"Let me be blunt, Humphrey. These stories are no good."

"What? I….you said my last one was…." Dan trailed off, wishing that he had gotten into the habit of knowing what he was going to say before he started to speak.

"It wasn't bad. These are just…more of the same." Noah Shapiro casually threw the story onto his desk, either completely blind or simply indifferent to Dan's discomfort.

"Ok." Dan nodded solemnly after taking a deep breath and preparing himself for further criticism.

"You sent me five stories. All about a sheltered young man with girl trouble, who lives with his daddy in Brooklyn. You think that's going to knock the Yale English department off their tenured asses?" Shapiro's asked, his voice getting louder towards the end of the question.

"I…I just, I thought that a writer is supposed to write what he knows. This is what I know."

"Then learn something new. Get out of your comfort zone."

"I wouldn't know where to begin." Dan sighed, just about ready to accept failure and find a new way to distract himself from the recent Serena breakup.

"What about this Claire Carlyle character?" Noah asked as he picked up Dan's story again and casually flipping through the pages. "Now she's interesting, complex, why don't you write from her point of view?"

"What? She's the villain. She's the one who tries to make my life-" Dan stopped himself, shook it off and then continued, "Dylan's life a living hell."

"You're judging the character, Humphrey! You think Capote got national acclaim from In Cold Blood by judging the murderer?"

"I'm guessing no." Dan relented, knowing that no matter what he said now, Noah would only be pleased once Dan agreed to make Claire Carlyle the protagonist in his next story.

"Dig beneath the surface, find the character's humanity."

"That might be difficult."

"We all have a secret. A writer's best tool is the ability to draw out a subject's secret and use it. Bring me back a story with teeth." Noah finished, tossing the story on the table once again and dismissing Dan.

Dan picked up the papers, glancing at the red writing scribbled all over it, and left asking himself how the hell was he going to write a story about Blair Waldorf?

Dan read through the notes over and over. He was relieved to find that none of the criticisms really were to do with his writing style per se, just his plot and characters. Unsurprisingly, that didn't bring him much comfort. He heard Noah's voice in his head as he read the notes, Sabrina has no depth, Dylan is too naïve, their completely idealised love story sounds like the wet dream of a forlorn fourteen year old boy. Which it once was. Dan thought back on his time with Serena and still couldn't believe that it all had actually happened. He had got his dream girl.

In his mind, Dan replayed what he thought was all their time together, though really it was just the happy times when she was all smiles and hormones, before he remembered how she had made him a pariah at school and all the not so happy memories came back. He then also remembered that he was supposed to be moving on and focusing on his future, that's what this whole possible mentorship with Noah Shapiro was meant to be about. Maybe it wouldn't be such a bad thing if he wrote a story about Blair instead, at least he knew that he wouldn't idealize her character.

Still, sat in front of his laptop with an empty word document in front of him thinking about Blair Waldorf was not inspiring to him. He decided to look over his old stories, which really were just diary entries, trying to search for Blair's humanity somewhere in there. He went over a year back, finding mentions of a girly package of evil or Constance's Hitler in high heels here and there and eventually came across the day of the photo shoot that never happened.

As he read the words he pictured Blair sitting against that wall again, how young and vulnerable she looked. For once, her innocent appearance didn't make him internally shudder because he knew she was really a wolf in designer clothing. She had seemed….genuine. Dan had forgotten about Blair's mommy issues, probably because in that conversation she never really gave anything away, all he knew was what Serena had told him; Blair's mom chose Serena over her.

He quickly typed that sentence in the blank document, hoping it would trigger something else. Which it did.

"You take everything from me! Nate, my mom, you can't even help it, it's who you are."

Nate. Serena and Nate. Dan had pushed that from his mind too, but he tried to separate his emotions from the situation and focused on the facts. Blair's long-term boyfriend cheated on her with her best friend. So she had been hurt, sure, but that still didn't make her human. It didn't justify the way she acted and maybe if she was a nicer person, her mom wouldn't choose Serena over her and Nate wouldn't have cheated on her with her best friend. Dan had to reel his mind back in, he had gotten emotionally involved again. Clearly finding Blair Waldorf's humanity would be a trickier task than he thought.

He spent the next hour or so continuing to look through his old entries, finding titbits here and there. He came across a few lines about how he didn't trust Blair with Jenny, that she ended her seventeenth birthday party crying over Nate, that something went down on thanksgiving that somehow resulted in Serena bringing her to the loft and….she wasn't totally unpleasant. When he came across the pregnancy scare a wave of anxiety came over Dan as he remembered the panic that consumed him when he thought it was Serena, then how Blair had nearly left town after the truth about her and Chuck came out, how she fought for her queen B status back, how she had fiercely protected Serena during the Georgina Sparks incident – Dan hadn't seen it back then, but was starting to see it now – and how they schemed to get rid of her together. Then there was a summer's worth of nothing, a mention of her throwing a party for the Lord she had dated and it all ended there.

