This chapter is a bit different as Dan interacts with a few different people, one specifically he hasn't spent time with yet in this fic, but it was a storyline from the show that I really wanted to incorporate into this fic over the next few chapters!
"Humphrey, readers want romance." Shapiro said forcefully as he leant forward over the table like he was about to jump over it and strangle Dan.
"But, that's not true at all." Dan argued, he knew he was right so he wasn't scared to argue this point. Shapiro himself had never been one for romance, so Dan didn't know how he of all people could be saying.
"Yes, clichéd romance won't interest the cultured and intellectuals and literary geniuses. What I mean is, the readers that will be reading your story, will want a little romance in there to stir things up."
"What readers…..what?" Dan asked quietly, feeling quite lost.
"I passed the last few chapters on Blair Waldorf along to a friend of mine. He liked them. If you can polish them up a bit more he'll publish them in New York Magazine." Shapiro responded with a knowing smile, casually giving Dan the biggest news of his life.
"New York Ma…." Dan was in disbelief, he didn't know what to say. Then reality hit in. "No, I can't publish this. If Blair, or Serena find out about this, I'll-
"Humphrey, who, out of the people who are going to read this, will be able to figure out that this story is about Blair? Besides, we won't use your real name. Nobody will know."
"I don't know…I'm not exactly what you call lucky. Generally, in my life, what can go wrong will go wrong. In fact, I've been tempting fate just by writing the story." Dan rambled, waving his hands around as he spoke, but Shapiro's seemed completely settled during Dan's outburst.
"Do you want to be a writer?" He asked as he pulled his glasses off.
"Yes." Dan replied after an initial hesitance, but when he said it they both knew he meant it.
"Then you're just going to have to decide how much you want to be a writer." Shapiro stated, then he relaxed back into his chair. "I'll give you some time to think about it. In the meantime, James Wolfe, the director at New York Magazine, wants a slightly different angle on the story. He was thinking that it can be an expose on the Upper East Side teenager of sorts, emphasis on the parent's involvement, or lack thereof."
"So, you're thinking…basically he wants it to be about how all the people seem to have it all on the outside, but on the inside they're terrible people who torment their children, thereby turning them into terrible people and it's a vicious cycle?"
"Something like that." Shapiro agreed. "We want more about Claire Carlyle's childhood, find out what made her the way she is."
Dan brought his hand to his brow and took a deep breath as he thought about whether he could agree to this or not.
"I'll see what I can come up with. And about New York Magazine-"
"You can think about it. But if you decide that you don't want to have your work published, don't bother with the next chapter, don't bother writing anything if you don't have what it takes."
Dan's jaw tensed. With that ultimatum hanging over his head, Dan pushed his chair back from the desk and marched out of Shapiro's office.
Dan spent his journey home thinking about how much he hated Noah Shapiro. When he first got the internship with him, Dan felt elated and had tried not to let himself get carried away imagining the comradery that would grow between them, the collaborations they might work on and how Shapiro could change his life. Then, when Dan actually starting spending time with Shapiro, he had tried to paint him as an eccentric to excuse his brashness and callous candour. That only lasted a few days until Dan was forced to admit to himself that he hated Shapiro. Real hate, not just dislike. But he had never stopped respecting him.
That's why Dan had utilized this opportunity as much as he could. Shapiro wasn't going to coddle and protect him. He was going to be cold, condescending and crass, but it would make Dan a better writer. That's why Dan had told himself that he was going to stick it out with Shapiro no matter what it took, because he knew that in the end, he would be better for it.
For the first time, he was starting to doubt that belief. He wanted to go to someone for advice, and usually the first person he would turn to would be his dad, but Rufus had already made his feelings on Dan writing about Blair perfectly clear, so Dan knew that he couldn't be objective about this dilemma.
When he got home, Jenny was holed up her room with that model friend again and made it clear to Dan that she didn't want to be disturbed. Which he was fine with, because he didn't want to be disturbed either. He had a childhood that he knew nothing about to analyse.
