August 24th, 1998

3:14 P.M.

As eight year-old Blair Cornelia Waldorf swayed back and forth on the swing in the park, looking the picture of perfection as her mother and a group of Upper East Side hostesses chatted a few feet away, Serena van der Woodsen was playing football with the boys.

"Serena, come on, pass it!" Nate Archibald cried out, his dark blonde hair unkempt and his boyish grin melting Blair's heart. Serena continued to run across the bright green lawn, giggling and holding the ratty old ball in her tiny hands like her life depended on it. Blair rolled her eyes and surveyed the scene, silently thanking God that she was nothing like her bubbly counterpart. What proper lady would roll in the mud and toss a dirty pigskin around? Her nice chocolate curls would've fallen straight and her shiny new Spectators would surely have scuffed from all that sprinting. No, she was completely content with watching on from afar, swinging, and feeling the wind in her hair.

As eight year-old Charles Bartholomew Bass sat on the wooden bench under the big oak tree, examining the black Zippo lighter he'd stolen from his father's desk, his best friend, Nathaniel was actually wasting his time trying to play along with that ditzy van der Woodsen girl. His sharp brown eyes looked towards the town car that patiently waited for the boys, when they were prepared to leave. He wasn't sure how long Nathaniel would fawn over the dazzling blonde, so Chuck stood and looked for something to amuse him, and brightened considerably upon seeing just the right person, that wouldn't fail to bring him entertainment. Blair.

"Why are you all by yourself, Waldorf? Don't want to get your shoes dirty?" He eyed her two-toned, patent lace-ups, figuring they were brand new. She simply stared at him with a fierce look in her eye. "Chuck," She ground out, as politely as she could, "could you please leave me alone? I just want to swing in peace, for once," Her voice was edgy and she averted her gaze, as if to silently end the conversation. Instead of doing as she asked, he took the swing to her right and began to watch her, adding to her frustration, as a smirk graced his features.

"Nathaniel has a thing for Serena, doesn't he?" He inquired, his tone feigning innocence, and glancing at her from the corner of his gaze.

Her expression hardened and she stared straight ahead. "Of course not, Bass. Why would you think that?" Blair would never admit what she was thinking; Nate didn't like Serena, because he had to like iher/i. Her mother had even said so - they were perfect together. They were going to get married someday. Serena was just his friend. To him, she was one of the boys. Just a beautiful, sparkling, Goddess-like boy. Of course. Chuck shrugged, knowing perfectly well that he was getting to her. He fell silent and let her stew in her thoughts, turning his head to eye the rest of the park, and feeling the waves of anxiousness roll off the little girl next to him as each second passed.

As Serena scored, Nate threw his head back and his hands up in surrender, laughing all the while and shouting something to her before jogging back to the swings with flushed cheeks and bright eyes. "All right, Chuck, let's go. I think I need to get home since we have school tomorrow. See you later, Blair," He waved and began to walk towards the black car parked on the curb. Chuck hopped off the swing and sent a devilish grin Blair's way, "Bye, Waldorf." He said, turning his back and following Nate, knowing that his words earlier had struck a chord.

Blair and Serena made their way home, Serena still wind-blown and breathless from her football game, and Blair still brooding and quiet. As her, her friend, and her mother made their way back to her Fifth Avenue apartment, her mind raced. Tomorrow was the first day back to school after the summer. She had to do something to make Nate see that Serena wasn't anyone compared to her. She was a princess, and Nate was her prince. No questions asked.

Staring at the window with large eyes, she watched yellow taxis and pure-bred dogs fly by outside. Her spirits were almost lifted, just by looking at the city before her. The Upper East Side -- her home -- was like the little spot of shining gold on a rusty piece of metal. The rest of New York didn't compare to the towering buildings, designer boutiques, manicured lawns, and historic land marks planted around this magical place. As the car pulled towards the apartments, and Serena flounced out onto the sidewalk in a flurry of blonde hair, she sighed and stepped out a bit more gracefully, her mind already plotting.

After Serena went home, and after she had dinner with her mother and father, she retired to her bedroom and stared at herself in the mirror. Then, she mechanically placed her new school uniform out across the chaise, brushed her teeth, said goodnight to Dorota, and settled into her bed, half dreading, half eagerly waiting for the next day at Constance Billiard.

---

August 25th, 2004

7:41 A.M

"Blair! Can you believe it? We're in high school," Serena's enthusiastic voice rang out through the hotel lobby as she dragged her friend out the doors and onto the Fifth Avenue sidewalk, smiling brightly.

Blair had to admit, her energy was contagious. She found herself grinning alongside her friend, "No more God awful plaid dresses," She said with relief in her voice, making Serena burst out laughing.

