As I'm such most of you expected, this is a big chapter. The thing that frustrated me about this one though, was that I try to follow canonical events, so with this storyline I had to take some scenes and conversations directly from the show. What bothers me about this, is that I want to give you guys something that you haven't seen (or read) before, but when it comes to keeping this story close to what happened on the show, sometimes I can't. But hopefully, I'm able to show you guys the things you've already seen with a new spin on it.
One other thing, something is brought up in this chapter that I thought was so important about the way Dan feels towards a certain character, and I hate that it was never addressed on the show, so I tried to acknowledge that, but move on quickly as well to keep the pace going.
"I have to admit, I didn't expect to have you back in my office so soon. You finished the rewrites quickly."
"Well, when you told me to go back and rework the chapters as a serial, it all fell into place quite quickly." Dan responded to his mentor.
"And it does work better." Shapiro agreed, nodding along as he looked back over the pages before him. "I especially like the introduction of the Charlie Trout character, he really brings a sinister element to the narrative."
"Yeah, I'd say sinister is the right word." Dan reiterated, shifting uncomfortably in his chair.
"This romance with Claire, that would really hook readers, I think you should explore it further." Shapiro added, his finger ominously running over the rim of his glass full of gin.
"Umm….okay." Dan sighed. "So, how do you want me to do that?"
"Keep doing what you're doing, except maybe now….why don't you try and push Blair towards her Charlie Trout?"
"What? You want me to interfere? I thought the point of all this is that I observe and don't interfere, like a cameraman filming a lion documentary." Dan began to ramble, then added, "and in this scenario, Blair is actually the helpless gazelle for once. I know that you like how…complicated and complex-ridden her life is, but she's a person and I really don't think that Chuck Bass is right for her."
"Humphrey, since you started taking my advice do you think that your writing has improved?" Shapiro's tone changed to a more commanding one, the one that Dan knew meant he didn't have a choice about this.
"Yes." Dan apprehensively admitted.
"Then trust me on this. All you're going to do is…encourage them to come together, whatever happens once they do would have happened with or without your input."
Dan swallowed nervously, but there was no real decision here for him to make. The more time and effort he put into this project, the further he was willing to go to complete it. And so the challenge was accepted.
Dan didn't really feel like it would be difficult to push Chuck and Blair together, as things between them seemed inevitable anyway, but he knew that Shapiro would be expecting a Claire/Charlie heavy chapter in a few days, so he needed to find a way to speed up whatever was going to happen to them.
He'd been working on the Claire Carlyle project for other two months now and had honed his skills of compartmentalizing. He could go to school, and be at home, and hang out with Serena and not think or worry about what he was going to write next. Then Serena would mention something about Blair, or Blair would join them for a minute because she needed Serena for a scheme, or to simply chastise her for spending too much time with him, and Dan would store these moments in his head for later when he came to writing the next chapter. He'd been getting along well with Serena this time, he was worried that he might fall for her again (which everyone else thought and would often tell him) and would be distracted from his work, but they seemed to be genuinely becoming friends.
This didn't make him feel as guilty as it should have done. It was that compartmentalizing expertise that was coming in handy for him, he could rationalize what he was doing and separate his actions from his morals when convenient.
So he sat with Serena when they ran into each other at lunch, he asked her how she did on his English essay, and she beamed about her A, then she asked about how Jenny was doing at Eleanor's and he responded that Jenny was doing great, though he didn't like the make-up she'd been wearing recently. Then Serena mentioned how Blair had been driving her crazy with this new game she'd been playing with Chuck.
"What is it this time?" Dan asked with a sigh, feigning sympathy with Serena's frustration.
"Oh, I'm sure you don't want to hear the details, but Chuck won't sleep with Blair until she tells him that she loves him." Serena said with a dramatic roll of her eyes.
"Serena!" Blair's high-pitched voice sounded behind them and they both jumped. "Why are you telling Humphrey about that?"
"Blair, come one, Dan's a guy maybe he could help." Serena remained calm while Blair stayed dramatic and gave Dan an intense stare, commanding him to prove Serena either right or wrong.
"Yes, if you're plotting against Chuck Bass, I'm sure I can think of something." He offered, and Blair accepted, joining them at the table.
"I was thinking I'd just disappear for a while and give him a taste of life without me." Blair launched straight into scheming mode.