He knew that Blair's mom had always been critical and dismissive towards her, and that she'd been a daddy's girl up until he left, but Dan just needed a few details. He thought about Serena first. He could somehow coax an anecdote or two out of her, but he'd had to carefully monitor himself about how much he talked to Serena about Blair. But despite Serena's endearing cluelessness, he couldn't think of a way to get her to divulge information about Blair's childhood without making her suspicious. The next person he thought of was Nate. Since Yale, they'd hung out a few times as Nate still seemed to be on the outs with Chuck for whatever reason. It had seemed at first that Nate had really been trying to hang out with Serena, but she'd been quite busy with Aaron, so Dan and Nate, her two former flames, were forced together.
Not that Dan minded, Nate was a good guy and not to mention a laidback guy, being around him made Dan feel calmer. Craving a careless afternoon, Dan called Nate and made plans with him, forgetting that his main objective was meant to be digging up information on Blair.
He headed to Nate's place, but when he got to the gate, he found a seized notice on the step. He headed around the back way and called for Nate as he searched through the rooms. There was no furniture and when he flipped the light switch they didn't come on. At that moment, Nate began to call him.
"Hey, man." Dan said casually, feigning innocence never having been his strong suit. "Yeah we're meeting at the park. I'll see you in ten."
He hung up and looked over at makeshift bed on the floor, along with a book, some candles and some clothes. So much for hanging out with Nate to help him relax.
"Hey, Serena." Dan had called her the first chance he got, while Nate bought some water. "Have you talked to Nate lately?"
"No, is everything okay?" She responded, having picked up on Dan's panicked tone.
"I don't know, I…I don't know if I should tell you." Dan struggled.
"No, tell me. If something's wrong with Nate, you have to tell me." Serena said.
"Serena! Hang up on that hopeless Humphrey now, I need you." A shrill voice called out in the background.
"Is that Blair?" Dan asked.
"Yeah, she's…got this babysitting problem, it's a long story. What's going on with Nate?"
"I can't tell you on the phone, he's heading over now. Are you at home?"
"Yeah."
"Then I'll bring him over, I'll find a way to tell you about it when we have a minute alone. And hey, if you help me with my problem, maybe I'll be able to help you and Blair out." Dan lifted his arm and gestured as if Serena could see him as she agreed, then he hung up just as Nate reached him, offering a bottle of water.
"Hey, who was that?" Nate asked.
"Serena. There's some kind of…babysitting problem with Blair. I told her we'd go over now to try and help out, if you don't mind." Dan said, shrugging his shoulders and gesticulating dramatically, like he always did when he was trying to act normal.
"Sure." Nate nodded, oblivious to Dan's odd behaviour.
On the way to Serena's, Dan nonchalantly asked Nate if he was friends with Blair now or if it was awkward between them, carefully starting the process that he hoped would lead to Nate talking about growing up with Blair. But Nate seemed down, he generally answered Dan's questions with one word, and when Dan was real lucky, a shrug too. No sooner had they stepped into Serena's living room, did a young, Blair-minion-wannabe strut up to them wearing what Dan was sure was one of Serena's dresses.
"Uh…who are you?" Dan asked awkwardly as the girl seemed to eye-fuck Nate.
"Dan! You're here!" Serena emerged with Blair down the hallway, a big fake smile plastered on her. "This is Emma, we're taking her to the charity gala honoring my parents tonight. Dan, come, I need a guy's opinion on an outfit."
Serena pushed Blair towards Nate and Emma, then grabbed Dan's hand and dragged him to the bedroom, slamming the door behind them.
"Ok, what's going on?" Her tone changed instantly and she crossed her arms.
"I'm not sure exactly. I thought I was meeting him at his house earlier, but when I got there…it was empty. Well, all accept a sleeping bag and some hair products, but…there was a seized notice by the front door."
"Oh, my God." Serena gasped. "Nate, is he-"
"He doesn't know that I went there, so you can't tell him. I just…I didn't know what to do, I hoped that you might."
"I wish I did." Serena replied under her breath. "I'll figure something out, just don't let on that you know."
"Oh, sure." Dan replied and Serena raised an eyebrow at him. "I know I'm not the best actor, but…I only have to fool Nate."
"That's true." Serena chuckled.
