A/N: First of all, I do not own Gossip Girl. Second, this is my first ever fan fiction so no flames please, although constructive criticism is appreciated. Thanks for reading & I hope you enjoy it!

Chapter One: Another Failure

For as long as Chuck Bass could remember, he'd known he loved Blair Waldorf. And he'd also known that she could never be his. Chuck's first memory was a testament to this.

He was five years old with a crop of short brown hair, a miniature scarf and eyes that spoke of manipulative intelligence. It was the annual Bass brunch- the room was buzzing with carefully orchestrated conversations and loud, false laughter. Chuck surveyed the room; his amusement illustrated by one raised eyebrow. A statuesque blond was desperately trying to stop her small blond daughter from climbing onto a table whilst the equally blond baby boy on her hip began to wail. She smiled apologetically at the couple seated across the table and the woman nodded a sympathetic reply whilst simultaneously elbowing her partner, who was lost in conversation with the handsome waiter.

At that moment, the hairs on the back of Chuck's neck rose as he instinctively registered that he was being watched. He turned his head to meet the unrelenting gaze of Blair Waldorf's large, doe eyes. Even as a child she appeared haughty, perched elegantly on the plush dining chair. Chuck was both disparaged and intrigued. A vision of dark curls and expensive clothing, she was completely alone. Chuck took a tentative step towards her. By now, the girl was no longer watching him. Free from her withering stare, Chuck quickened his pace and crossed the room to reach Blair's table.

"Chuck Bass," He extended his small hand towards Blair, holding his breath for her response to his impromptu introduction. Blair hopped down from the chair, with as much grace as is possible for a small child to have when hopping. She looked down at Chuck's hand, as though assessing its suitability. For one terrible moment, he thought she would refuse it. But Chuck Bass had underestimated the petite brunette.

"Blair Cornelia Waldorf," She said in return, lightly clasping his hand with her own before quickly releasing it. "This must be your brunch, then."

The smirk that had been spreading across the young boy's features vanished at her words. "It's my dad's, actually. I didn't want to come. These things are always so boring."

Blair's eyes widened in shock. "You are heinous. Our parents only throw these events so we can have fun." Her tone was a mixture of practiced outrage and self-assurance.

"You're having fun?" Chuck's eyebrow shot up as his smirk also returned, his face now the image of childlike malice. "Sitting here all alone. Bet nobody would ever want to have fun with you."

Blair's brown eyes welled up with fat tears as Chuck felt an ominous hand on his shoulder and gulped nervously. Chuck could get his own way with everyone, except his father. The couple that Chuck had observed earlier appeared at Blair's side. The man stooped down to Blair and she buried her dark head into his shoulder. Meanwhile, Blair's mother looked from her daughter to Chuck with equal disdain.

"Charles, can't you be trusted for one brunch? I'm sorry Eleanor; my son refuses to learn the social graces that Blair has picked up so well." Chuck's father's voice was stern and Chuck looked up at him with regret. The young boy tried constantly to impress his father and failed on every occasion.

"Forget it, Bart. Let's just enjoy this wonderful brunch. Blair is far from perfect. Harold, take her over to the Archibald's table. Nate will cheer her up. They do get on so well." And after a brief air-kiss between the parents, the Waldorfs were gone. Bart looked down at his son and sighed, before turning on his heel towards a crowd of glamorous women. Chuck resumed his observation of the room, admiring the fabricated warmth between the Waldorf and the Archibald family as they greeted one another. A knot in his stomach tightened as he watched Blair untangle herself from her father to address a small boy with a mop of golden hair. The two children shot nervous glances at each other before the boy muttered something to Blair which made her giggle. Chuck quickly looked away.

No one noticed as Chuck slunk under the table cloth to his private oasis. As the little boy crouched under the table, trying to block out reality, he rewound the event which had just taken place. If things had been different, Blair might've been hidden away with him, giggling with Chuck instead of the Archibald boy. But Chuck had failed again.