"Those things were so fucking ugly," She breathed out, looking over Blair for the first time and gasping, "and you look amazing! Wow, Blair, you went all out," She examined the darker-haired girl's attire - the required high-waisted, navy skirt and white button-up shirt, both ironed and crisp, along with stockings, Miu Miu flats, a bright purple Versace headband, under which settled a bundle of chocolate waves, and glossy ruby lips, which were now pulled into a pretty pout. "And... you didn't," Blair commented, immediately noticing, with distaste, Serena's wrinkled uniform, runs in her tights, unwashed hair, and the lack of makeup on her face.

"Yeah, stayed up way late last night. Me and Georgie went down to Brooklyn to see this band, and oh my God, Blair, the drummer was so adorable, I couldn't stop looking at him. He asked for my number and everything," Serena's babble had never interested Blair. If anything, it put her in a sour mood. Serena is only fourteen, Blair thought, the same age as me. While her best friend had been out slumming it in Brooklyn, she was holed up in her room picking out her clothes for the next day and looking at her cellphone, waiting for Nate to call. He never did.

"That's great, Serena." She muttered, not hiding the disdain in her voice, as they walked up the steps of Constance Billiard School for Girls, ignoring the students that were watching them with interest, noting each detail of their outfits, each expression across their face. They were It Girls. Proper celebrities. Well, at least in their high school they were.

Heading for the joint Constance-St. Jude's courtyard without hesitation, they made a beeline for Nate, who was already sitting with a group of his friends on an old stone table in the corner, looking positively impeccable in his uniform, but messily smoking a joint before his first class. As he passed it to Chuck Bass, who was eyeing the two approaching girl's with a look that only the typical teenage boy could produce, Nate turned.

"Hey, Serena, Blair." He nodded at the two, seemingly not as excited to be in ninth-grade as everyone else was. "Nate, look at you," Serena squealed, ruffling his hair, "You're a high schooler now!"

"Our Natie is growing up," Blair commented fondly, shoving Nate's shoulder gently and perching on the cold stone of the table, ignoring Chuck's gaze as he inhaled on the joint.

"Yeah, yeah, whatever. It's not any different than last year, right? Except the classes are a shitload harder." Nate grumbled, though a smile was evident on his face. "You're excited and you know it! Look at it this way - only four more years until college!" Serena, always the optimist, stating, her own smile blinding anyone who dared look her way.

The jealousy of Serena and Nate's 'unique' relationship had passed over Blair years ago, for the most part. Now, she knew they were just friends. Her and Nate were not officially together, but on her fourteenth birthday, he'd kissed her for the first time and left her beaming the rest of the night. Everything was perfect.

The smoke filled Chuck's lungs and he suppressed a cough, looking on at the trio. He didn't understand how Nate could be so close with the two girls without subtly suggesting a threesome to them, or at least a 'friends-with-benefits' situation. Although he had watched the strange love triangle unfold before him like a fly on the wall for almost all his life, he was still slightly unclear on where his friend stood. Last Thanksgiving, Nathaniel had told Chuck that he'd kissed Blair, and that he wanted to ask her out. But two months before that, he'd hinted to him that he had a thing for Serena. Whatever was going on between the three, he wanted to be a part of it. Or at least know all the recent news on the unfortunate, yet slightly charming, soap-opera-esque scene taking place right in front of his very eyes.

Although he wouldn't admit it, he almost felt bad for Blair. They never acted it in public, but she and Chuck had developed a strong bond over the years. He'd seen her cry countless times, listened to her despairing thoughts over the phone for a long time now. He never said a word to anyone about it, and uncharacteristically stored all her secrets in him like a safe, locked away and secured with high-tech alarms and lasers. Only the best for Blair Waldorf, of course.

He wouldn't say he had a soft spot for the girl, per se, but he could confess that he liked her much more than he liked Serena van der Woodsen. Sure, he wouldn't deny the blonde if she offered to crawl into bed with him, but he had no attachment to her annoyingly high-energy, lovable attitude, surprisingly.

The table chattered away until the bell rung, and the start of the Freshman year finally kicked in, after much waiting. Blair bounced to her first period expecting the worst and hoping for the best. Her number two pencil was sharpened, her new notebook free of eraser shavings, and her mind sharp. This would be easy.

---

June 13th, 2005

1:54 A.M

"Hello, New York! How are you doing on this fine night?" A familiar voice surfed over the cool air, above the sea of cars on the street and swirling into the barely-starry sky.

"Serena, shut up! You're wasted," Blair shoved her friend away from the open bay window, in a fit of laughter all the while. Every boy in the penthouse was staring at the leggy, bronzed blonde as she drunkenly fell on her ass and erupted into a fit of giggles. "Could someone pass the champagne? I'm a little parched," She sang out, clambering to stand upright again and sauntering towards the kitchen,

Blair had decided to have a small beginning-of-summer get together at her apartment. And it was small, for her standards. Only about twenty-five people strung out around the large space. And, like always, Serena had decided to drink as much as she could, and wear the most revealing dress she could find, just to make Nate stare at her the way that Blair had wished he wouldn't. That look in his eyes was reserved for his girlfriend. Her.