"So, what's the babysitting problem? Emma seems like she'd be easy to take care of…"
"Easy? Yes, that's kind of the problem. Emma is Dean Barube's niece, so Blair thought that the two of them could share a wonderful, classy, chick-flick kind of evening together so that Emma would tell Dean Barube all about how wonderful Blair Waldorf is and what a great asset she would be to Yale. But it turns out Emma wasn't thinking chick-flick for tonight, she was thinking….porn."
"Huh?" Dan really hadn't caught any of what Serena had just said.
"She wants to lose her virginity tonight." Serena made it clear.
"Oh." Dan caught up. "So, the charity gala…?"
"Just trying to keep her occupied. You and Nate should come too."
"I would, but…." Dan paused, trying to gather all his conflicting objectives. If he went, it would be a night to observe Blair. Not to mention he'd be with Serena and Nate too and might be able to find a way to ask them some questions about Blair's childhood. Maybe it would help Nate somehow too. If not, then at least Dan brought a few more hours to figure out what to do on that front too. Plus, he had Serena trying to help now too, while he was simultaneously trying to help her and Blair with the Virgin Scary, surely they'd all be better off sticking together for the night. "Why not?"
Dan found Serena at the gala later, when he was scanning the crowd for leggy blondes, he almost thought he saw Jenny, but when he looked back she was gone, so he headed straight to Serena.
"Hey, have you figured out a way to help Nate yet?" He asked straight away, bypassing greetings.
"No." Serena sounded frustrated. "I've spent the last hour casually reminding him of how long we've been friends and that he can come to me with anything with the hopes that he'll confide in me but…nothing."
"And Blair?"
"The human contraceptive? She's stalking Emma." Serena popped an olive into her mouth, just as Blair stormed over to them, like she was just doing it to prove Serena wrong.
"Humphrey, what are you doing here?" Blair focused in on him.
"I invited him." Serena answered for him. "Blair, shouldn't you be watching Emma?"
"Please, have you seen the guys here? No, why? Because there are no guys here, just geriatric menfolk who wouldn't have the competence to pop her cherry even if she wanted them to. Not without medication anyway."
"Ew." Serena scrunched her face.
"Where is she now then?" Dan asked, scanning the crowd, but only seeing the geriatric menfolk that she had described. Blair followed his gaze, looking slightly panicked, but before she could react the lights went down and some music came on.
'J Humphrey Designs' flashed on the televisions screens as a troupe of models marched in and began to dance around whilst giving out pseudo J Humphrey Designs business cards.
"This is why you're here!" Blair turned to him accusingly. "You're helping you're status-seeker sister throw a guerrilla fashion show!"
"What? I have no idea what's going on!" Dan replied clearly taken aback, and Blair, who hadn't really thought he had anything to do with it anyway, knew he was telling the truth.
"I don't have time for this, I have a virgin to find."
"Hey, I'll go with you." Dan said, already falling into step behind her, but she froze in place and turned back to him, giving him the same puzzled look that Serena was.
"Hey Dan, can you believe that Jenny did all this?" Nate asked as she joined the group, then noticed the tension. "What's going on?"
"We've got a virgin to find." Dan took charge. "Serena, grab Emma's photo off of facebook and send it into Gossip Girl so she can put an APB out on her."
"Excuse me, scheming is my thing." Blair whined, pointing to her chest as Serena began to do as Dan has asked.
"Yeah, well, your scheme to bring Emma to this party in the first place didn't exactly work out did it?" Dan responded.
"Oh, and you think all you have to do is send a picture to Gossip Girl and just like that we'll have her location?!" Blair snapped back, and Serena's phone beeped before Dan could reply to her.
"That was quick." Serena said as she checked her phone. "She's at 1Oak."
"I'm lost." Nate stated, hoping some would catch him up.
"We'd explain to you on the way, but you still wouldn't get it." Blair said, grabbing Nate by the arm. "Come on, we've got to go find her now!"
Sitting in the back of a limo with Blair, Serena and Nate, Dan couldn't help but think about how strange this all was. Shapiro had wanted him to do the Shaughnessy thing and write from the inside, but he hadn't imagined it would be so easy to get involved in the weekly schemes and shenanigans of the Upper East Side.
"So, why am I here?" Nate asked, still confused even though Serena and Dan had ignored Blair's previous remarks and had been kind enough to explain Nate what was going on. But it seemed that Blair had been right and Nate still didn't get it.