Dan copied and pasted every mention he had of her into the document he had entitled 'The Waldorf Riddle', and then set about rewording every sentence so that it was described by an omnipresent narrator instead of from his own point of view. He wasn't ready to write from her point of view yet and couldn't imagine how he could possibly get there. Once he was finished Dan had to admit that Blair did lead an interesting life, it was full of scandal, gossip and a high school hierarchy. If you weren't forced to live in it like Dan was, it probably was compelling.

Just when he was starting to wonder where to go from there, the sound of the door slamming and rushed footsteps entering the loft distracted him. He peaked out from his room to see Jenny rushing around, her hands full of folders and a cookie in her mouth.

"Jen, what are you doing?"

"Just grabbing some food before I've got to get to Eleanor's fashion show." Jenny explained as she awkwardly held the cookie in her hand and tried to catch its crumbs at the same time as she was balancing the folders in her arms.

"Oh. There's a Waldorf Designs fashion show tonight?" Dan tried to ask casually as he crossed his arms. "Will Blair be there?"

"If that's your roundabout way of asking if Serena is going to be there, then yes Blair will be there backstage, and Serena will be in the front row with all her socialite friends."

"Can I come?" Dan asked, feeling like he was in a daydream and he couldn't have possibly really asked that question. But he knew that old diary entries could only give him so much, he needed to see Blair and try and observe her with a neutral eye. "It's not about Serena, it's…I just want to see what you do, I'm really proud at how well you've been doing at Waldorf Designs."

Jenny raised an eyebrow as she munched on the cookie. She clearly didn't believe him, but didn't have time to push the matter any further.

"If you get in anyone's way you are not my brother and I didn't get you in ok?" Jenny asked, picking up the folders that she had put on one of the stools.

"I won't get in anyone's way." Dan put his hands up defensively and then took some of the folders from her arms.

"Come on then." Jenny huffed, her head too busy going over the fashion show to either deny Dan or analyse his real motives.

Dan was definitely out of his comfort zone. He tried to convince himself that that in itself was an achievement, but with it came the constant feeling that he was one clumsy move away from humiliating himself and somehow ruining the fashion show. He stuck to the corner, he tried to linger near Jenny but that girl rushed around too much and he didn't want to risk a collision. He told himself to just observe, that's what a good writers does, observes human behaviour and uses it. He needed to sharpen that tool, he thought to himself as he absentmindedly leaned back onto a rack of dresses and paid no attention to the bean-pole models traipsing past him.

"What do you mean the models are gone?"

The panicked tone made him jump and he saw that awful Eleanor Waldorf wannabe hounding a stressed out Jenny and gleeful looking Blair in the background. Considering he'd come to observe, he'd done pretty much nothing but come up with metaphors for the skill of observing.

He caught up to speed and as much as he wanted to know how Jenny was doing, he fought to keep his focus on Blair. There had been a mix-up with the models, but luckily Serena and her friends were happy to step in. This however did not make Blair happy, considering this was saving her mother's fashion show and possibly her career and reputation, Blair seemed pissed off. He couldn't get her. He lounged in one of the abandoned hair and make-up chairs as he saw her suddenly begin to walk with purpose when she came across a green dress, she picked it up and rushed to the changing area with a smile on her face.

Dan knew that he obviously couldn't follow her into the changing area, but soon saw Serena walking the runway in the dress that Blair had been holding. For a moment it seemed like she had done something nice. Then Jenny approached Blair, a similar green dress in hand, she was shortly followed by Eleanor at which point Dan gathered what Blair had done.

He was pissed. She was endangering Jenny's job and Dan knew it meant the world to her. And for what? Just because she could? Dan wanted to step in, wanted to give Jenny a supportive hug and rat Blair out to her mom. Luckily, Dan was not a man of action and spent far too long a time thinking about what to do and the opportunity to do it slipped away. Eleanor was gone and Jenny seemed to be confronting Blair herself. Dan stepped closer, desperate to hear what was being said, only the smallest bit because he was trying to get insight on Blair, mostly because he wanted to see that Jenny was ok.

"I waved the white flag at school, why can't you just claim your throne and leave me alone?"

"Because I can't!" Blair snapped, and Dan saw that there were tears in her eyes. Then both he and Jenny followed her gaze to Serena, who was still bathing in the spotlight.

"This is about Serena. I didn't realize." Jenny said, speaking what Dan was thinking.

"And why would you?" Blair mumbled, her eyes focused on the floor.

"You might be privileged, Blair, but you work for every single thing you've achieved. Like me." Jenny said, no longer speaking what Dan was thinking, but Dan was hooked everything she said. "Serena just glides through."

"Tell me about it."

"I wanted to be your friend last year for a reason. I wanted you to like me." With that statement, Jenny shrugged slightly and walked away, but Dan stayed rooted in place as he saw Blair gaze back out to the runway, her eyes on Serena, just like everyone else. Except Dan, whose eyes stayed on Blair.

