Author's Note: Hey, people! So, basically this fanfic is five times Chuck told Blair he loved her, as you read in the summary, so yeah. I hope you guys like it! Read and review por favor! Oh, and special thanks to the amazing Michelle (sunday nights), for letting me know what she thought of this and for giving me the title! Now on with the story. :)

Disclaimer: If I owned Gossip Girl, there would so not be a month long hiatus.

A five-year-old Blair Waldorf sat on a bench at the Park Avenue Presbyterian playground smoothing out imaginary wrinkles in her bleach white dress. She had a plum colored satin bow tied around it, and a white patent leather headband placed amongst her flawless chocolate curls as she sat and watched Nate and Serena play on the swings.

It wasn't fair. Why did Nate like Serena better than her? She had a theory that it was just because Serena's hair was blonde and shiny.

She grabbed her purple pea coat off of the bench and wrapped it around her shoulders as the cold October air began to blow harder, sending chills up and down her tiny spine.

She glared ominously as Nate pushed Serena higher, her best friend giggling in response. Blair pondered whether or not she should tell Serena she liked Nate. Maybe that would get her to stop playing with him so much.

As she continued to ponder her predicament, she heard footsteps approaching behind her and whirled around to see none other than Chuck Bass standing before her.

He was wearing a little white suit paired with a purple dress shirt and a white tie.

"Waldorf," he smirked, sitting down next to her.

"Chuck. Always a pleasure. Oh, wait, no, it's not," she retorted.

"Okay, what's wrong with you? Just tell me because you know I'll find out," he demanded.

Blair's response was to motion with her tiny hands to Nate and Serena playing on the swings.

"Are you kidding me?" Chuck scoffed, raising an eyebrow at Blair, which simply earned him a withering glare.

"Why would I be kidding?" Blair returned.

"Nathaniel may be my friend, but he's excruciatingly dull," Chuck drawled.

"You sound like you're forty. Where did you even learn the word excucatingly?" Blair mispronounced.

"You said it wrong. And that's not the point. If you really want Nate's attention there's only one thing to do," Chuck informed her.

"What?" Blair probed.

"Make him jealous," Chuck suggested with a smirk.

"How would I do that?" Blair asked, eyeing him suspiciously.

"Easy. Pretend I'm your boyfriend," Chuck told her.

"Ew, no!" Blair scoffed, a disgusted looking gracing her features.

"Well, if you really want Nate to like Serena…" Chuck hinted.

"Fine," Blair huffed, "What do we do?"

"Easy, just ignore him and act like you like me. Just pretend I'm Nate," Chuck explained.

"Fine," Blair gave in, "But this better work, Bass."

"It will," Chuck promised, "Now give me your hand."

"Ew, why?" Blair wrinkled her nose.

"Just do it," Chuck insisted, rolling his eyes as Blair grasped his hand.

The two began to walk toward Nate and Serena, a smirk on Chuck's face while Blair tried to stay calm.

She really hoped this idea would work.

"Hi, Serena. Hi, Nate," Blair greeted.

"Hi," Serena enthusiastically replied with a huge grin.

"Hi, Blair," Nate smiled.

"What are you doing?" Serena asked her friend.

"I'm just playing with my boyfriend," Blair boasted, showing off their entwined hands to Nate and Serena.

"Chuck's your boyfriend?" Nate incredulously inquired.

Blair nodded in response, pressing her small pink lips against Chuck's cheek.

Blech. She was going to have to take a shower after this.

Chuck grinned from ear to ear. Blair Cornelia Waldorf had just kissed him. He felt a slight fluttering in his stomach, but chose to ignore it and give his attention to the situation at hand.

"Come on, Blair, let's go play on the slide," Chuck insisted.

"Okay," Blair grinned happily as she skipped off with Chuck.

"That was disgusting," she declared as soon as Serena and Nate were out of earshot, wiping her mouth off several times using the sleeve of her coat.

"You're telling me," Chuck lied.

The two walked in silence until they reached the large slide. After they had gone down it a few times, Chuck saw Nate approaching in the distance and informed Blair.

"Nathaniel's coming," he declared as she reached the bottom of the slide.

"What do we do? Act like you're my boyfriend!" Blair commanded.

Chuck looked at Nate's approaching figure, which was coming closer and close to the slide, sans Serena. He examined Blair, who eyed him expectantly. His tiny heart was beating faster and faster as he looked between the two and finally he did the only thing he could think of.

He pressed his lips against hers, in a short kiss, his pulse racing a mile a minute as he felt the nervous fluttering return to his stomach.

Out of the corner of his eye, Chuck could see Nate watching them, an annoyed expression gracing his boyish features.

If Blair wanted him to act like her boyfriend, then he would.

"I love you," Chuck informed her.

"Nate," Blair greeted, turning her attention to the blonde-haired boy standing beside them, "What do you want?"

"I love you more than Chuck. Will you be my girlfriend instead?" Nate asked.

"But what about Serena?" Blair inquired.

"I like you more," he grinned, flashing his bleach white teeth.

"Sure!" Blair happily grinned, tossing her arms around Nate, "Can you give me a minute to break up with Chuck first?"

"Sure," Nate agreed, "I'll be waiting by the monkey bars."

As soon as Nate was gone, Blair unleashed her wrath on Chuck.

"How dare you!" she shouted, kicking him forcefully with her brand new Mary Janes.

"What did I do wrong? You're Nate's girlfriend, aren't you?" Chuck retorted.

"You stole my first kiss!" Blair hollered angrily.

"What do you mean? You kissed me first!" Chuck defended.

"On the cheek! It's different," Blair pouted, "I wanted my first real kiss to be with Nate and now it won't be! It's all your fault!"

"Well, how was I supposed to know?" Chuck grumbled, feeling a pang of an unnamed emotion that he would later categorize as jealousy wash over his body.

"Look, let's just pretend it never happened, okay?" she insisted.

"Fine," Chuck agreed, "Get back to your boyfriend."

"Will do," she smirked in response, sauntering off toward the monkey bars leaving Chuck alone.

A/N: Well, I hope you enjoyed this! I know they seem really mature for kindergarteners, but I tried, I really did! Well, anyway, you know the drill. Press the pretty button!