"No, no, that's a terrible idea. Don't disappear, become…unavoidable. Chuck may be a deviant, but he's still a man, so just drive him crazy, wear him down. You should be good at that." Dan explained, Serena then gave Blair a triumphant look because she was right and Blair herself looked begrudgingly impressed.
"Well, look who finally got a little interesting."
"Don't worry, I'm sure it's a fluke."
Soon after, Dan excused himself when Blair started talking outfits, perfume and lingerie with Serena. Now he played the waiting game, and sure enough, a few hours later, Blair called him.
"Hello?"
"I just wanted to thank you for encouraging me to throw myself at Chuck." She instantly began to scold him. "I can skip dinner now that I'm so full on humiliation. Chuck was completely unmoved."
"Well, are you sure he wasn't just acting like it didn't work?"
"Unfortunately there was no hard evidence of that. Literally." Dan winced, he didn't want the details. "I didn't even get the chance to show him my necklace tangled up in my hair. That nape of the neck is Chuck's kryptonite."
"Oh, that's good to know. So, he just got up abruptly and left?"
"Like a Bass out of hell."
"Well, then, you got him right where you want him, trust me. Right now he's heading home, intercept him." Dan heard Blair pause, another moment where he expected she didn't want to acknowledge that she thought he was right about something.
"I'll let you know what happens." She hung up quickly.
"Oh, please don't." Dan said to himself, knowing that actually he would need to know at least a summary of what happens.
Luckily, he and Serena got a play by play as Blair couldn't stop texting her when she and Dan were trying to hang out. Blair had started out cocky, but Chuck caught her out and she was rejected again. Dan had to admit that he was surprised, he had known for a while that Chuck and Blair had a strange pull on each other, no matter how much it disturbed him, and he had been sure that Chuck wouldn't be able to resist Blair. From what Blair had told him, and what he knew about being a man, Dan knew that Chuck wanted Blair, so his reasons for keeping her at arm's length confused Dan. Did he really want Blair to tell him that she loved him that much? Or was it just to have power over her?
"Please, talk to her." Serena urged, dragging Blair into the gallery the next day and then leaving her in Dan's hands.
"You and Chuck have been toying with each other forever, so you didn't win this one, do you ever think that maybe you should just let it go?" He asked her casually, screaming at himself internally for suggesting the opposite of what he's supposed to be trying to do.
"This is different." Blair snapped desperately.
"Why?" He asked, but she couldn't give an immediate answer. He observed the defeated, vulnerable look on her face and it clicked. "Do you love him?"
She didn't have to answer, she just looked up at him weakly and confirmed what he already knew.
"Wow, someone loves Chuck Bass."
"I don't know." She finally spoke, burying her head in hands, the brushing her hair out of her face. "I just…I don't understand how it got to this place."
"You know the first time I told Serena I loved her, it was terrifying." Dan began, looking down at his tensed hands, having regained his self-control and trying to find the words to push Blair to Chuck. "I've never felt so exposed. But, the feeling I got when she said it back to me…it was probably the single greatest moment of my life."
"But, you broke up."
"Yeah. Doesn't meant I wouldn't do it all over again."
"If I say it, he wins and if he wins, then I'll just…be another girl to him." Blair admitted whilst holding onto her composure.
"You don't know that that's true." Dan replied, hoping that he was right. He didn't want to push Blair towards Chuck only for her to get her heart broken. But the alternative, Blair actually being with Chuck, didn't seem much cheerier to Dan. "You have to decide what's most important to you, keeping your pride and getting nothing, or taking a risk and maybe, maybe, having everything."
Blair left still undecided, but Dan knew he had gotten to her and that on some level she knew he was right. Now, it was just a question of whether she was brave enough or not. Dan couldn't help but think about how Shapiro would love this.
"Was that Blair you were talking to?" Rufus interrupted Dan's thoughts when he came and started stacking up chairs so there'd be more room later.
"Uh, yeah. Listen Dad, I know you don't get this whole Blair thing, but-"
"But, what?" Rufus stopped him from rambling, cutting to the chase in a tone that Dan knew meant that Rufus was willing to listen and wasn't going to chastise him again. Or if he was, he'd be doing it in that subtle indirect way that he preferred to.
