The Unlikely Couple

Disclaimer: Everything belongs to Gossip Girl

No one expected Chuck and Serena to get together.

If someone had asked Chuck Bass one year ago what he thought of Serena, he would have smirked and drawled that Little Miss Sunshine was a little too Mother Teresa for his taste. Serena Van der Woodsen, if asked the same question, would have shuddered and said that even if Chuck Bass was the last man on earth and for the sake of mankind's existence she had to procreate with him, she would prefer to live a solitary existence in a cave.

However, everything changed in senior year.

Chuck idly regarded the flecks of gold that reflected off the whisky as he swirled a glass under the lamplight before consuming it and savouring the fluid sensation that ebbed down his throat leisurely.

"At the Scotch again, Chuck?" came a soft voice from his doorway.

Chuck's head shot up and saw the slim figure of his stepsister Serena leaning against the doorway with her long gold hair cascading down her shoulders like a silky vale.

"A gentleman must have a hobby," Chuck drawled, raising his glass to Serena in a mock toast.

"I would hardly call you a gentleman, Chuck."

Chuck laughed humourlessly. "That is the general consensus amongst our dear Upper East Siders."

Serena stepped into his room and gracefully perched herself on the edge of his bed, her blue eyes appraising him.

"If I was more sober, Van der Woodsen—or should I say Bass, considering we're now officially step-brother and sister—I would proposition you in a shameless manner followed by mind-blowing sex on my bed. But since I'm completely intoxicated, I'm going to be impossibly virtuous and ask what's with the sisterly concern tonight?"

The corners of her lips twitched and Chuck wasn't sure if she was fighting back a smile or a grimace.

"Chuck, I know you're upset about Blair and Nate getting back together, but drinking is not going to help you deal with the situation. I of all people should know that."

Chuck snorted derisively.

Serena edged closer to him and pulled the Scotch bottle from his grasp. "I'm serious, Chuck. No one is worth tearing your liver to shreds with booze."

Chuck did not bother fighting to reclaim his Scotch. Feeling defeated, he flopped back down on the bed, staring up at the ceiling. His eyes widened in surprise when Serena lay down beside him, tucking her hands behind her head and crossing her ankles together. The two lay side-by-side in silence for an indeterminate amount of time.

"Your bed's surprisingly comfortable," Serena said, breaking the silence.

"So I've been told," Chuck replied, a touch of his old smugness creeping back into his voice.

"Eww, Chuck."

A smile almost flittered across his face and then it faded, as he thought of Blair who had been the last one to share his bed—and if the truth be told, the only one he wanted to share his bed for the rest of his life. But it was not to be. Her white knight, Nathaniel-fucking-Archibald, swooped in on his great white charger horse and swept her off his feet with a Tiffany's diamond bracelet and spouting words of eternal devotion and love that sounded as if he had ripped it off from Sir Walter Scott or Elizabeth Browning.

"You know there are other people in the world besides Blair. You're in high school and there will be, God forbid, another woman who will love you and all your—uh, attributes."

"How comforting."

"Chuck."

Chuck sighed. "I really thought Blair was the one. It sounds absolutely pathetic but I really thought that I would be married to Blair one day. She understood me and could match me in everything."

"Wow…Chuck, I-I…wow. I never knew you felt that strongly about her."

"Van der Woodsen speechless. That's something you don't see every day."

Serena rolled her eyes and the mattress moved as she turned on her side so that she was facing Chuck. Her blue eyes were full of compassion. "I never thought I'd say this…but I'm really sorry that things didn't work out the way you wanted to."

Chuck shrugged. "Blair and I weren't like you and Brooklyn Boy. You two are the stuff of fucking fairytales. You're the blond princess and he's your bloody Lancelot."

"You not only have feelings but you're also learned in Celtic mythology."

"Don't push it, Van der Woodsen."

Serena smirked and in one fluid movement, got off the bed. As she headed to the door, Chuck said, "Van der Woodsen?"

She turned to face him. "I'm not going to have sympathy sex with you."

For the first time in three weeks, Chuck grinned, albeit mockingly. "I would never dare to go that low. I do have some morals, you know."

Chuck saw with some satisfaction that Serena was fighting to keep a straight face.

"What I wanted to say," Chuck continued, "was thanks."

"Did I just hear Chuck Bass say thank-you?"

"If you tell anyone, I shall have to kill you."

Serena laughed. "Your secret is safe with me."

