I just re-watched the episode in Season 5 where Blair told Chuck she wasn't in love with him and where Ivy got all of the money. It was the most ridiculous episode of Gossip Girl I've ever watched. Instead of getting angry I actually laughed. This is a funny one-shot that I wrote to express my feelings on that episode. It might be a little unrealistic but quite frankly, I don't care. Let's presume that Chuck didn't speak to Lily just yet about Jack saving him.
Serena was sitting downstairs on the lounge in the lobby of the Van der Woodsen apartment. This day couldn't get more messed up. With the drama of Ivy, Lola, Carol, her Grandmothers crazy Irish wake, the outrageous reading of CeCe's will, her own best friend having feelings for the love of her life, and Georgina's looming presence, Serena didn't know how she hadn't had a drop to drink today.
Serena rubbed the temples of her head as though she had a headache from the many thoughts swirling around in her head.
Oh God. That was so something her mother would do. Now things were really getting out of control.
Chuck was on his way down the elevator thinking about the conversation he had just had. So Blair apparently wasn't in love with him right now.
Well, that sucked.
Especially since he was going to raise a family with her not too long ago. He had even messed up his pattern of mature behaviour and everything over the past two weeks just to get through to her and clear his own name.
What a waste of time that was. Blair was somehow too enraptured by the wool-haired Dan to think of anything else.
Chuck walked out into the lobby to find Serena sitting there with a pinched look on her face. He repressed a chuckle, and sat down to join her.
"Hey" Serena said when she noticed him, unable to stop herself from giggling a little. She didn't know why. Maybe it was because Chuck was the only person who could actually empathize with her today.
"Hey" Chuck replied simply with a smirk.
"What a shitty day" Serena said in a matter-of-fact tone. She wasn't usually the swearing kind, but what the hell. She had a God damn shitty day today.
"Mm" Chuck murmured simply, before pulling out a flask of scotch from inside his jacket and taking a sip. Serena watched him with a tired smile and held her hand out. Chuck gave it to her wordlessly and watched in amusement as she drank it thirstily.
"Mind if I join you?" Georgina drawled, taking a seat on one of the couches.
"Why are you even asking Georgina? You know you're going to join us anyway, like really" Serena exclaimed, rolling her eyes. Georgina had to chuckle, and shrugged.
"Humour me" she said, and motioned for the flask. Serena just sighed and handed it to her.
"What are you drinking for?" Chuck asked, in a dull tone, slouching in his chair. He almost looked like his junior year self for a moment, just bored with everything around him.
"I'm celebrating. I took down all of you today. What a mess" Georgina said with a huge smile, holding the flask out to toast herself before taking a graceful sip. Chuck and Serena just sighed exasperatedly and shook their heads.
"I miss take-downs" Chuck said softly, almost jutting his lip out in a pout.
"What are you talking about? Didn't you take down Dan today?" Serena asked with a laugh, happy to distract herself with this strange situation that she, Georgina and Chuck were in.
"Yeah..." Chuck drew out in a non-committal tone, "but it wasn't my best work. Georgina orchestrated most of it. Last week's Humphrey take-down was better."
"What did you do last week?" Georgina asked with a wicked grin.
"I..." Chuck said with a pause, flattening his mouth into a straight line as thought he was trying to suppress a laugh, and choking out the rest of the sentence "completely sabotaged his new work by sleeping with his assistant. I gathered enough information from her to manipulate things and make him look like a plagiarist. I even gave her a shahtoosh scarf as an extra touch."
Serena gasped and clasped her hand to her mouth. Georgina cackled immediately, applauding him.
"Chuck!" Serena cried, hitting him lightly, but a smile was creeping onto her face.
"I know, I know. It was very immature and not what the new Chuck should be doing" Chuck said playfully, shrugging his shoulders with a sheepish grin.
"But just imagine his face when he saw the scarf on her" Georgina said, and that was it. They all burst into uncontrollable laughter.
