Summary: "No matter what we do and how much we fight, it'll always pull us in" - Blair Waldorf. Once soulmates meet, their destiny together is inevitable. A collection of one-shots featuring Chuck and Blair's unforgettable story of becoming friends and falling in love from their childhood days, to their high school days, and to their married life.

Setting: Kindergarten

Disclaimer: Gossip Girl characters don't belong to me. Lyrics belong to Colbie Caillat

A/N: Thank you everyone who left a review. They were super encouraging and I'm really glad you guys liked it :) Thanks to everyone also for subscribing, favoriting, and following this! You guys are the BEST!


What if we were made for each other
Born to become best friends and lovers
I want to stay right here
In this moment with you
Over and over and over again
What if this could be a real love
A love, a love, yeah

~What If by Colbie Caillat

Blair sighed contentedly while nibbling away on the mini macaroons Dorota had packed for her snack time. By the first week of kindergarten, Blair had chosen some of the top kids in kindergarten to be in her group. Nate and Chuck were both very handsome boys and Chuck dressed in what her mother would approvingly call "high fashion." Serena was likewise a pretty girl with nice, long blonde hair. At first, Blair did not want a girl prettier than her in her group as she liked to be the best in all areas. However, she could not help befriending the girl who had hugged her and kissed the top of her head when she got a mud stain on her new dress.

On the very first day of school, one girl had "accidentally" dropped a mud ball she was holding onto Blair's dress. Blair tried her very best to hold back her tears but the thought of the stain on the dress her mother had made for her first day was too upsetting.

As she cried, a beautiful girl with loose blonde locks behind her tapped her shoulder and asked her what was wrong.

"My dress," sobbed Blair, "It's dirty and my mom made it just for me."

Blair was soon engulfed by kisses on her head and warm hugs from Serena, who kept on telling her that it was okay and the dirt would come off. From Serena's affectionate comforting, Blair no longer cared how much prettier Serena was than herself. She quite liked how Serena made her feel better and took care of her even though they didn't even know each other that well. (On Serena's behalf, Serena later told Blair that she couldn't bear seeing such a cute girl looking so devastated on their first day of kindergarten).

Now all four of them were sitting at a snack table together, swapping and trading their snacks while chatting animatedly about the limo Chuck said his dad was going to buy him.

Their conversation halted when Serena interrupted to point someone out.

"Why does that girl keep on staring at us?" asked Serena confusedly.

"Which one?" asked Nate, looking around.

Serena pointed her finger at a girl with dark hair looking haughtily at them, "That one!"

When the all of their heads turned to look at this girl, she quickly turned back around.

"Hey! That's the girl who got mud on my dress!" cried Blair as she recognized the mean girl.

"That's her?" exclaimed Serena. Blair nodded.

"Why did she do that to you?" asked Nate, surprised. He was still innocent to how female minds worked.

"Georgina Sparks?" asked Chuck.

"How do you know her name?" questioned Blair.

Chuck lowered his head and whispered to his table, "I heard the teacher call her name when she got in trouble for spilling orange juice on Keith on purpose."

They all turned to look at her again, this time more closely, before turning back.

"We should stay away from her," said Nate.

The rest nodded their heads in agreement.


School had ended half an hour ago and Blair was still at school. She sat outside by herself on the steps, hugging her knees ashamedly. Of all things to happen to her in kindergarten, getting in trouble was never on her list. Yet, this afternoon, Blair had spent a long, thirty minutes with her teacher after school while all the other kids went home. All because of Georgina Sparks.

It was free-time for them, a time when the teacher let them do whatever they wanted in class. Blair was at the art station, drawing a picture of her and her new friends. She was just coloring in Chuck's dark blue suit when her artwork was suddenly snatched away from her by Georgina.
Georgina, who was standing right behind Blair, furrowed her eyebrows as she looked at Blair's picture.

"Hey! Give that back! That's mine!" protested Blair angrily, her hands on her hips.

Georgina looked at the angry girl and smirked," What are you going to do if I don't?"

Blair huffed, "If you don't…I'll…I"ll…"

"You'll what?" teased Georgina, still holding up Blair's work away from her reach.

Blair spotted Georgina holding her own drawing in her other hand and immediately grabbed it.

"I'll color on this!" said Blair. And with that, she scribbled furiously with a black crayon all over Georgina's drawing.

Blair was just about to give Georgina a smirk in return when Georgina threw back Blair's paper and cried for the teacher.

"Mrs. Reynolds! Blair drew all over my paper!"

The teacher came over to quickly resolve the dispute.

"Blair, why did you do this?" asked the teacher.

"She stole my paper first!" protested Blair.

Georgina denied this. "I didn't do that! Blair's just angry because mine looks better than hers!"

"Yours does not! You draw your heads so ugly!" retorted Blair. It was true. Georgina drew her people with a square head while Blair had actually taken the time to draw oval-shaped heads for her friends.

Mrs. Reynolds sighed. All she knew was that Blair drew on Georgina's paper which was not something she condoned.

"Blair, I'm going to have to punish you," told Mrs. Reynolds.