Four weeks later, Chuck was about to watch Donald Trump's The Apprentice, when he heard a low sob come from the bathroom. At first he thought it was the Botox-ridden lady on the floor below who cried daily into her bottle of tequila and sleeping pill cocktail, but when another sob erupted that was distinctly louder and definitively came from the bathroom, Chuck, feeling charitable, got off the Italian leather couch and gently pulled open the door.

There was Serena in a foetal position by the sink, crying.

Serena looked up, mascara running down her cheeks and her hair wet with her tears. "Go away, Chuck," she choked.

"Charming," Chuck replied, sitting down beside her and casually leaning back against the marble and gold plated sink.

"Leave me alone!"

Chuck didn't respond. Instead, he reached up, grabbed the tissue box and silently handed her a tissue.

Something indiscernible flashed across Serena's face and she accepted the tissue without further comment and blew her nose in a rather unattractive fashion. Seemingly without his own volition, Chuck found himself reaching over to her and pulling her damp hair off her face into a messy twist with a hair tie that was lying lonesomely on the tiles. Something between a choked laugh and a sob came from Serena at Chuck's actions.

"Thanks," she hiccupped.

"Anytime. You know that I don't like seeing my step-sister looking like she's been dragged behind a tractor for three weeks."

Serena blew her nose again and Chuck could have sworn that a sliver of a smile appeared on her face.

"Dan cheated on me with Vanessa!" Serena suddenly blurted out and turned her large Pacific Ocean eyes to Chuck, who found himself momentarily struck by the plain anguish that shone in them.

"Brooklyn Boy cheated on you with Wal-Mart Wanker?"

"Yes. Apparently he's in love with her."

"What's wrong with that fuckwit? He's got you—the golden haired toast of New York, yet he goes for a girl who appears as if she's raided the nearest charity shop. Are you sure Brooklyn Boy wasn't high on something when he broke things off with you?"

"I wish."

"Would you like me to do something wonderfully underhand to him? Make his life hell? Get him expelled? Post some malicious lie on Gossip Girl and then—"

"No! No! Don't do anything of the sort."

"Geez! Take a horse tranquilizer, Van der Woodsen. I won't do anything unless you ask me to…though I kinda miss the Pre-Boarding School Serena who would not have hesitated doing that kind of thing."

"If I was Pre-Boarding School Serena, I would most likely be drunk up to my eyeballs and unable to form any coherent speech."

"And all the boys who like to take advantage of inebriated girls are still mourning that fact."

"You're disgusting."

"And proud of it."

Chuck tipped his head on the side appraisingly. "Are you sure there's nothing I can do for you?"

"I don't feel in the mood for amorous activities, Chuck."

"Get your head out of the gutter, Van der Woodsen. I was actually being genuinely sincere."

Serena's eyes softened. "Who would have thought things have come to this? You and I in a bathroom together just talking together. In my perfect world, I'd still be with Dan and you'd be with Blair."

"It's a fucked up world, Van der Woodsen."

Serena lightly touched his arm. "Actually…I'm not sure whether it's just post-break up trauma, but its nice sitting here with you."

"You must have severe post-break up trauma to say that. If it's any consolation, you can do so much better than Brooklyn Boy. I wouldn't waste a minute longer on a guy who chooses Brooklyn trash over you."

"It must be a fucked up world, Chuck, if you of all people are giving me relationship advice."

Chuck smirked. "I have hidden depths."

Serena rolled her eyes, but she was smiling and Chuck realised that he had probably never seen a more beautiful sight. Her cheeks were streaked with mascara, her eyes were puffy and her hair was damp, but she was smiling, and Chuck knew that she was going to survive. And somehow by looking at her, Chuck felt that he could regain his life again and find some semblance of normality.


After that night, awkwardness settled over Chuck and Serena. They felt as if they were balancing on the edge of some new unknown territory and they had no idea on what to do. Should they retain the old enmity and sniping? Or should they move forward and be civil? Unconsciously, the pair decided to settle in the middle of the two extremes and alternated from treating each other as if they were diseases to lying comfortably on the couch sharing a bottle of Scotch or a box of Belgium chocolates whilst watching DVDs.

Lily Bass watched the new developments with some relief, thinking that at last, the Bass-Van der Woodsen family was going to meld and behave like any other normal family. Eric, on the other hand, was apprehensive and trusted Chuck about as much as he would with a man holding a machete and mustard gas. Bart was indifferent and merely nodded banally whenever Lily mentioned the subject.