"I rea-lly sh-shouldn't be laughing but-" Serena tried to say between her giggles.
"Why not? Just laugh, you deserve it today" Chuck said with smile.
Serena paused as though she was considering it, then slapped her forehead and started laughing as though she remembered something else.
"My Grandmother's wake was an Irish theme" Serena said giggling, and they laughed with her.
"I actually befriended Dan Humphrey, and looked after him when he was drunk...and somehow he screwed me over and got my girl" Chuck said in complete awe and disbelief that they could all only laugh. It was just ridiculous.
From then on, they were just stating all the crazy things that had happened to them recently and laughing, forgetting what was appropriate and inappropriate.
"My aunt paid an actress to pretend to be our cousin Charlie and con us all" Serena spluttered.
"I accompanied her to the wake and destroyed nearly all of the attendees lives" Georgina said between her cackles of laughter.
"My grandmother left everything to the con-artist, everything" Serena said, clutching her stomach as she doubled over with laughter.
"Blair Waldorf is going to be poor" Georgina said, and though Serena and Chuck felt sorry for Blair, the thought of the materialistic princess having no money was so tragic it was hilarious. Plus they were a little tipsy.
"I made Blair Waldorf poor" Chuck said, his laughter dying down as he started to feel guilty.
"Please, there wouldn't have been anything to send if she wasn't kissing Dan while married to a Prince" Georgina said, rolling her eyes.
"The loves of our lives love each other" Serena said softly, shaking her head in disbelief. Chuck bit his lip and bounced his head in a nod. They sat silently for a moment.
"What is it about him? You've both also fallen for him at some point. I don't get it" Chuck asked, studying them and rubbing his chin.
"He..." Georgina sighed, going uncharacteristically serious all of a sudden, "makes you feel like you're something more, that you have a chance to not be so screwed up all time."
"Special" Serena said with a sad smile.
"But unlike our friend Serena here, I enjoy being screwed up" Georgina said with a smirk. They shook their heads at her as tiny, leftover titters escaped their mouths.
"I think I build up Dan to be this good guy that I can count on to be there for me any time, but maybe it's not the case anymore" Serena said sadly.
Chuck scoffed and Serena looked up at him.
"What?" She asked, narrowing her eyes slightly.
"Nothing, it's just funny how the tables have turned" Chuck said.
"What do you mean?"
"Didn't you once say that Dan put you on a pedestal? This time it's you who has built up an image of Dan to fall in love with."
Serena blanched as she thought about this. It did make sense, but she knew that Dan was actually a good guy when it came down to it.
"Dan has always tried to do the right thing, as much as it hurts me to see him trail after my best friend" Serena sighed, trying the mature approach like she did at the hospital.
This time Georgina scoffed.
"Have you seen Gossip Girl today? You are aware that the guy allowed Blair to believe it was you or Chuck who sent the video in at Blair's wedding, right?" Georgina drawled with a sneer. Judging by Serena's shocked and upset face, she hadn't.
"He's not the good guy from Brooklyn. Trust me, I've known longer than anyone what he's capable of" Chuck said in a dark tone.
"What has he done to you?" Serena asked in a small voice, almost afraid to know. Chuck paused hesitantly, because telling them this would make him vulnerable. He took another huge gulp of the flask of scotch.
"Nate doesn't know this, but in senior year I hung out with Dan for two nights when Nate was away" Chuck said slowly, as though he was revealing that he had cheated on Nate with someone else.
Georgina and Serena giggled, but sobered up at his serious expression.
"He came over, and asked to experience the world of Chuck Bass."
"That sounds supremely gay" Georgina quirked.
"Believe me, I asked if he was" Chuck said with a snort, "but anyway, I agreed to hang out with him, because Blair had said some things that day that made me curious about Dan Humphrey. The second night we hung out, we got into a bar fight and we ended up in a jail cell. He actually had my back..."
