I own nothing.
All characters are Gossip Girl.
Inspired by the Great Gatsby by F. Scott Fitzgerald.


August, 1920

"I love you, I love you so much," she whispered, the tears threatened to fall, her small hands clasped on his jacket, knuckles turning white.

A deep breath, "Well, that's too bad,"** he pulled her hands away from his jacket and broke eye contact and all body contact, he turned around and tried to ignore the sob that escaped her lips and jumped on the train, slamming the door shut behind him.

The girl fell to the floor, the commuters narrowly walking passed her, sobs racked her chest and her hands found the floor.

The boy on the train didn't look out the window again until the train departed, "You needed to get out of this town, she'll still be here when you get back," the man opposite him told the young man, patting his shoulder and offering him a drink.

He was not seen nor heard from again for six months.


July, 1922

Chuck smiled, "Well what is it you want to know, Humph?" he twirled his scotch in his hand, "Who the best bootleggers are? You might turn me in, but you'd be dead before you got to the phone," he knocked back the tumbler.

"I want to know everything, you, Blair.. what is going on?"

"You want to write about me? What about the petty little tit bits you've found out this evening?" Chuck smirked.

"I'll change the names, this is a story Bass. It'll be a work of fiction," Dan knew he was onto something, he pulled a small notebook and pen from his breast pocket.

"I'm the love of her life," Chuck drawled apathetically, "and I let her go."


It was 1912. Chuck Bass was ten years old and the best man at his Father's wedding. His new "Mother" was Lilian van der Woodsen, a beautiful socialite whose husband William van der Woodsen had left her bankrupt and jumped ship to Europe. Bart and Lily had always been acquainted and came up with the idea that a marriage of convinience would solve all problems - her and her children would have money and social standing and Bart would have the family man image that Bass Industries Head so desperately needed.. and not a word of the van der Woodsen scandal would come out.

Chuck was in a smaller version of his fathers black pinstriped suit, his father demanding that he be on his best behaviour that day - no comments, no pranks and no purple. There was press here for Goodness Sake! The next day on the front of the New York times stood the newest and most powerful family in New York.

It was on this Spring Afternoon that he was introduced to a Blair Waldorf. A small brunette girl with large doe eyes and a sharp tongue. Serena - his new sister introduced her as her best friend in the entire world. Chuck pulled Blair's hair twice that day. And she kicked his shins so hard he had bruises for weeks.

"B this is Chuck - my new big brother!" she smiled, Serena was currently missing her two front teeth.

Blair quirked an eyebrow, she had a large white bow in her chest nut curls, her mother had dressed her in a white Broderie anglaise and dolly shoes, "Nice to meet you, Charles," Blair was less than interested in the cretin that her best friend's new brother. She didn't need any more friends, she had minions.

"Charmed," he smarmed. He put out a hand to shake her hand, Blair looked disgusted and stomped off.

"Ignore her, she's just shy," Serena explained.

"Hmph," Chuck moaned and ran up to her and pushed her over into a flower bed. Soil, grass and flower stains all over her white as snow dress, "I'm sorry, I didn't see you there," smirking.

Blair didn't cry, she'd been taught not to cry in public, "You'll regret that," and she strutted off back to her mother.


When Serena, her younger brother Erik and Mother moved into the Penthouse of the Palace that afternoon, Chuck moved into the suite 1812. Chuck liked the solitude and he wanted to do as he pleased. Not many ten-year olds moved into their own suite but Chuck's reasoning "It's my trust fund, I'll spend it as I please," a Nanny checked in every hour.

Until that day, Chuck had only one friend - Nate Archibald. He was the son of ex-military Captain Howard Archibald and Anne Archibald - nee van der Bilt. From a long line of politicians, royalty and upperclassmen. The two had met as babies - the nannies who cared for them as infants took them to Central Park together. The boys grew up in eachother's homes, Nate's was a home like a museum, beautiful, cold and you couldn't touch anything* and Chuck was a sanctuary for debauchery.

Nate was blonde, blue-eyed and naïve, his life's ambition was to make his Mother smile. Something Chuck couldn't understand - not only just because he hadn't had a mother since an hour after his birth - but because he thrived on giving his father that vein that popped out the side of his head when Chuck was returned back to the Palace by the Community Warden or another Nanny handing in her notice abruptly "That child in the anti-Christ! He needs to be sent to a convent!"

Chuck Bass and Blair Waldorf were not eachother's biggest fans. They fought, bickered and picked on one another. Chuck used to pull her skirts up and Blair would in return take scissors to him dressing closet. The only reason Blair even put up with the scoundrel was because her Father Harold Waldorf took a shine to the boy. Nate wasn't intelligent enough for Blair - when they spoke she would get bored with his monotonous tone of "Yeah, I sailed today," Serena liked his simple ways, so Blair occasionally humoured him - "Wow, I never knew there was so much to rowing,".