At Serena's behest, Chuck even started to socialise with Blair and Nate again. Though, Chuck said that Serena always had to accompany him because he did not want to be the third wheel and watch Blair and Nate practically suck each other's faces off. Serena agreed to Chuck's conditions, because she felt, oddly enough, a need to protect him.


September rolled around and it was the annual Costume Ball for charity. This year, it was chaired by Lily, much to Serena's chagrin, as her mother made her run various errands and hang around the ballroom bored out of her mind at the tedious arrangements ("Do you think gold and silver would send the wrong message?" "Do you think chicken salad is a bit too cheap looking?" etc. etc.) And at the end of each long day, Chuck would always be lounging lazily by the bar and hand her a martini and for some perverse reason that Serena refused to contemplate, she actually looked forward to these moments they spent together.
Blair had helped Serena pick out her costume (to be honest, Blair took complete control and Serena merely nodded obediently as Blair thrust the purchases into her hands) and insisted that she come over to the Penthouse so the both of them could get ready together for the ball.

"Are you sure you want to come over, because Chuck is going to be there." Serena asked as they rode the elevator to the suite the Van der Woodsen-Bass family shared.

"I really don't care. Bass and I are past history. I'm with Nate now," Blair said haughtily, though Serena could detect a forced casualness in Blair's demeanour.

The elevator slid open with a 'bing' and the girls entered the apartment.

"Well, well, Waldorf. Welcome to our humble abode. I'm surprised Nathaniel let you off his tight leash," Chuck drawled, taking a swig of champagne.

"It's a bit early for drinking, isn't it, Bass?" Blair snapped.

"Just getting warmed up for the party, princess."

"Would you two cut it out?" Serena said exasperatedly as she practically manhandled Blair to her room.

"I'm surprised you even can stay in the same room with that sexual predator," Blair said in a deliberately loud voice that Chuck was obviously meant to hear.

"I didn't hear you complaining six months ago, Waldorf!" Chuck called from the other room.

Blair slammed Serena's door shut in response.

"You two are so immature," Serena said. "Ignore him and let's get ready for tonight."

While the two girls were getting ready, the doorbell rang again. Chuck swung open the door and was surprised to see Nathaniel standing awkwardly there.

"Don't worry about Waldorf, Nathaniel. Her virtue is being assiduously guarded by Serena."

"Chuck, don't be an ass," Nate said tetchily.

It was only then that Chuck realised what Nate was dressed as and Chuck could not restrain a smirk. Nate was dressed as a Tudor courtier, complete with pantaloons, tights and jewelled doublet and a cap with a floppy feather.

"Don't. Say. A. Word," Nate warned, flushing a deep red. "It wasn't my choice."

"Waldorf's eh?"

Nate nodded sourly and Chuck shooed him in.

"What are you going dressed as?" Nate asked, accepting a Scotch from Chuck and downing it quickly.

"James Bond."

"Figures."

"At least my costume doesn't include shiny white tights and a campy feather on my hat," Chuck smugly replied.

"Fill up my glass again," Nate commanded.

"Can't face the ball sober?"

"Shut up. Just give me another drink."

Chuck grinned and complied with Nate's request.

Almost two hours later, the girls emerged from the bathroom and Chuck nearly choked on his martini when he saw Serena. She was…he could not think of a single adjective that would do her justice…even the word beautiful seemed trite.

Serena was dressed as a Grecian goddess. Her hair was pulled off her neck in a messy bun with curly strands falling gracefully around her face. She shone with bronzed glitter and a serpentine gold bracelet with diamonds was wound around her upper arm. Her slim figure was swathed in a brilliant white one-shoulder gown that clung to her upper body then flared out at the hips so it appeared that she was bathed in white mist. Her make-up was simple, in bronze and champagne colours with a dash of coral-coloured lip gloss.

Chuck slyly glanced out the corner of his eye at Nate who appeared just as dumbstruck and riveted by Serena.

"I'm sure Brooklyn Boy will get the shock of his life when he sees what he's missing out on," Chuck said appreciatively.

Serena smiled winningly at him and Chuck was surprised to see a faint blush staining her cheeks. Was Serena actually blushing at his compliment? Chuck thought incredulously. He couldn't restrain himself from staring at her and from all appearances, neither could she.

A loud, indignant cough severed their eye contact. It was Blair who had come into the room after Serena.

"So what do you think, Nate?" Blair asked, twirling around, pouting.