And now, Blair had to look after her trashed friend while Kati Farkas and Isabelle Coates jumped on her bed upstairs and Carter Baizen and three of his Senior friends smoked something suspicious on her mother's expensive leather couch. "Serena? Maybe you should check in for the night. Come on, let's go. You can sleep over here and stay in the guest room, okay?" She finally began to drag the drunk girl away from the champagne bottle and up the stairs, despite protests. "Blair, lighten up! I'm not tired," Serena mewled, as she was forced against her will away from the party. But the moment she was pushed onto the bed, she suddenly realized just how exhausted she was. "Okay, I take that back." She mumbled, as Blair tucked her in like a child.

"And if I so much as see you two feet out of your bed, you're going to get it," Blair snapped, turning the light off. "'Night, Serena, see you tomorrow,"

"Night, Blair. Love you." Her best friend murmured under the covers, laying awake only a few minutes before slipping off to sleep.

Seven weeks later, Serena left for boarding school without so much as a goodbye or an explanation.

---

October 23rd, 2007

12:28 A.M

"God, do you ever get tired?" Blair inquired with slight exasperation as she felt his lips nip at her collarbone once again.

"Of you? Never," He replied quietly, his hand gliding down her side and tugging slightly at the hem of her night gown. "I'm flattered, really," She said, her words trailing off as his tongue ran up her neck. "Come on, Waldorf, cut me some slack," His voice was uncharacteristically desperate as she half-heartedly attempted to push him away. The only light in his hotel room was the brightness of the T.V. screen, the volume turned down low.

He could hear her breathing and practically feel her smirk, "Why should I?" She questioned, a delicate hand coming forward to tangle itself in his hair, a rare act of tenderness.

"Because I'm letting you spend the night in my suite," He murmured against her skin, and she let out a breath of laughter. "Like that's such an accomplishment. I'm sure I'm not the first, Bass," Despite her words, she pulled him towards her and brought her lips to his, before pushing slightly and winding up straddling him. Looking down towards his handsome face, she set to work and began to pull at his boxers, earning a smug grin from him.

"A little eager there, don't you think?" His own hands were glissading across her shoulders and pushing the restraining straps of her loungewear down, and she scowled lightly, kissing him yet again.

Minutes later, she was rocking against him and purring his name as his breath hitched as they finished breathlessly. Leaning forward, she sighed contentedly and didn't say a word for quite some time.

"I thought you were going to last longer than that," She finally noted after a moment of silence, flashing him a grin and sliding away, off the bed. "I was going easy on you." He shot back, watching her glide into the bathroom and running a hand through his hair. He heard the sink begin to run and suddenly wished that tomorrow she wouldn't leave him for another day. Maybe, if they were different, she could call in sick from school and lay in bed with him all day, watching old movies until the sun sank.

But that would never be them, because he had better things to do than look after her, and she had better people to see than Chuck Bass.

As she slipped back under the covers with him, he wondered when this was going to end.

---

February 1st, 2014

4:01 A.M

"Just make them get me the fucking epidural, Chuck," She practically shrieked, gripping the handles of the hospital bed and letting out a labored breath. "You sure you don't want to just stick it out and do this thing au natural?" His voice was extremely easy-going -- much too calm for Blair's liking.

"Don't play with me right now, let's just try to get through this, okay?" She snapped, shooting him a death glare as he turned to speak to the doctor about doping her up with had promised herself that she would have at least one child by the time she was twenty-seven, but she was not expecting that child to be Chuck Bass' as well as hers. It still shocked her, sometimes, when she really thought about it.

Sure, she loved him. He loved her. They were having a baby together and maybe one day they'd actually get married, officially. Who knew? All that was clear was that they were happy with eachother and she had tamed him; something that no one thought was possible. He'd settled down with her, he'd made the ultimate commitment, and that was good enough in her eyes.

Her mother wasn't in the hospital room with her (business trip, of course). Her father wasn't able to fly out from Paris on such short notice. Serena was in Mexico with her newest 'serious' boyfriend, and Chuck was the only one at her side as the doctors instructed her rather rudely to push as hard as she could.

It was a boy. Seven pounds, four ounces, with a head of dark brown hair. She fell in love with him the moment she laid eye on his little face, and all she wanted to do was hold him close. Ivan Charles Waldorf-Bass. It was perfect for him, fit him like a glove.

Chuck watched silently as she cradled her baby in her arms and stared down at him, taking in every detail. "They grow up fast, so I want to memorize what he looks like now." She said softly, a small smile playing at her lips. "Or we could just take a picture," He commented, smirking at her, though there was a gentleness in his gaze, and she rolled her eyes at him. She supposed some things never changed, and for that, she was grateful.