"It's just…I don't know about…you know Chuck Bass, right?" Rufus nodded. "You see, Blair…Blair wants to be with him and I encouraged her to tell him how she feels, but…I don't know, Chuck is not a good guy. What am I supposed to do? Tell her what I really think? Or…encourage her to do what she wants?"
"Well, if she came to you as a friend, than you should do what a friend would." Rufus said cryptically, crossing his arms and giving Dan that pseudo-criticism that he knew was coming.
"Which is what?" Dan ignored the passive-aggressiveness, and just hoped Rufus would give him a straight-forward black and white answer, as, for once, Dan wasn't so sure what the right thing was.
"When you think someone you care about is going to make a mistake, you have to let them explain that to them. Then when they don't listen to you, which is what most often happens, you support them and hope that you're proved wrong. But, if you're proved right, then you're still there for them." He advised in a subdued but authoritative tone, then left Dan alone with his thoughts. Five minutes later Serena text him to tell him that she and Blair would be coming to the opening that evening and that Blair had invited Chuck too.
He rationalized. His current go-to coping mechanism. He would do what Rufus had suggested. Take Blair aside. Remind her that even though she loves him, Chuck is still Chuck. Then whatever she does afterwards is up to her. And he doesn't have to feel bad about writing down whatever ends up happening, because if it's terrible, then he had tried to warn her, and if it's not, then no harm done.
When Dan saw Serena and Blair arrive, he locked eyes with Rufus who had also seen them arrive. Dan hated seeing the look of disapproval coming from his father, but he just hoped that sooner or later, his father would understand why he was doing what he was doing.
"Hey. This is a huge turnout, Aaron must be thrilled." Was Serena's greeting. Dan paused, he didn't even realize that Serena had met Aaron, then she added; "And your dad."
"Yeah, it's pretty exciting." He responded, not sounding that excited, already thinking how he was going to word what he needed to tell Blair. And how he was going to get her alone before she went to meet Chuck.
"As fascinating as this is," Blair began, "shouldn't someone be handing out drinks?"
"Let me see what I can about that for you." Dan assented and headed to the café area, dodging Vanessa and hoping that Blair would come find him once he didn't bring her a drink. She didn't, but he soon saw her heading down the corridor to the stairs, and banged on the window to get her attention.
"Hey, stay there." He told her through the glass, then quickly went to meet her. "Blair, I need to talk to you."
"I can't. Chuck's waiting for me." She responded, sounding innocently excited. Dan almost hated that he was going to ruin that for her.
"I know, it's about that…I just think you should be careful." He began to explain, wincing at his own words.
"Why? You said to be the opposite of careful. You told me to take a risk."
"Right, I know, I know, but I…it was bad advice. Because I was thinking about how things were for Serena and me. But we're talking about Chuck here. Do you really want to go down this path with him of all people?"
"What do you mean by that?" Blair asked quickly, the corner of her lip curving up slightly like she wanted to smirk.
"It's Chuck." He repeated quietly but forcefully.
"Of course," Blair's condescending smirk appeared fully, "it's Chuck and Dan Humphrey doesn't approve."
"I've tried not to judge you and your love life for Serena's sake, but when it comes to attempted rapists…yeah I judge." Dan snapped. He hadn't planned on saying that out loud. "And maybe the fact that he assaulted Jenny isn't a big deal to you, but let's not forget he tried to rape Serena too, so you'd think that-"
"What are you talking about?" Blair quickly cut him off and Dan saw the genuine shock on her face, not just because of his outburst, but the content of it.
"Serena never told you?" He asked back, but Blair's demeanour changed and the mask was back on.
"He's changed now. You'll see." She stated and then rushed away before Dan could say anything else. He stayed in place wondering if he said the right thing, and found himself once again questioning who Blair really was if she could so easily excuse a guy who had tried to force himself on her best friend. But maybe she hadn't. Maybe she just didn't believe him. He went back to the gallery and tried not to think about it and enjoy his dad's big night.
"Hey, do you know what happened?" Serena cornered him in a panic minutes later. "Why's Blair so upset?"
"Uh, look, Blair and Chuck…it's not a good idea, so I just…kind of helped to-"
"You intentionally sabotaged Blair?" Serena cut him off before he could explain more.