Serena's face brightened at hearing that.
"But I quickly realized it was so he could stab me in it" Chuck finished, and Serena's face fell.
"What did he do?" Georgina asked, now extremely curious about how Dan Humphrey had pulled a number on Chuck Bass.
Chuck sighed, and took another sip of scotch as he steeled himself.
"We talked about fathers, mainly my father. I told him about my mother and how my father hated me for killing her. Moments later, I found notes that proved that he had been writing a story about me. For a second there, I trusted Dan Humphrey with the darkest secret I held at the time, and you know what happens when I trust someone...I realized that the brief moment of friendship was all for an ulterior motive." Chuck said in is raspy voice, staring straight ahead.
Serena didn't speak, and she just stared in disbelief. Georgina was now very intrigued by Dan's hidden dark side. It could prove very useful in her future vendettas.
"Chuck," Serena said softly with a sigh, trying to find the right words to say.
"It doesn't matter anyway because I got past that. I didn't get angry when he wrote in Inside that I would end up dead hanging in a closet. In fact, I helped him to embrace the success he was receiving with Inside. I tried to get him to stop procrastinating and actually tried to help him to move forward," Chuck explained.
"Like almost a substitute for Vanessa" Georgina said with a smirk.
"I guess in a way that's true" Chuck said with a chuckle, "and he helped me too by introducing me to Monkey and stopping me from spiraling downwards again. We actually had a real friendship, and in a way we were keeping each other company while we were barred from Blair's heart, even bonding over the Matrix. At least that was what I thought."
"And the truth was?" Serena asked, dreading Chuck's answer.
"Humphrey once told me that I was kind of like a brother, and as embarrassing as this is, I agreed. Which meant that I expected him to not be hiding things from me about Blair and why she shut me out of her life. It was something serious this time, not high school drama, because Blair was going to be my family before the accident. I warned him to tell me the truth. Then the fiasco wedding happened and all of the truth came out. Before I knew it, Dan Humphrey had betrayed me again" Chuck finished with the coldest look that his glazed over, tipsy looking eyes could manage.
It was silent for a moment.
"I'm sorry Chuck" Serena said. She couldn't think of anything else to say, but she now knew that whatever relapse in good behavior Chuck had made through his revenge on Dan was well warranted. Who actually cared? Dan had been a total jerk in this situation and deserved what Chuck did to him.
"So Humphrey had a plan all along? I have a whole new respect for him" Georgina said in an impressed tone, slurring slightly as the scotch got to her.
"The funny thing is, he confessed it to Blair right now in front of me. But somehow she still wanted to be with him" Chuck said in a bewildered tone, laughing in shock, and it began again. Chuck, Serena and Georgina's combined laughter at how ridiculous everything that was happening was.
"Blair told me that her friendship with me was way more important than her relationship with Dan, but when I was sitting outside of the hospital room where my Grandmother was dying, she confidently kissed Dan right in front of me" Serena said, in an equally bewildered tone and laughed disbelievingly, "like seriously, what the hell is that?"
"Wh-what?" Chuck choked out between his laughs.
"I understand the concept of retribution for you sleeping with Nate all those years ago, but even I think that was a bit much" Georgina exclaimed, sputtering with giggles.
"I know, right? And it's not like Nate was the love of Blair's life in the end. We all know that it's Chuck" Serena said, rolling her eyes with a smile at her brother.
"Maybe" Chuck said with a small smile.
"Enough talking about love" Georgina said in a bored tone, "what's the deal with everyone's sex lives?"
"I haven't slept with anyone since Ben" Serena slurred carelessly because of all the alcohol, and chugging down another sip of the flask in front of them as though the thought actually depressed her for a moment.
"I cut down on the sex too as part of trying to be mature, but I'm still Chuck Bass. I just don't have one-night stands to try and numb my pain or as a personal vendetta. Well, except for my brief affair with Alessandra the other week. Nothing too wild," Chuck murmured, taking a sip of the scotch as well.
