Prologue

The second time Dan Humphrey spoke to Serena Van Der Woodsen was also the first time he spoke to Blair Waldorf– or more accurately, she spoke at him. It was Thanksgiving and in true Humphrey style all was at risk for the lack of a single pumpkin pie. Dan had volunteered to rescue them from the jaws of disaster and had emerged onto New York's sidewalk, victoriously carrying a pie in a box and informing his mother of that fact, when he saw her.

Serena Van Der Woodsen was strolling across the road to a fanfare of shouts and horns. She appeared completely unaware of the fact that one yellow cab squealed to a halt, narrowly avoiding hitting her, and a second that was not going to make it in time.

Dan's heroic attitude came to the fore instantly. He hung up the phone, ran into the road and spun Serena out of the way, dropping the pie he'd just acquired. He took a moment to mourn as the cab driver drove on, screaming abuse at them both.

Serena continued to walk, one of her arms in the air. Dan hurried after her, completely confused by her behaviour.

"Hey, uh, excuse me!" he called, stopping shy of touching her. "Do you need a crossing guard?"

She looked at him, her eyes unfocused, as a cab pulled up beside her. She stumbled towards it, pointing.

"Or a cab, maybe?" Dan watched her with concern.

Serena then caught sight of Dan's fallen pie. It had been run over in the seconds since Dan dropped it to save her. "Oh, pie!" she complained, slurring slightly.

"More like road kill now, but better it than you! Right?" Dan joked nervously.

Serena finally looked at him, truly focused. She looked stunning in a green dress with a leopard-print coat, but the stench coming from her was that of smoke and alcohol. Dan didn't care.

"I'm Dan. Humphrey," he added, offering her his hand.

Serena grinned as she shook it. "Hi."

"Hi," Dan gushed. "Uh ..." he was momentarily taken aback by how beautiful Serena was. "We met last year?" he enquired, seeing her attention, already scattered, being attracted by several different things over his shoulder. "You might not remember ... Yeah, you probably don't but you should be more careful –"

"You need to keep your hands off her!" Blair Waldorf had arrived, clutching two purses and looking at Dan as though he were something on the sole of her shoe. Dan felt the urge to chuckle. The best friends were chalk and cheese; oil and milk; light and dark. While Serena was a sparkly, lively blonde, Blair was a determined, refined brunette. She was also sober and taking charge of Serena with the skill that came from practice.

"Blair!" Serena squealed excitedly.

"Trying to take advantage of her over the holidays," chided Blair, giving Dan a firm look of disdain. "Come on, let's go Serena."

She dragged her best friend to the waiting cab and tried to stow her inside it.

"Bye Dave!" waved Serena as she obeyed Blair's hands.

"Bye," Dan sighed deeply. Blair cast him one more look with narrowed eyes, and then folded into the cab with the grace Serena had not shown. "Bye Serena," Dan whispered mournfully. The cab pulled away, running over the pie once more. There was a kind of irony to it, Dan realised, as he stared at the mess on the tarmac.

He had no idea how important one of the women in the cab would become.

Dan's crush on Serena had been born a year earlier during his freshman year on October 18th, when he had been mistakenly invited to a birthday party and she was the only one there to speak to him. He ignored the fact that she was rebellious to the point of illegal and used her family's money to facilitate said behaviour. To him, she was perfect. Such is the blindness of young love.

As for Dan, he was a nobody. His parent's insistence that he attend private school for his education had made him the poor outsider within the confines of the Upper East Side society. The rich children had been taught to look down their noses at Dan Humphrey from Brooklyn, and Dan found that he hated them all. Particularly someone as snobbish and self-important as Blair Waldorf. It didn't surprise him that Blair had no idea who he was. What was disappointing, Dan mused as he surveyed his crushed pie, was that Serena didn't know him either.