When Bart and Lily had gotten enough image and money from each other they parted ways - although Lily in the divorce requested that Charles stay in her guardianship - Bart couldn't refuse! At least the boy would have some discipline.


Chuck was 12 when they van der Bass family penthouse turned back into the Bass Suite - he didn't move back - Bart craved the solitude as much as his son did. As said, Lily kept her guardianship over Charles so now that she didn't have Bart to fight with about the boy

"He should just be seen not heard!" Bart would always cry when they fought about him.

"Yes, but you can never see him!"

She ensured that he spend every weekend at her, Serena and Erik.

Over the years, Blair and Chuck grew closer and closer, they began to realise that they were in fact eachother's biggest Allie and source. Blair would find the victim - Chuck could plot some embarrassing situation and the pair would initiate. Us 100 the World 0.

Harold Waldorf along with Lily saw the potential - although Eleanor was not so enamoured. She'd always liked Nate, his name was old money and blood bound to royalty! And her Blair was born to be Royal. Yes, Nate was not so well socialized, his manners were appalling and his mother had about as much charisma as a beetle but the name, oh yes the name. Blair Archibald - that had a ring to it, there were no van der Bilts her age, Tripp was left-handed bow-legged, their children wouldn't stand a chance! Nate had strong arms and broad shoulders. Oh what beautiful Grandchildren she would have!


"My father was shot dead two summers ago," Chuck told Dan, "it was a mistake - he wasn't the target," he continued, "Bart was a bastard, my whole life, all I knew is that I was the reason that my Mother is dead, but that summer, something changed, maybe I did and he saw it I don't know..." he paused and took a breath, "I had begun working with him at Bass Industries, directly with him, he saw it as teaching me the ropes."

"What changed that year? What was different about you?" Dan probed, as the party was dying down he undid his tie, Chuck on the other hand was still impeccably dressed.

"Blair. I was different, better in fact, all because of her," he finger tips grazed his eye lids for a moment.

Serena wandered back over and sat down in the seat next to Dan, "I left a message with Dorota, I hope everything is okay,"

Chuck looked up at her, "I was going to marry her, Humphrey," he declared, "I love her unconditionally."

Serena smiled sadly at him, "What changed?" Dan asked.


March 1920

Howard Archibald had struggled with money since he left his military post, Anne had a taste for the finer things in life - she was a van der Bilt after all. He needed a plan.

Prohibition had come into action in January of that year, he'd struck on an idea with his brother-in-law William van der Bilt || - bootlegging. This whole thing wouldn't last long anyway. So for six weeks they make a few thousand dollars together.

Howard went to Bart Bass needing more money - they'd been friends for years! And Howie would play him back with interest! They just needed a little kick starting.

"Are you an idiot? I'm not putting my money into this, get out Howard," Bart scolded.

After a few weeks together, William van der Bilt ||| got wind of this and ordered the pair to stop immediately - the family does not need this sort of scandal nor does he want to bail the pair of them out. Howard always was greedy and got Bill (as he was affectionately) known to do one last heist.

It didn't go down well, Bill was shot by policemen and Howie was arrested and locked up. To keep the thing quiet, William ||| didn't bail him and cut off his daughter - no way was he keeping her afloat! He told her not the marry the bum.

Howard was livid - he was stuck in jail because van der Bilt didn't want the aggravation of bail. Anne was devastated - her best asset was now her son, all these years of grooming him into the perfect Mama's Boy would pay off, "We need to pull together - we need to make this work, Nathaniel," she told him.


"I can't remember the day my father died," Chuck told Daniel, as he scribbled down these notes, "We were on our way to the Bronx - he'd found a plot where the next hotel could be.." Chuck paused, "A car sped passed us and two men in suits shot him, only one hit him, but it was enough,"

Dan never thought he'd ever feel bad for Chuck Bass of all people, Dan couldn't imagine losing his own father - let alone witnessing it.

"I'm sorry, Chuck," Dan said softly.

Chuck waved his hand, "I need another favor from you," his eyes slit up to Serena, "the both of you actually,"

Serena and Dan nodded.

"I want you to set up a meeting, I just need her alone. No Nate, he'll distract her. Invite her to tea, whatever."

Serena bit her lip, "I don't think it's such a good idea, Chuck.."

"Sis, if I wanted your opinion I would have asked. Just give me this." Chuck was near begging.

"I'll set it up," Dan replied, he took Serena's hand, "We'll set it up,"


Just a note - thank you so much for the lovely, kind words. It's really inspired me.

Sorry this chapter is a bit jumpy in places - really needed to fit a lot into one so the ball can start rolling..

I hope you enjoyed.

*from Ferris Bueller..

**Of course from Gossip Girl.

Bx