her boyfriend, again. Serena couldn't forgive Blair for…yeah, Nate hadn't figured out what Serena was mad at Blair about, but nonetheless, Dan felt partially responsible for their friendship's destruction. He used to dream about being Nate Archibald, having the two most beautiful girls at Constance playing a game of tug-o-war, with him as the rope. It's not all it's cracked up to be.
He wrote his second book while he was abroad. He meant to tear Blair to pieces, to point out every flaw that he knew would destroy her emotionally, but he couldn't do it. Instead he wrote a story about a girl and her dad, incorporating every story Blair had ever told him about herself and Harold, exaggerating for comic effect, but keeping them surprisingly accurate. He drops it off at the penthouse one day, when he thinks she's at work, and leaves it on the table in the foyer.
The title is "Pumpkin Pie and Princesses" with a small note attached that said, "I'll never tell you who you are, but this is who you'll always be to me."
She called him crying seventeen times. Too bad he can't find his phone.