"I've been too busy scheming to have sex, and my husband bores me" Georgina sighed, "ugh, here we are, possibly the 3 wildest of all the Upper East Siders back in the day and our sex lives are tame to non-existent."
Chuck and Serena couldn't help but smile for old times' sake.
"I could call my coke-dealer and have a fun night, if you're interested" Georgina said, as usual taking it too far. Chuck and Serena glanced at each other for a moment, before looking at the psycho sitting with them as though they had just realized who they had been hanging out with.
"Definitely not drunk enough for that" Chuck mumbled, standing up and packing away his flask.
"Oh come on, don't you remember the last time we partied together Chuck?" Georgina asked with a smirk. Chuck's eyes actually widened in fear as he stared at the girl who took his virginity. Serena didn't even bother to ask, afraid to know what Georgina had done to make the great Chuck Bass call someone else a psycho.
Serena giggled instead, and stood up to wrap an arm around her brother, almost stumbling in her drunken state.
"You know who Georgie would get along with? Your uncle Jack" Serena said, and Georgina's eyebrow raised in curiosity.
"Don't even suggest it" Chuck said in a snappish, warning tone at the thought of the most messed up people he knew getting together.
That would be when things really got strange.
There you have it folks. I'm not a Dan-hater and I am a Derena fan. I'm just a person who loved the Dan and Chuck friendship that was starting to happen and was disappointed when it didn't work out. They were more entertaining than most of the dynamics on the show, and they actually helped each other to move forward without holding the other back, not DAIR. It happened in Season 2 and 5, and both times Dan was the traitor who ruined everything. Grrr. I'm also a die-hard Chair fan, so I wasn't too pleased with the direction the episode that this fic was based on went.
If you think about it, Dair really fucked up everything. I mean what role did Dan and Blair's relationship have in the end of Gossip Girl? It contributed nothing to the main concept of the show. Like it was absolutely useless, especially considering the fact that Gossip Girl began because of Dan's obsession with SERENA. What was the honest point of actually making it look like Blair had fallen in deep love with Dan in Season 5? Why wasn't it made more obvious that she was running away from Chuck? They forever tainted Chair and Derena through writing Dair.
And also, Dair was written so terribly, in the sense that one minute all the characters could tell that Dan loved Blair, and the next minute someone was shocked to discover that he loved Blair. I can cite several examples of this:
1. In 5x02, Chuck said to Dan "Did that hurt? Wish I could feel it" when he told Dan that he was the last person Blair was with before Louis. So we get the impression that Chuck knows of Dan's feelings for Blair. But wait, a few episodes later, in 5x08 Chuck apparently "just realized" with a shock that Dan was in love with Blair, and that's why Dan was so upset about Serena not inviting him to the bridal shower.
2. When Dan's book came out, Blair yelled out "There is no us, all there is is friendship, and even that's gone now." So wasn't that Blair revealing that she could acknowledge Dan had feelings for her? Nope, she still thought his motives were only friendly for the rest of the season up until him kissing her on Valentines day. Makes total sense doesn't it.
3. Serena gave the impression of knowing that Dan was in love with Blair and got really jealous over it several times before 5x10. But she still seemed surprised when she said "You mean...you were going to tell her you love her?" in 5x10.
So what exactly was going on? It made no sense. Did people know about Dan loving Blair or did they not? It was the weirdest and messiest storyline. It was all over the place and they had to make up something like Dan going to an essay contest for Blair years ago to make Blair going for him seem logical (Newsflash: it didn't). It was confusing and weird. The writers should actually plan seasons better instead of making huge random jumps like that. Sorry but that was the extreme downfall of Season 5. Other than that, Season 5 was actually one of my favorite seasons.
There's my rant and my fic, I'd love to know your thoughts and if you agree through a review or a private message.
Thanks :)
