Disclaimer: Gossip Girl's characters and plots, both from the TV show and the books aren't mine!
Based off Season 1 of the TV show, here is Chuck's perspective on his life, Blair and everything that has happened. Please R&R!
The Very First Time
The very first time Chuck Bass has ever remembered his father, the infamous Bartholomew Bass, congratulating him, smiling add saying he was "happy for him" was exactly 12 hours and 3 minutes ago. Of course, right after dear old father said that, a lecture reminding him not to screw anything up, this time, followed.
That was typical.
And very-much expected.
He had once told a certain someone, a special someone, when he wanted to buy Victrola that his father was his toughest critic, and ironically, it was that special someone who he had just spoken to his father about.
You see, the very first and only time Chuck Bass fell in love was approximately eleven years ago; the very first time he met Blair Cornelia Waldorf.
Of course, at that age, he was too young to realize what love was, so he did what any other young boys supposedly in love did. He pulled her hair. That had raised a hell of a reaction from her. The attention he enjoyed immensely, and only encouraged him to continue on.
Eventually, he realized, that his behaviour meant she now despised him. Yes, she used at the oh-so-tiny age of seven the word despise, (which he didn't understand and had to ask his nanny secretly when he got home what it meant) to describe to him just exactly how she felt about him. So by then, he decided, he needed another tactic of getting her attention. Therefore Nate came into the picture.
Chuck had to admit though, that was a very grave mistake he made on his part, one which he only had to suffer through for the next 6 years and 4 months. Or was it longer? He didn't like to keep track.
At the age of 12, he wasn't the only one who believed themselves to be in love, Nate Archibald had admitted and declared very publicly that he was in love with Blair, and had asked for her hand. To go on a date, of course. Chuck assumed naively that Blair only agreed due to the large amount of audience this spectacle attracted. And for the first time in his life, he was wrong.
So from that second on, he, Chuck, was the pacifier between the on-again, off-again couple. The one who chose the birthday, Christmas and Valentine's presents, the one who reminded the boyfriend of dates and anniversaries completely forgotten, the shoulder of support for Blair to cry on each time, and the one, who unwillingly, helped them get back together. Chuck never said he suffered through those years because he had no choice, he simply did not want to see the girl of his affections hurt. He told himself it was because he preferred calm, rational girls, and couldn't deal with tears, but secretly it was because he never minded Blair Waldorf in his arms, holding on to him ever so tightly for support and comfort.
As time passed by, Chuck came to hate the loneliness in his heart, and looked elsewhere for a solution. So, he lost his virginity, very regretfully too, to that, ugh, Georgina when he was thirteen. He had sex with an endless string of girls; blondes, redheads, Chinese girls, Caucasians, girls with big boobs, girls with no boobs, girls that offered everything, girls that had nothing. And when he was clear enough to know what he was doing, he stayed away from brunettes. That didn't mean they stayed away from him. They even came to him in his dreams, and with all those girls, his sole purpose of using them was to get rid of the image of Blair Waldorf.
Obviously, it didn't work.
Finding another excuse, Chuck told himself that women aren't worth it, he didn't need to respect them, because they never respected him, or really, one of them never respected his feelings. It was just a way, his way being bitter. However, he couldn't bring himself to disrespect Blair.
Time passed, and there came the point where he had believed they had really broken up. Well, maybe he wasn't wrong to believe that. He was just so surprised that she didn't go running back to him again immediately, that she said she felt relief. It was the night that changed his life.
No exaggerations there.
It was the very first time, he allowed himself to be in love. And this time, he knew how it felt. Despite the number of women he slept with, none had ever gave him the feelings he had felt with Blair. Just watching her on stage was enough. And then...she kissed him. Hell, he even asked her if she was sure. The look that she gave him, the way their noses touched just before their lips met, sent shivers down his spine. Sometimes, he still can't believe she was the one that moved towards him, that she was the one who kissed him first. He might just say he had fireworks and move on with it, but it was impossible to describe anyways...the way she grabbed him closer, the way they touched, the way it felt when they were together.
Finally together.
