This chapter! This is the chapter that I got stuck on for so long. It was the hardest one to write, for quite a few reasons. For one thing, this is where it goes from 'it took me a really long time to get them to a place where they're relatively happy, but all the issues they haven't dealt with are going to come back and tear them apart'. I like angst to a point, but it's going to get harsh and it's going to last for quite a while – but these aren't minor things, these are things that have to be resolved.

Secondly, this isn't from Dan's POV exactly, but the reader only knows and sees what he does and I felt that there's a lot in this chapter that Dan doesn't pick up on. I thought a lot about writing this chapter focusing on Blair instead, but overall, I thought it would disrupt the flow of the entire story. You don't exactly see the best side of her in this chapter, but there are reasons why and I know them, but I just couldn't fit them in here in a realistic way that made sense. Anyway, stick with me here, this is all happening for a reason and it's all building up to the ending I've planned for all along.

Dan felt his heart sink a little as the sunlight began to stream into his bedroom, because he knew that meant she would be gone soon. He held Blair to his chest, his head resting in the nook of her neck, his arm around her waist. He breathed her in. He felt so relaxed, but, the truth was, he never slept easily when Blair was there.

Probably because, he knew that if he fell asleep, she wouldn't be there when he woke up. It was easier at her place. He would sleep. Even though her mom had been away on business a lot, their relationship was still a secret so he needed to get back to his before anyone noticed he was gone. He found that he generally needed to clamber out of her bed at about 4am, because she'd never let him leave straight away. She'd pout as she would grab his hand and drag him back to bed. She'd kiss his neck and pull off the t-shirt he had just put on and whisper to him to stay a little longer. To just lie down with her, to keep her warm. He always gave in.

She'd only stayed at his twice – and even that was a miracle. Blair Waldorf in Brooklyn. In the loft. In Dan Humphrey's bed with his polyester sheets wrapped around her. But she seemed so peaceful. She would sleep, but somehow she'd always wake up just at the right time to either kick him out of her bed, or untangle herself from his. Dan wished they could stay that way forever, in their bubble, where – against all logic – it felt like nothing bad could possibly be happening in the world. That everything was peaceful, and safe, and….right.

"It wasn't what you wrote about me." She suddenly said. It was just above a whisper. "How you wrote me."

Dan stayed quiet. He thought that she was asleep, and thought that perhaps she thought he was asleep too, that maybe he wasn't really supposed to be hearing this.

"It was you." She continued. "Seeing things through your eyes….I finally saw how brave you are. How selfless and caring, even when it hurts. I envy that a little bit. I wish that I could have a heart as fearless as yours."

She sounded dreamy, like she might have been talking in her sleep. She had got quieter as she continued, and Dan had gathered that he wasn't really supposed to hear that. He thought every urge to pull her closer to him, to kiss her on the cheek, as he kept his eyes shut and his breathing even. Even when she unravelled herself from his arms and got dressed, Dan pretended to be asleep – he was worried that if he had to look at her, to speak to her, that he would beg her to stay and he knew that she couldn't. He told himself to just let her go, he'd see her again soon enough.

She was gone, and the room felt cold. The peace was gone and the world went back to how it had been before. It got harder every time. Not just to let her go, but the uncertainty was killing Dan. Why did she have to leave? Why did it have to be a secret? Why couldn't she just tell him what she wanted? They still hadn't talked that much about the terms of their relationship, but Dan was sure that it had to go public soon. They were getting too close – something had to break sooner or later.

Dan still couldn't sleep. With Blair gone and the harsh reality of the real world back upon his shoulders, he had a lot that he needed to deal with.

I hope you're prepared to make it up to me tonight.

Dan smiled to himself as he read the text message. Chapter 10 had come out that morning, and even though every week the story got less and less interesting (and less true), Blair still religiously let him know what she thought of his writing. Even though Dan had made it clear to her that it wasn't even his writing at this point. Although, he did enjoy making it up to her.

I thought I already made it up to you with the short story I gave you the other day

And that's not all I gave you…

As tempted as he was, Dan needed to find a delicate way to tell her that he wouldn't be seeing her that night. They'd been sneaking around for a few weeks, but lately he'd had less time to spend with her and he didn't exactly want her to know why.

Don't get cocky, I've got constructive criticism on both

As much as I appreciate your noble efforts to help me on my quest for self-improvement, I can't come over tonight. Tomorrow?