"No, I didn't intend to…well, maybe."
"I don't understand, I thought you wanted to help Blair! I thought you'd help her be brave." Serena stormed off. Dan still wasn't sure if he had done anything wrong, but he couldn't resist running after her out onto the street.
"Serena, wait! I'm sorry!" He called as he caught up to her, and to his surprise she didn't walk away from him. "What happened, it wasn't….you didn't let me explain. I was trying to help Blair."
"How?" Serena snapped, stopping to glare at him. Her arms crossed and an expression saying that she didn't expect any answer could satisfy her.
"Do you really think Blair should be with Chuck?" Dan raised his voice at her for the first time, not understanding how she of all people would trust that guy with anyone, let alone her best friend. "You told me what he did to you last year, that he tried to force himself on you….and do I need to remind you of our first date which ended with us having to go rescue Jenny from him too? How can you think it's a good idea for Blair to get involved with a guy like that?"
Serena's arms dropped, and she looked to the side, left a bit breathless by the question.
"Chuck's not my type…" Serena slowly tried to explain, "but if Blair loves him, then…"
"Then what?" Dan asked, but Serena didn't have an answer. "Serena, I'm sorry, but…I talked to Blair and I brought up what Chuck did to you. I didn't realize you never told her, but I just thought you should know that now she knows. Why didn't you tell her about it?"
"I don't know." Serena sighed. "Blair and I weren't friends at the time…I just wanted to forget it. Nothing really happened, so it wasn't a big deal."
"Yeah, nothing happened because you fought him off. What if you hadn't been able to?"
"He's my step-brother Dan, what would you have me do?" She crossed her arms again.
"I realize that, and I know that you and Blair and Nate and Chuck have this…weird friendship where you don't seem to hold anything against each other. And hey, as much as it pains me to say it, maybe Chuck isn't a completely….evil guy." Dan winced, it did literally pain him to try and see any of the redeeming qualities in Chuck that Blair and Serena seemed to see. "But I could never trust him. Could you?"
"Look, Dan, I get why you did what you did and I'm sorry that I yelled at you. I just saw Blair so upset and…I'm sorry."
"It's okay, I'm sorry too. For all of it….except for what I said to Blair. I think I did the right thing."
"Maybe. Still, that won't Blair feel any better." Serena shrugged dejectedly and took a deep breath. "I should tell you that Aaron asked me out. But I said no, because I wasn't sure how you would feel, but I kind of want to say yes."
"Okay." Dan took a deep breath. "I like Aaron, he seems like a good guy, so if you want to go out with him….you should. I'm fine with it really."
Dan was surprised how true what he was saying felt, and Serena seemed to register his sincerity too. She asked him if he minded if she went to find Aaron, which he didn't, he had someone he needed to see himself.
Dorota trusted him. That was strange to Dan because…everyone else in Blair's world would never let a random Brooklynite into her penthouse this late at night, but he explained that he knew Blair was upset and that he had something to do with it and he wanted to apologize to her. Dorota told him that Blair was up in her room, then busied herself and left Dan to find his own way up the girl in question.
He felt uncomfortable taking that first step on the stairway. He had intially thought that Dorota would go and tell Blair that he was there, and then probably return alone to send him away, or that Dorota would formally deliver Dan to Blair's room. He felt like he was intruding upon something heading up there on his own, he saw her bedroom door open however and was relieved that at least he wouldn't be walking in on her while she was getting undressed or something like that. That thought lingered in his mind slightly longer than it should.
As he stepped towards the door, he hesitated when he caught sight of her sitting in front of her vanity desk. Her room was darkly lit but, as she removed her earrings, Dan could see in her reflection that she had been crying. He immediately felt even worse. But this also stirred in him even more of a determination to apologize to her and make any attempt to alleviate some of the pain that he was partly responsible for. Still, he loitered in the doorway because this was such a rare sight. Blair Waldorf, completely herself. No act, no mask, no endless stream of putdowns that Dan had started to realize was just her defence mechanism. Just Blair Waldorf. Without all the expectations that came with that name. Just a beautiful but broken-hearted girl.
He gathered the courage and pushed the door open slightly. This didn't take her by surprise, but when she saw it was him in her bedroom shock manifested itself in her widened eyes and slightly gaping mouth. She recovered quickly, swallowed away her surprise and turned back to the mirror, brushing her hair with her fingers.