To think, the day after was her birthday. That was the very first time that Chuck Bass had been nervous with a girl. He had never confessed before about having "butterflies,' and he was only hurt in the process. Of course, he responded in the usual Chuck Bass way. He never meant to hurt her with the bet, but sometimes she was just so stubborn. The worst part was that she almost cried in public.
No one knew better than Bass that a Waldorf never cries in public.
He hated it when she was sad, when she was angry at the whole world, and he hated it more when she hated herself above all. He had meant it when he said something this beautiful deserves to be seen on someone worth its beauty, for she was truly beautiful. Later, he realized that, she wasn't upset that they had broken up, she was upset because everyone had found out, on the day of her birthday. She as upset because Nate was with someone already, meaning that she never really mattered to him. Chuck knew she hated feeling inferior. It was worth spending a fortune for her, to make her happy.
It was worth it for him too.
Love had never been so enjoyable when it was a secret. Once they had gotten over the "guilt." He loved their trysts, the coded texts but it was all ruined, because Nate wanted to get back together with her and he knew she would say yes. The debutante, the plot with Carter, it had been all useless, and stupid. He was extremely jealous when she agreed to go to the cotillion with him, but he was also Chuck Bass, and Chuck Bass did not get jealous. In the aftermath, she ran back to Nate. It was the very first time Chuck felt heartbroken, over a girl, a relationship, his feelings, his situation. It didn't lasted long, and wouldn't happen again, he made sure of it.
It was a grave, costly mistake.
It became a period in his life that he doesn't want to talk about.
He had lost his best friend, the girl he loved, and worse, his heart. And when she came back to him, he despised himself so much, he said whatever he could to hurt her. He wished Blair had slapped him, wished she had done anything except walk away.
For a while, everything in his life was just blank. Repetitive, meaningless periods of struggling to continue onwards. And thankfully, although he shouldn't say it, Serena brought them back again. Maybe he should thank Georgina, that psycho bitch too. It was a time for them to forgive and forget, and come together once again. And getting back, working with Blair had never made him happier. Especially that sexy smile she had given him when she approached him with news of Georgina. For the very first time in a long time, he smiled.
He had missed the feeling of being beside her, and was to his heart content when he found himself awake in her arms, her snuggling closer to him. Of course, he only pretended to sleep so she would slap him awake. It had been worth the slap too. To be very honest, he had never been so proud of someone as the day when Blair brought Georgina down. She had been downright a bitch, and a vicious one two. He loved her for it. He had never been so proud of how gorgeous she was at his father's dreaded wedding. The pink pattern dress and that pink matching headband made his heart jump, and she had looked so innocent and beautiful. How very true and contradicting. But there was Blair Waldorf for you, a blend of all the things in life you desire and despise.
Reconciling with Nate just made everything a lot better. And...getting Nate's approval almost. So he had made his father happy, for the very first time, and he had took a plunge, risking it all, and said what he meant from his heart.
"One thing I learned, in the face of true love, you don't just give up, even if the object of your affection is begging you to."
That had to be the biggest life lesson he learned. And with it came the greatest of rewards.
"You never belonged to Nate, never will."
"You don't belong to anyone."
And then he kissed her. It wasn't rushed, hurried or desperate. Instead, he kissed her slowly, tenderly and lovingly. Through his lips and that kiss, he told her how happy he was, how undeserving he was of this and his longing for it. That night was the first night chuck agree it wasn't sex, no matter how good it was, it was making love. He remembered waking up in the morning and simply lay there, enjoying the petite brunette resting in his arms. Chuck had never been so grateful for anything until now. He traced her eyes, her nose, her lips, and felt himself question his actions. He was truly... different around her. She blinked a couple of times and smiled when she found him looked at her. She hit him gently and he laughed.
A true, Chuck-Bass-was-happy laugh.
So when he approached his father to announce the news, his father's first reaction had been surprise. And denial. Then came the questions. Chuck had to grin at himself at the realization too. In truth, he wasn't even sure. Their relationship had begun once again, the night of the fateful wedding.
His father had been a bitch about it, warning him, and Chuck rebelled.
Naturally.