I'm starting to think that you're taking my kindness for granted

I never take you for granted

Got a family thing tonight, can't miss it

You do realize that Lily and your dad are coming here for Seder right?

What's going on?

"Dan, put your phone away. Time to go to work." The grumpy brunette, Corrine, ordered as they pulled up.

Before Dan could try and come up with another lie to cover the one he had just been caught in, he realized where they had just arrived.

"Oh. Oh, no, no, no." They were outside Blair's building. It just wasn't possible. Fate could not be this cruel.

This was only his fourth job since he started working as a cater waiter. It was pretty much guaranteed that as soon as things started going well with Blair, something else in Dan's life had to go terribly wrong. The morning after his second night with her, Dan found out from his dad that he'd been denied financial aid from Yale – that's what the call about appraising the loft had all been about, Rufus had been trying to figure out how to pay his tuition. It hadn't worked out, but, after coming so close, neither of them were going to give up on Dan's dream quite yet. Rufus had mentioned something that led Dan to believe that Lily had offered to help, but both of the Humphrey men were too proud for that. And so, Dan had to get a part time job (as well as helping out at the gallery) and Jenny and Vanessa were the only ones he was willing to let know about it. Dan figured his dad was too proud, and no one else even knew about the financial problems he faced and Dan didn't want them to. Especially Blair.

It was tricky keeping two secrets at the same time. Between sneaking around with Blair and working a secret job, he'd been having to cover his tracks a fair bit lately, it was only a matter of time before he got caught. As Dan gazed up at Blair's penthouse, he felt the sinking in his stomach as he knew that time had come.

"Good, you're here!" Eleanor had suddenly appeared at his side, Dan couldn't believe that she remembered who he was, let alone that she was welcoming him. "I just ran out to buy some candles, I don't understand why we can't just light some votive. You look familiar. Have you worked for me before?"

That made more sense. She didn't know who he was, she was just happy that the help had finally arrived.

Dan quickly took her aside in the foyer and reminded him that he was actually one of her daughter's friends (well, kind of) and that this must have been a mistake. He had to get out of this somehow. Corinne pointedly grumbled every time she walked past them as she began emptying the van by herself, but Dan was too absorbed to notice. Eleanor saw the delicacy of the situation and Dan was surprised that she actually tried calling Le Petit Oeuf to see if they could send a replacement, but when that failed, Dan could feel the walls closing in.

He considered the fact that nobody could actually physically make him do this. He could just leave. Sure, he'd get fired, but he'd always be able to find another part-time job where he'd get paid minimum wage to be verbally abused by people he hated. But, considering he was hoping to make things official with Blair sooner rather than later, he really didn't want to get on her mother's bad side.

"I'm sure between Corinne and Dorota-"

"Dorota has the weekend off and I absolutely need two servers. Cyrus's mother is coming and she hates me. I have never thrown a Seder before, I don't even know how to say half the words in this prayer book that's named for Lieberman's wife."

"She's Hadasa. I think the prayer book is called Hagada."

"See. You cannot leave." Eleanor paused, taking in Dan's hesitation as Corinne came to stand beside him. "I'll double your pay. For both of you."

"I could really use the money." Corinne said slowly, emphasising each word and raising her eyebrows at him. Dan knew that he needed to money just as much.

"Umm….fine."

So, it was settled. Dan had suffered through a lot of bad days in the last few months, he was sure he could make it through this one. He just needed to keep reminding himself why he was doing it.

He'd not been in the kitchen one minute before Blair stepped in and froze when she saw him. She instantly knew what he was doing there and tried to act unaffected, but Dan could see the disappointment there. She scalded him and Corinne for starting late – betraying no sign that that Dan was any different to Corinne in her eyes – then went into the dining room to straighten out the table cloth. Dan watched her out of the corner of his eye, knowing that she was busying herself till they could get a chance to talk.

It didn't take long to find an excuse as he went to arrange the napkins.

"You're a cater waiter?" Blair wasted no time.

"Yeah." Dan shrugged, his eyes trained on the task in front of him.

"You lied to me?"

"Yeah." Dan repeated, this time genuinely remorseful. "I didn't want you to know. I'm sorry, but I didn't want you to look at me….the way you are looking at me right now."

