UES socialite Blair Waldorf had met Daniel Humphrey in less than perfect circumstances. Only later would she realize she had actually met him once before, him running, boxer clad, from her best friend Serena's bedroom one evening when Blair had stopped by the van der Woodsen penthouse unannounced. The second time they met, the one she remembered him from, involved Georgina Sparks asking him to buy them both a drink at a bar in Brooklyn. Blair had been lied to about the evening's plans and she stood in the dingy watering hole in Calvin Klein silk and Gucci flats, feeling very put out. There was an emo boy in eye liner wailing into a microphone on the other side of the room and Blair wouldn't even dare put her clutch down on the table for fear of what diseases might be on the surface. Georgina laughed and her eyes sparkled. How had Blair ended up with G (of all people) as her NYU roommate, she couldn't figure out. Must be punishment for her myriad of schemes and revenges. Karma was as big a bitch as Blair, it seemed.
And so this man, scruffier than Blair trusted, in a plaid button up and ripped jeans (not artfully ripped, just old and torn) came to say hello to G and had been asked to buy them drinks. He came back with three cans of Pabst Blue Ribbon, which Blair had never even heard of and tasted like what she thought very old dishwater might, but she sipped at it to be polite. He was the only one in the venue speaking to them after all, and he did smell nice despite his appearance.
When he offered to drive them home, Blair was surprised and accepted even when Georgina scoffed and said she may spend the evening in Brooklyn but that didn't mean she didn't have her driver waiting around the corner. Having already accepted, Blair scowled at G but refused to spend another moment in her company.
The ride home was tense. Wanting more than anything to mock his clothing, his posture, his music (he had preformed a couple of songs on an acoustic guitar - very clichéd), his hair, and his vehicle, Blair chose instead to keep her mouth shut and let him talk. At length. As a matter of fact from the time they hit the bridge until he pulled up in front of her building he hadn't hardly stopped for breath. Yes. Dan Humphrey was a little too scruffy, rumpled, and energetic for Blair's taste but when he surprised her by asking if she'd like to have a drink sometime, something other than a can of beer he said, she surprised herself even more than he had, and said yes.
Blair found herself breaking her own rules before long, for him. Sleeping without her eye mask. Braving the subway to see him play. His father had been a musician and it seemed, with his raspy blues voice and deep affection for the guitar, that he'd picked it up along the way. But Dan considered himself a writer and the music was good, as much as she loathed admitting it. She found herself happy after years of dysfunction in a tug-and-play game with a fellow UES trust fund baby. She found herself hardly thinking of Chuck Bass as she wore jeans and let her curls hang loose sans headband and watched indie flicks at little movie theaters where those from her social circle wouldn't know him. She slept well, next to Dan Humphrey. Curled up on his couch in a loft in Dumbo. And so it went. For six months they weren't friends, weren't more that either of them would vocalize, but there was sleeping and conversation and Blair smiling and it was simple.
She came to need their time together. Her time away from the politics of philanthropy and fashion and long histories of deceit.
And then he played a song for her, about an old soul who just couldn't break free. About a girl he wanted to love but who had her plans and her schemes and her real life to get back to at the end of the movie. And she melted. Serena leaned in during the song and said to her in a stage whisper: "You are so screwed. You're never gonna be able to quit him because you'll just see him play and you'd be all starry eyed again." It was then that Blair knew it had to end. She had plans and schemes and a reputation to uphold and real life to get back to at the end of the song and if Serena of all people could see, it was time to end things.
She told him so and the look of disappointment on his face disgusted her. She said, "Really, it's been nice not being friends with you," wistfully.
As he left, without his permission, his lips moved and his tongue formed words and he was saying to her: "You know, it all played out differently in my head."
A small ending compared to illicit affairs and broken engagements, secret lovers and formal dances, and yet it would be the ending that would haunt Blair as she walked down the aisle a year later, promising herself and her heart to a prince among men. A real Prince, as a matter of fact. And a song stuck in her head as she says I do, wondering if a lonely boy musician in Brooklyn was watching the society pages and maybe knew the mistake she was making.