"You pretend not to be like us, but you are, to the bone."

These words still resonate in his mind to this day. Only two years ago, this small sentence made him question who he really was. Was he the ultimate insider? Was he still hiding behind the mask he had put on to actually belong in this extravagant, yet exhausting world? Or was he just being targeted by an insecure girl falling from her reign because of a selfish man afraid to feel anything he had never experienced before?

To say he rose through the ranks would be an understatement. The son of an artist and a dwindling rock star who appreciated the simple things and saw people for who they truly were, and the sister of a naïve girl so determined to belong and change when really her goals and aspirations would lead to her inevitable downfall.

And her, his first love. How she came into the dull picture that was his life would be inscribed in his notepad forever. The night when he first saw her was a revelation and reminder of how he would never be worthy or lucky enough to have someone that mysterious, that wonderful all to his own.

Her family, her whole life was a constant whirlwind of excuses, drama, and money. At first, it seemed like it was a sign that he had to work and fight for this woman, this goddess that he still wonders to this day how he was even chosen to be hers.

It wasn't enough.

He put so much into the relationship only to receive nothing in return. The only thing he still has of her are the bittersweet memories that once clouded his mind every minute of every day.

But there was someone who never made excuses for who they were.

Someone that knew him so well, he even learned things about himself from her.

Someone he could talk to and be understood and not ignored.

Someone like her.

Brunette curls and Chanel N 5

This is the story of an outsider fighting for a way in, like his sister. Someone who valiantly stood up for the right thing and came from humble beginnings. But once he found his way, he realized it wasn't all it was supposed to be.

It didn't feel right being on the inside.

It was once again autumn on the Upper East Side. The leaves falling on the pavement symbolized new beginnings, as well as an ending to the warm haze of summer. A young boy walked on the sidewalk observing everything around him hoping to miss anything important as he normally did. He loved the simple things. He loved to witness small moments in a person's life, a smile shared with another or maybe a kiss with a lover, all the same.

Dan Humphrey was a nobody. If he had it his way he wouldn't be a sophomore at St. Jude's, but his parents had saved any money they had for his tuition, to finally have a Humphrey have a good education and solid future. Every day he walked the same route to the bus hoping his life would take a much needed turn for the better.

The bitter chill in the air signaled a cold winter ahead, but he was more concerned about the icy personas of his classmates who he would have to put up with for another two and a half years. It will all be worth it when I get into one of the best literary schools, he always thought, it will be worth it. To Dan, it was worse being ignored than to be hated and ridiculed. It was nice being acknowledged even if it was by people you have never spoken to in your life.

Walking along the streets reminded him that he was in fact, not alone. He was in Manhattan for crying out loud, one of the most populated cities in the world. It was a melting pot where anyone could find their niche, the place they truly belong. This didn't feel like it to Dan, but he was now used to it. However, his sister Jenny would be entering this frightening arena next year, and he was actually really worried about her.

Jennifer Tallulah Humphrey was a go-getter. She was the ultimate social climber, always checking her laptop for the latest celebrity gossip, watching Entertainment Tonight, and sketching clothes in her Lincoln Hawk notepad, courtesy of Rufus.

Jenny wasn't like Dan, sure they shared similar qualities having grown up together with the same humble values that shaped their very characters.

The annual Halloween party was coming up. An excuse for all of the Constance girls to whore it up and not get in any trouble for it. Somehow in all of this madness, he managed to get an invite. He wouldn't pass up the opportunity to take a look inside this world he was so fascinated with. Jenny however, would not be attending this one, she didn't need to mix into this crowd just yet.

Taking a deep breath, Dan continued on. Back home, back to his simple yet wonderful loft where he could be himself but was still left wondering what it would be like to be one of them. Just for one day.