Dan kept his attention on her as Blair gathered herself and joined her mother, Jenny and that godforsaken Laurel woman. He watched in astonishment as Blair stuck up for Jenny and convinced her mother to take her final bow, at this point Dan finally felt safe to approach Jenny and put an arm around her.

"You did great, Jen." He told her with a smile.

"Thank you." She replied quietly.

Everyone relaxed, they still had work to do, but the pressure was off now. Dan helped Jenny hang up some of the dresses that the emergency models had discarded on the changing room floor and shortly after everyone was given champagne to toast the success. But surprisingly that's not all they toasted, Jenny got the recognition she deserved too and Dan was beaming with pride.

As everyone stood around with their champagne while they did the few last jobs they needed to do before they could go, Dan saw Blair sneak off. For a moment he thought he'd seen enough of her for tonight, he'd got plenty of material, but she had repeatedly shocked him throughout the evening, first with her callousness, then her sensitivity and then her kindness. He knew he couldn't let the opportunity slip away. By the time he found her she was already talking to Serena, he lingered behind a curtain and eavesdropped on the two.

"You know about the dress." Blair's voice said guiltily.

"Yeah, Laurel told me. She said it was an accident, clearly she doesn't know you."

"I'm sorry. I was hurt, ok? You blew off our most beloved tradition." This didn't seem like much of a reason to get upset, but Dan could hear the how injured Blair was.

"Just get over it, Blair." Dan was shocked, did Serena really just say that? He must have misheard.

"Excuse me?"

"My whole life I have been bending over backwards to protect your feelings. And you know what? It's not my fault you're so insecure."

"And I'm sure it's not your fault you're so conceited."

"I'm just tired of trying to hold myself back so I don't outshine you."

"Oh my God, can you hear the words that are coming out of your mouth?"

"Just the truth." Serena stated coldly. "From now on, I'm going to be who I am and if you can support that and not be threatened and competitive, then great. If not…."

Dan stood, frozen in place as he listened to departing footsteps. He'd seen, or heard, the less than perfect side of Serena before, and recently he'd been on the receiving end of the queen S phase she seemed to be going through at the moment, but he couldn't get over that Serena had just said that. He ignored the second steps of footsteps leaving, forgetting momentarily all about Blair, thinking only about Serena and the illusion that had just shattered in front of him.

He told himself that he probably had missed a lot, that Blair must have provoked her, which he was completely sure was true but what had happened still didn't sit right with him. Serena just sounded so….arrogant. A trait that he disliked in anyone. It didn't make sense, he had known her for a year, he had never seen her act condescendingly to anyone, let alone her supposed best friend. He told himself that he was probably reacting so strongly because he had seen what Serena hadn't that night, he had seen Blair standing in the shadows, desperate to be the one in the spotlight.

He remembered Blair and that she was the one he supposed to be scrutinizing. He stepped outside and watched Blair watch Serena, who still had everyone's attention and a group of photographers desperate to get pictures of her. Then she was gone, flashes of light still exploding as her car drove away. Blair lowered her head as she turned back towards the building and started to ascend the steps. She stopped on the bottom step when she saw Dan at the top, staring down at her. They both froze, a subdued look of realization appeared on her face as she read Dan's shocked, yet sympathetic expression.

The moment was lost however when he heard his dad's voice and turned to see him dragging Jenny out, appearing to be in the middle of a tirade. He glanced one last time at Blair, who gave him not only a look that said he was free to go, but that she wanted him to get away from her now. He obliged and ran after his dad and Jenny, only now catching up on the fact that Jenny wasn't supposed to be at the fashion show and that he was now in trouble too for apparently aiding and abetting her.

Once Rufus had cooled off and Jenny had gone to bed, Dan holed himself in his room, desperate to type up everything that had happened, not wanting to forget one detail. He wrote everything that he'd seen from Blair and what he could figure out from that. Clearly her issues with Serena ran deeper then he knew, and once again Eleanor had chosen Serena to wear her designs instead of Blair. Clearly the mommy issues affected Blair more than he had thought, the sabotaging Jenny, it wasn't about Jenny at all, she was just begging for some attention. Maybe that's why she did a lot of things that she did. Her dad wasn't around either, the closest thing Blair had to a parent was Dorota. The closest thing she had to real family was Serena, who she seemed to simultaneously adore and loathe. Dan could finally understand why.

That night Dan sat up writing everything he knew about Blair, trying to figure out an answer to a question that no one had asked before. He typed until his fingers began to cramp and staring at the screen started to hurt his eyes, only stopping when he saw the sunlight beginning to creep in. He decided to get a few hours of sleep before he had a chance, but his mind refused to shut down, too consumed by the shock that maybe Blair was human after all and the unsettling feelings the maybe Serena was only human after all.