Blair looked at her teacher, horrified. "But…but…"

"No 'buts'. You're going to have to stay after school with me for thirty minutes and help me clean up the classroom."

Thinking about what her mother would say when she found out, Blair hardly noticed Chuck standing behind her the entire time.

Chuck lingered behind her, unsure of how to approach her. He rarely felt sorry for other but there was something about Blair. Chuck didn't like seeing the girl with beautiful brown curls and bright eyes look so upset. He thought she looked the best when she was happy.

"Are you going home soon?" asked Chuck as he sat down next to her.

Blair turned towards the boy's voice, saw it was Chuck, and asked, "What are you still doing here, Chuck?"

Chuck shrugged. "I think my nanny forgot about me."

Blair's eyes widened at how Chuck didn't seem to care about being left at school. "Why would she forget about you?"

"She's new…," explained Chuck. "She's always at the bar."

Chuck was used to incompetent nannies. No matter how much his father paid them, his nannies were always forgetting about him. The old ones couldn't remember Chuck's schedule and the young nannies were quickly distracted by the glamorous scene on the lower floor of the hotel.

"Oh, that's horrible," commented Blair. "Dorota would never forget about me."

Chuck shrugged again before changing the topic. "So do you want to get Georgina in trouble?"

Chuck's typical source of comfort after getting in trouble was to get the person in trouble in return (this usually applied to his nannies). To his relief, Blair was on the same page as him and was keen on revenge.

"Of course!" responded Blair.

"What do you want to do?" asked Chuck.

Blair paused at his question. Although she really wanted to get Georgina in trouble in return, she hadn't actually thought about doing so.

"I can dump paint over her head during free time," suggested Blair.

Chuck shook his head at the idea. "You would get in trouble again. We can't let the teacher see."

Blair thought harder while Chuck offered some of his own ideas. Within the next five minutes, the two children were enthusiastically brainstorming ideas to bring down Georgina Sparks. They were so engrossed that they hadn't even realized when Dorota finally arrived.

"Miss Blair! Dorota is here!" called Dorota, beckoning her to come.

Blair stood up, ready to leave when an idea popped into her head.

"Let's come up with more plans at my house! I'll tell Dorota that we're doing a school project!" said Blair excitedly.

The idea seemed very fun to Chuck and plus, he would rather be with a friend than be alone at home like he usually was.

"Yeah, let's do it!" answered Chuck, getting up and following Blair to Dorota.

Blair walked up to Dorota and explained, "Chuck's coming over to do school work."

Dorota consented, oblivious to the fact that kindergarteners did not have much school work much less work that required partners.

Thus began the history of the two infamous Upper East Siders who would later become well-known for their devious scheming and conspiring.


As soon as they got to Blair's penthouse apartment, they threw their backpacks and jackets on the sofa and resumed their plotting in her bedroom.

They came up with a few crazy ideas and some that were quite heinous for children their age to even think of.

"You can cut her hair during nap time when the teacher's not looking," proposed Chuck.

"Or mix paint and glue and put it in macaroons and then give her some during snack time," said Blair mischievously.

While eating the sweet delicacies Dorota brought up for them, they laughed over Georgina's possible reactions and made up some nasty nicknames for Georgina.

Despite a bad day at school, Blair found herself enjoying immensely coming up with ways to get Georgina in trouble. She also liked working with Chuck, who came up with some creative ideas himself. He didn't have a problem with making fun of Georgina either. All in all, it was by far the most fun Blair had in a while since kindergarten started.

However, all the planning was making Blair tired as well. She let a yawn escape from her mouth and tried not to close her eyes and take a long nap…

Chuck was in the middle of explaining an idea when he saw Blair closing her eyes and falling asleep on her bed. Her head was at the foot at the bed but that was only so she could talk to Chuck more easily. He stood up from the floor where he was sitting and observed her closer. She was indeed sound asleep.

Looking at Blair sleeping, Chuck began to feel tired himself. He looked at the floor and immediately decided he preferred sleeping on the bed. Anyways, Blair would be lonely sleeping by herself and she needed some company, Chuck told himself.

Chuck quietly climbed on her bed and slowly lied down next to Blair, trying not to wake her up with his movements. As he lied down next to her, he thought Blair was cold when she shivered slightly and moved closer to Blair. Finally feeling comfortable, Chuck closed his eyes with a certain girl's perfectly done curls and bright red hair-band as the last thought on his mind…


Dorota opened the door, ready to call Mr. Chuck and Miss Blair down to dinner when she was surprised by the sight of the two little children sleeping right next to each other on Miss Blair's bed. The two were facing each other with Mr. Chuck's arm draped around Miss Blair's waist. Dorota quietly closed the door and walked back downstairs. She didn't have the heart to wake up the two children who looked so innocent and perfect resting next to each other.


A/N: Well, well, isn't this Chuck and Blair in their natural element? Scheming & plotting at their finest. And Georgina Sparks...I guess it's true when they say childhood show us the essence of ourselves. ;)

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Thanks for reading & much love,

skyblueinkpen