"Haven't you done enough damage today?" She asked, all business now.
"I didn't mean to do any." Dan replied, as he took a step further into her room and wondered if maybe he had intended to cause damage. To who and why he couldn't consider. "I came to apologize. I know that things went awfully with Chuck and…I cannot apologize for what I said to you, but I'm sorry about the way I said it and my timing."
Blair looked back at him and he now stood a foot away from her. His hands were shoved apologetically into his pockets and the expression on his face was completely sincere. As much as she wanted to, she was too exhausted to think of any verbal abuse she could throw at him to make him leave.
"Serena never told me." She confirmed, devastated. "If I had known…are you sure?"
Dan paused. Blair looked at him with so much desperation, she wanted him to say it wasn't true. That he had been angry in the moment and lied, or that there had been a miscommunication with Serena. She wanted to believe that Chuck was her prince, but Dan couldn't give her that lie.
"Yes. I uh…I told Serena that I told you, so I guess you two can have a long heart-to-heart about it tomorrow."
"I can't believe she was going to let me tell him that I love him." Blair looked down at her hands.
"Her heart was in the right place." Dan said, trying to help smooth over at least some of the damaged he had caused that night.
"As, I now see, was yours." Blair looked back up at him.
"I'm sure that, coming from me, this means absolutely nothing to you, but…you deserve better, Blair."
"Better doesn't…." Blair stopped herself from expressing whatever her immediate reaction had been and recomposed herself. "Better doesn't want me."
"Hey, that's, that's not true." Dan urged, but Blair looked away, not wanting to hear whatever cliché he was going to come up with next. "Hey, you listen to me, listen." He urged her, kneeling at her side and looking up into her heart-breaking eyes and he took a deep breath before he started again. "I can't pretend that you're the perfect woman, that you're completely flawless and any guy who doesn't agree with me is crazy. You have your flaws, I'm very aware of them, seeing as I've been the guy on the other end of your elitism, manipulation, bullying and all round-abrasiveness since I've known you. And yet I can't deny that you're…kind of special. Most of the world only gets to see all the flaws, and despite your efforts to stop anyone from seeing what's underneath, I have. And I'm….stunned. You're…you're annoyingly intelligent and witty. Unfortunately, you often use these powers for evil. You are so determined and so hard-working. You don't let many people in, but those you do….you give so much. Like with Serena, the way you two are….okay, occasionally you're awful to each other, but it's so obvious that you would go to the ends of the Earth and back for her. Not to mention, that you are…. extraordinarily beautiful. You're good traits far outweigh your bad ones. But unfortunately, you seem to have this tragic flaw. You are so terrified of being vulnerable that you hide away who you really are because you so sure that it won't be good enough for anyone else. You…you don't think you deserve good things in your life. It's like you have this really low opinion of yourself….and that's a shame because if you could only see what I see."
Dan shook his head lightly as he finished, and up until that moment it was as if he was in a bubble. A bubble where…everything he'd been trying to cling to was gone. He still wanted to see Blair the way he used to, but he simply didn't anymore. He had been so busy looking at Serena for all those years, that he never truly saw the girl standing next to her. Now, he couldn't possibly tear himself away from her. In the bubble it was okay to feel that way. But when he looked up into her tear-filled eyes, reality came crashing back and he knew that he had crossed a line. He wasn't exactly sure what line he had crossed, but he had and it was irreversible now. Blair smiled down at him as a tear fell from eyelid, staining her cheek. He reached up and wiped it away, unable to control himself. As he lightly pressed his thumb into her flesh, she closed her eyes and seemed to lean into his hand as he pulled it away. They locked eyes again. Both unsure what to do next or what could possibly be said now.
"I should go." Dan broke the silence, although in his head there was an abundance of thoughts rushing around, it seemed like anything but silent to him. He stood up and Blair kept her eyes on him as he politely smiled at her and turn to leave.
"Dan," she called quietly when he reached the door and he turned, "thank you."
Dan was stunned again. Not only had she called him Dan, but she had thanked him. That moment he realized that something was changing, the Claire Carlysle story came into the forefront of his mind, and guilt took over. He smiled at her and gave a slight nod, then turned and left.
When he got home, he couldn't write.