"Think of Emma's hymen as the delicate physical manifestation of all my hopes and dreams. If it is broken then so are all my chances of getting into Yale and my whole life will be ruined!" Blair snapped.
"Nice imagery, Blair." Serena sighed as she rubbed her eyes.
"We're nearly there." Dan said, trying to calm everyone down and the limo pulled over a second letter.
The odd group headed inside, and tried to wade their way through the mass of bodies that affronted them. Nate headed straight to the bartender while the other three began to explore, Dan went one way while Serena and Blair went another. He did a quick circle then re-joined the girls at the same time that Nate did.
"I found her table." Nate said.
"As usual Archibald, you are behind the plot, she already left." Blair snapped.
"The bartender said she's in the corner booth." Nate added, gesturing in the direction of the booth, the four moved closer to see a middle-aged woman there with some sleazy guy that looked the same as pretty much every other guy in the club.
"That's not Emma, that's her mother." Blair explained.
"And that's not her father." Serena added, as the repulsive couple started to kiss.
"Oh, my God." Blair said, barely containing her glee as she raised her phone to take a snapshot of the pair.
"We still need to find Emma." Dan ordered, regaining everyone's focus.
"Why?" Blair asked as Nate headed back to the bartender for more information.
"Blair, this poor little girl's mother is having an affair, no wonder she's acting out." Serena urged her.
"So, this is my golden ticket." Blair responded, waving her phone with the picture on the view screen in front of Serena.
"You are not black-mailing that woman to get into Yale." Serena grew more forceful.
"Blair, you can do what you want with that picture, but…we can't just go home tonight with Emma God knows where with God knows who doing God knows what." Dan jumped in, trying to bring the two girls to a compromise.
"I got an address." Nate said as he got back to them.
"So, what are we doing now?" Dan turned to Blair.
"Fine, we'll save Little Red Riding Hood from the Big Bad Wolf."
The four headed to the door in unison, as Nate began to chuckle.
"What are you laughing at, Archibald?" Blair snapped.
"I'm just thinking…us four of all people trying to protect a young girl's virtue. Well, maybe Dan being here isn't much of a surprise, but I think it's funny that Blair, Serena and I are doing this."
Forty minutes later, they had grabbed Emma and were escorting her back home. Once they pulled up, Emma jumped out of the car and stormed inside, Blair chasing after her.
"I'm going to go too," Dan explained as he scooted towards the door, "I don't really think that stalking virgins is Blair's niche, not that it's mine, but…four hands are better than too. That still sounds gross, not even going to try with this next one; I'm going to go help Blair with the virgin."
He caught up to the two brunettes in the lobby, Emma seemed pissed, but Blair was surprisingly calm.
"There are better ways of getting your mother's attention." Dan heard Blair say as he edged closer.
"I told you, this is about Muffy-"
"Please. I wrote the book on distracted, self-centred mothers." Blair paused, as Dan stepped by her side. He didn't know why, but he didn't want to eavesdrop on her. He wanted her to know that he was there and that he was listening and, to his amazement, she continued. "My mom has never met a single one of my teachers, she regularly forgets my birthday and she only comments on my appearance when she has something to criticize."
"But you're perfect." Emma responded.
"True." Blair said and Dan smiled to himself. "That's why I finally realized it wasn't about me, the same way it's not about you."
"My mom always says when we come to the city we're going to hang out and do mother-daughter things, it never happens."
"So, tell her that." Blair took a deep breath and looked at Dan nervously before she continued. "When I told my mom how I really felt, it got better."
Dan gave her a knowing smile as her thought back to the time he had been the one to encourage her to tell her mother how she felt, and Blair smiled back. He'd never thought much of the day and whether it had really made a difference to Blair, but clearly it had.
"Come on, let's get you upstairs." Dan broke the silence, leading the two smiling girls to the elevator.
The smiles quickly disappeared though when they went into Emma's apartment and found her mother waiting there.
"Do you know what time it is?!" She snapped. "And look at that dress! You expect me to believe you went to the movies in that?"
"Mom, please don't. This isn't her fault-" Emma tried to explain, but for all her efforts she was sent to bed.
"Mrs Boardman, before you say anything you'll regret-" Blair began, as she stepped towards the woman with confidence.