It took a while for his mind to make sense again, and after apologizing profusely to a very confused and somewhat pissed off Amelia, he ran after Blair, well not technically. He knew he couldn't have made it to the helicopter, so instead rushed to meet her at the private jet. And bought a bouquet of bigger, better roses along the way as well. She had met him with a surprised and happy smile, and he felt relief and happiness swell in him too.
Chuck Bass had just saved his ass from perhaps, the biggest mistake he could have made in his life.
In all his years, he had never met someone who could be themselves around his father. But at the next famous luncheon one of their prestigious families held, he turned and saw his girlfriend, (god, he loved using that word for her) talking animatedly to Bart Bass. There was no sign of awkwardness, no body indication she was trying to find an excuse and run away. Instead, she even looked like she was into the conversation.
Curious, he walked over, placing a hand gently on Blair's back. His father was smiling.
"Blair here, was telling me about your latest accomplishment in starting another club like Victrola, without any financial help at all. I heard it's as much as a success as it was the original. It seems Charles, you're more like me then I thought."
Chuck smiled grimly, "I try to hide it."
"Like father, like son, always the modest one." Blair laughed, looking up at him with delightful eyes. Bart smiled again.
"You remind me of Lily." He said in a tone which seemed to be approvingly. Chuck couldn't help but grin, if anyone apart from his 'step-mom' can make his father smile twice in a minute, then they were really something.
Of course, Blair Waldorf was never an exception.
It was like the first time he said I love you. Hell, after talking to his dear stepsister about it, which involved him patiently waiting for her to finish recalling the first time brooklyn boy had said it to her, he had even felt more nervous. What would her reaction be? Maybe she'd stand there like Serena and just say "okay." Or maybe she'd laugh in his face. This was Blair he was talking about here, capable of anything. He even decided asking Nate, but backed out last minute, thinking how much a wuss he was, even going far enough to ask the ex-boyfriend for help?
And Chuck Bass was no wuss.
Determined to do it right, he called her out, told her to dress nicely, (when wasn't she dressed nicely?), and to be ready at seven. He had planned to tell her after desert, when they were sitting there, enjoying the champagne, laughing, smiling, like those famous movie scenes she loved, and then, the music would change, he'd look her in the eyes, say the magical words and then kiss her.
Of course, it never happened.
Because she wanted to do something new, risk-taking and something she'd never done before. He swore she was insane, or had been badly influenced by some romantic idea, when she told him what she wanted. But he wanted her happy. So after thinking quickly, he took her to the beach on Long Island, fed her the classic fish n' chips with his fingers and they sat there, "cuddling," watching the sunset together. He watched her, amazed, playing in the waves, getting her very expensive Versace dress wet and not caring about it at all. He didn't even protest as she pulled him into the freezing cold water. At that moment, she was so...beautiful, so natural, so free. And he said it. Without any thought or hesitation at all.
"I love you."
She stopped. Looking at him with great big brown eyes, she bit her lip, not managing to hide her very please smile and embarrassment at the same time.
"What did you say?"
He said it again, figuring it was too late to back out.
"Chuck Bass, never did I think, there'd be a day, when those three most romantic words would leave your mouth."
He smirked at that.
"And to say it to you at that. So?"
"So?"
She splashed him playfully and ran off, chased after her, catching up easily, and lifted her up. She shrieked, pretending to protest.
"Well from what I heard, doesn't the person receiving it reply or something?"
"Really?"
He grinned evilly, and began tickling her, the weakness she had that he only knew.
"Okay, okay, I love you too!"
He put her down and smirked.
"Thought so."
She giggled, still breathless, and he kissed her. Blair never explained to Dorota why her very expensive, unique, custom-made dress was covered in sand afterwards.
And so, as their relationship developed, Chuck found himself putting more effort into it than he ever imagined. Of course, he wasn't complaining. But it got tiresome, the anniversaries, the social events, the presents for Christmas, birthday, Valentine's day, etc. etc. etc. But he vowed never to forget any of it, because she would have been pissed and he loved her too much to stop.
The first time they got into a fight, a serious one too, not the usual squabbles and quarrels, they didn't talk for a week. By then, rumors on Gossip Girl had already spread that they had broken up. It was expectant.