"L-l-looks beautiful, Blair," Nate stammered.

Chuck realised as he watched Blair who was dressed as a medieval princess in a blood red gown and decked out diamonds, that for the first time he did not feel a pang of regret nor did he feel jealousy when Blair covertly eyed him as she lingeringly kissed Nate.

And when he glanced again at Serena who ducked her head when she met his gaze, he knew why.

The ball passed in a blur for Chuck. He observed with some malign satisfaction the priceless look on Brooklyn Boy's face when Serena descended the stairs behind Lily and Bart. He disregarded Blair's attempts to make him jealous. He chatted pleasantly enough with Nate when Blair was not hanging off Nate. He flirted shamelessly with Kati and Isabel and every other nameless girl that crossed him. And in between all of that, he sought Serena through the crowd and when he spotted her, she would turn to face him as if the two of them were pulled together by some magnet and they would share an intense gaze before they'd both turn away and continue whatever they were doing like they were strangers to each other.


Chuck shrugged out of his Armani dinner jacket and tossed it carelessly on his desk chair. The party was still raging downstairs but he had had enough and wanted to get away from the stifling atmosphere. Normally he would be down there partying hard until the early hours of the morning but tonight he was not in the mood for it.

He tiredly went to his mini bar and poured himself a Moet champagne as someone (most likely his 'dear' dad) had swiped all the good stuff and then kicked back on the couch.

Not long after, the door creaked open and Serena entered. The two then held unwavering eye contact for an indeterminate amount of time and Chuck resisted the urge to just kiss her senseless and feel her warm limbs wrapped around him.

"Got sick of showing off to Fuckwit Humphreys?" Chuck finally asked, breaking the tension.

Serena sighed. "Something like that."

"Moet?"

"I'll drink it from the bottle."

"Classy," Chuck dryly commented, raising an eyebrow but not questioning her as he passed her the bottle and she took a great gulp.

"Vanessa looked gorgeous," Serena said bleakly, kicking off her Jimmy Choo strappy heels and flopping down beside him on the couch.

"You've got to be joking. Her gown was hideous and her eye make-up left a lot to be desired."

"You're just being nice."

"Me being nice?"

Serena's lips twitched. "Good point."

The two sat in silence for sometime and Chuck stiffened but then relaxed as he felt Serena rest her head on his shoulder. He tentatively brushed her hand with his and was pleased when she encased his hand within hers, revelling in this close contact. Chuck twisted around so that he was facing her. "You looked hot tonight, Van der Woodsen. In fact more than hot—incredibly and mind blowingly gorgeous," he said softly, his spare hand stroking her hair.

A shiver ran through him as he felt her warm lips pressing against his throat. "I haven't been able to stop thinking about you all night," she breathed.

"Me neither."

"Everything's changed so much. You…me…"

"I know, I know," Chuck said hoarsely, his eyes lingering on her full lips.

"Chuck…" Serena whispered, leaning in so painfully close to him.

The almost breathless plea in her voice broke his self control and he kissed her hard. Her body was ready for it, and when he pinned her down underneath him, she struggled softly, but in a way that showed she didn't want to win, as she arched her body against his and ran her hands down his back and then under his shirt, feeling his warm, bare skin. A low groan escaped his throat as he pulled her hands behind his head and her fingers weaved tightly into his hair. They gripped hard, and he bit her lip in return, causing her to moan softly and arch her body shamelessly against him.


Blair impatiently waited for the elevator door to open, annoyed that Serena hadn't replied to any of her text messages. She had seen Serena go up earlier but didn't follow her as she had assumed that she was going to freshen up but after one hour, Blair decided to check up on her, hoping that she wasn't crying over that loser Humphrey and that Brooklyn bitch Vanessa.

She cautiously opened the door to the apartment so as not to startle Serena but no one was in the living room. She could hear a low murmur and then some rustling from the direction of Serena's room. She soundlessly pushed open the door and her breath stopped in her throat when she saw her leggy best friend entwined with her ex-sometime-boyfriend Chuck. A breathy sigh from Serena shook Blair from her numbed state and she quickly left the pair, her stomach twisting and it was only when she left the apartment that she was assailed by the irony of the situation: Serena had found Blair in exactly the same position two years ago at her seventeenth birthday and now…Blair wanted to be ill and was filled with what she refused to identify as jealousy.

I hope you all enjoyed it! This will be a 2-parter and the 2nd part will be posted in the next week or so. Please review and tell me what you think!