"What was your plan? You and your boyfriend take my daughter clubbing and hope she'd plead your case to the Dean?"
"He is not my boyfriend!" Blair exclaimed, disgust evident in her voice.
"Mom, I can explain!" Emma rushed back into the room.
"I told you to go to bed."
"Blair was only trying to help me!"
"You're lecturing me? No wonder I don't want to spend time with you, bed! Right now!" This time Emma had no rebellion left in her, and she dejectedly left the room again.
Dan froze in place, looking to Blair who had her phone in her hands, ready to blackmail Mrs Boardman, but she seemed to be hesitating.
"You were saying?" Mrs Boardman turned her attention back to Blair.
"Just…your daughter is a great girl. You should pay more attention to her. Soon it will be too late." Blair said sadly, then she turned to leave and Dan followed her out.
"You did the right thing." Dan broke the silence in the elevator as they rode back down.
"Yeah, well, doing the right thing may have just cost me Yale." Blair replied bitterly.
Dan didn't know what to say. She wasn't wrong. As he shuffled nervously, he put his hands into his pocket and he felt one of the polaroid's for Jenny's fashion line. There was someone who had done something morally questionable for the sake of her future.
"What?" Blair snapped.
"I didn't say anything." Dan replied defensively.
"You were thinking too loud."
"Yeah, I was…I was just thinking about the future. And the lengths that you have to go to sometimes to get what you want."
"Is Dan Humphrey having an ethical crisis?" Blair asked, sounding amused.
"I guess you could say that."
"You'll do the right thing. You always do." Blair said as if it was a bad thing, but then, in a more wistful tone; "Nate's lucky he has you."
"What?"
"Serena told me what happened and that you're trying to help him."
"I don't know if you could call it trying…I want to help, but I don't what to start, I don't know what he needs."
"I do." Blair said with a perky confidence. "He needs a friend. That's why he's lucky he has you."
The elevator dinged as they reached the bottom floor and Blair sauntered ahead as Dan was stuck in place, wondering if Blair had actually just complimented him.
"Humphrey!" She turned back as she reached the door and he snapped out of his trance, and ran to catch up with her as she got back in the limo.
At Blair's demand, she was taken home first, then the limo headed to Brooklyn. It wasn't efficient by any means, but when Dan relayed his address to the limo driver he shared a look with Serena and she smiled at him, knowing what he was doing.
"Come on, Nate." Dan said when the limo stopped.
"What?" Nate was confused, as usual.
"I, uh…I know…about your house. And I know that…the loft isn't up to the Archibald standard, and my dad is probably screaming at Jenny in there right now, so it's not exactly relaxing, but it's…it's a home."
Nate still looked shocked and he looked to Serena.
"Dan told me." She confirmed. "I'm really sorry, Nate. But I think Dan's right, staying here for a while might be good for you."
"At least for tonight?" Dan added hopefully. "I'll take the sofa and you can get some sleep in a real bed."
"I guess." Nate relented, and Dan and Serena smiled instantly in response. Nate couldn't help but smile back at them, but it wasn't quite the same, he was still in shock and a bit embarrassed.
Dan didn't sleep well that night, and not just because he was on the couch, but Noah's words kept running through his mind.
'You're just going to have to decide how much you want to be a writer'
Dan really wanted it. And it seemed like fate, the way that Blair had talked about the issues with her mother on the night when he'd been trying to find out more about their relationship. On some level, he convinced himself that it was a sign, that this is what he was meant to do.
"Did you sleep well last night?" Rufus asked as they began eating breakfast while Nate was still asleep.
"No, I was…thinking about the Blair story." Dan admitted, hoping that he'd be able to share the fact that he would be getting published in New York Magazine with his father, and that he just might be happy for him. "I might be getting an opportunity to get it published."
"Dan, just because Jenny-"
"Dad, the morning after my little sister stages a fashion show that all of New York City will be talking about, is not the time for the slow and steady speech." Dan cut him off, pissed that he was right about Rufus not being happy or proud of him.
"I wish I could get the two of you to understand that success, people praising you, it goes away. And when that day comes, if you don't like who you are…you're done."
"Well, I guess that's a chance I'm willing to take."