After a couple of days, Chuck couldn't even remember what the fight was about, but he held on to his pride, and refused to move. It drove Serena and Nate nuts trying to talk some sense into the both of them, stubborn and arrogant, the two refused to back down or apologize. He had felt horrible, lonely and quite possibly even guilty, but they eventually came to a compromise. Knowing Blair, she probably even rehearsed it. The two had stood there facing each, both awkward, and stuttering for words. So Chuck made the first move, and kissed her. She kissed him back. And no words needed to be said after that. Chuck Bass would admit he has had a lot of sex before, sex in unimaginable locations, different positions, with a variety of girls, but never has he experienced make-up sex. Which made it all the better.
Heck, he would be willing to get into more fights if this was the outcome.
After her fateful graduation at Yale, and his, surprisingly, to everyone including himself, at Oxford, Chuck Bass made one of the most important decision of his life. He decided to take over his father's business. Bart Bass was hesitant at first, but decided it was high-time he retired and handed the keys of the Bass empire, not to mention the bank account, to his finally trustworthy son. At the celebratory dinner, organized by the lovely perfectionist, his girlfriend herself, he stood up and proposed a toast.
"I've learnt a lot of things since the last time I proposed a toast, I've learnt through experiences as a man to admit wrong...even if he isn't, (laughter and a smirk from Blair), I've learnt to be responsible and respectable, to handle business and contracts. But most importantly, I've learnt how to sustain a cherished relationship, (sighs and aws) I've learnt the power of perseverance and of trust, and most importantly, how to love. For all of you who read gossip girl, (more laughter), you would all know who I'm talking about here. To Blair Waldorf, the most important person in my life, (he raised his glass in recognition and she smiled, touched. There was a nervous pause and then he smirked), Blair, I love you. Will you marry me?"
Silence.
Serena gaped, her hand covering her mouth in shock and disbelief. Dan beside her smiled, gently taking her hand away and kissing the wedding ring on her finger. Waiting anxiously, Chuck was unaware of Nate's encouraging and approving nod, his father's beam and the pleasant smile of everyone around.
Blair Waldorf couldn't believe what she had just heard. She, never, ever had imagined this moment. Sure, she dreamt of an extravagant wedding ever since she was little, and planned out exactly how Nate was going to propose, but that was before Chuck. With him, everything was so...unpredictable, so wild and so different from her perfectly controlled life. So before she knew she was doing, she had stood up from her seat, rushed over and kissed him.
The room sighed.
"I take that as a yes?"
"Yes." Blair replied breathless. And Chuck slipped a ring on her finger.
"It's...Chuck...you...ohmygod..."
Those were words enough. He smiled at her reaction, relieved.
"You deserve the best." And before he could kiss her again, the others had already cutted in.
"Hold up your hand, darling. Let mother get a good clear look."
"WOW! B!"
"Oh! Let me see!"
Serena, Jenny, Eleanor, and even Lily had run over to examine the precious stone. Exasperated, Chuck stood off to the side, waiting for the admiration to end, so he could claim back his, fiancée. And that was when his father came over.
"Congratulations son, looks like, I was wrong. You really are like me, started as one who had nothing and did nothing except fool around, but now, you clearly have everything. I'm proud, and happy for you. She's a wonderful girl, she does you good."
"She's everything I have, dad."
"Then hold on to it. You're a lucky man, Charles. Don't lose it now."
And with a clap on the back, he was gone. Nate was next.
"Who knew there'd be a day, when it was like this."
"Our roles switched."
"And you do a better job at it then I did. Sadly."
"Now, now Nathaniel, I've said it to Blair before, she doesn't belong to you. She's mine."
"Relax man, with the size of that rock on her finger, there's no way I'm going to be able to steal her back from you."
"I can't believe you said that."
"Chuck, I'm joking. Besides, look at how happy she is."
"Amazing. The press will have a field day." Dan said, joining in, and handing another glass of champagne to the each of them. The three of them looked towards Blair, she was glowing, and that mere sparkle the ring gave off, just added to it; a finishing touch. "Chuck Bass, the womanizer, settling down?"
"Now that's hard to believe." His two best friends chimed together, and then Chuck grinned.
"Cheers."