"Well, what did you expect to happen when you showed up here?" She whispered, but her tone was so harsh that it hurt Dan's ears. Suddenly, they were the kind of couple that had hushed arguments at parties. Not that they were any kind of couple really, and at this rate….

"I didn't plan this, okay? Do you think I want to be here? Do you actually think that being here, serving you and your mom is going to make me feel good?" Dan was starting to lose patience. He didn't get how Blair could actually think that he was actively trying to do something bad to her.

"Then why are you doing this?"

"I need the money."

"For what?"

Dan went quiet again and looked Blair straight in her eyes. He wished he could make her understand, but even if he told her the whole story, he knew that she wouldn't. She stood waiting for an answer.

"Hey, guys." Serena glided into the room with the same ease that she always does.

"Serena, hi." Blair tore her eyes away from Dan with a quiet resolution that let him know that this was not over.

"What's going on?" Serena looked from Blair to Dan, picking up the tension they made little effort to hide. "Dan, why are you….are you a cater waiter?"

"Yes, I am. And I am so glad that you are also here to witness my humiliation. Can I get you a drink?"

Before Serena could reply, they heard Eleanor greeting Rufus and Lily. Dan's heart sank a little more, he'd forgotten that they'd be there. He'd been so focused on Blair and her family, he didn't even think that Serena might be invited and it had completely slipped his mind that his dad would be there. The only thing missing now was Chuck, then Dan could officially declare this the worst day of his life.

"Doesn't your dad know?" Serena asked, reading the panic across Dan's face.

"I guess he's about to." Dan sighed, then walked out into the foyer, with Blair and Serena right behind him.

"Dan, what are you doing here?" Rufus asked with a hesitant smile on his lips.

"Um, I'm just gonna say it- "

"Because I invited him." Serena stated, stepping forward so she stood next to Dan. "Blair invited me and Nate, but he's out of town trying to patch things up with his grandfather, so I thought Dan could take his place."

"That's very thoughtful, Serena." Lily spoke in her usual suspicious and condescending tone. "I'm glad to see that you two are getting along again."

Awkward smiles were exchanged between the four of them. Lily knew when Serena was lying, Dan couldn't ignore her and Rufus's unconvinced expressions, but he knew that they weren't close to figuring out what was really going on there.

"Dan, you're dressed as a cater waiter." Rufus finally broke the silence.

"You go for a classic look with a black tie and a white shirt and that's what you get." Dan said as he rolled up his sleeves. He was very aware of the fact that Blair was still lingering behind him, he could feel her eyes burning the back of his neck.

"Daniel, would you go downstairs and get the kosher wine? And please, make yourself a little more presentable." Eleanor ordered as she trampled through the foyer, not even pausing to greet Rufus and Eleanor.

"That was sort of rude."

"Yeah, you know what? I'm just going to go with it." Dan responded to his father already stepping backwards, completely desperate to get out of the conversation.

Rufus talked art with another of Eleanor's guests and Blair was putting on her very best Mary-Sue impression as she sweet-talked Cyrus's mother, so it was easy for Dan to go unnoticed as he snuck back and forth from the kitchen – even with Eleanor yelling his name every thirty seconds.

It didn't take Dan too long to notice that Serena was helping him out, when Dan was balancing trays on his forearm, Serena would point Rufus and Lily's attention to some décor behind them, or she'd circle round them as she spoke about her summer plans with Nate and they'd unsuspectingly follow her path. Dan was grateful, but at the same time it made him feel even lower. The fact that Blair was obviously wilfully ignoring him didn't help much either. Time had never moved more slowly.

When everyone began filing into the dining room, Dan felt a hand on his arm pulling him back.

"Dan, what's going on?" Serena asked, clearly concerned.

"I'm a cater waiter." He shrugged.

"I noticed. But why?"

"Serena, as shocking as the concept must be for you, not everyone has parents who can buy them everything they ever wanted. Not everyone has the luxury to spend the summer before college travelling the world and having the time of their lives, believe it or not, some people have to work….and work and work and then have to work some more to try and get into college-"

"Wait, this is about Yale?" Serena cut in, her hurt expression that she acquired during Dan's diatribe quickly fading.

Dan paused. He hadn't meant to say all that, it just came pouring out. "I didn't qualify for financial aid and unless I can find a way to pay my tuition fees…I'm not going to college. That's why I'm a cater waiter."

"Dan, I'm sorry-"

"Serena, being Eleanor's bitch-boy and having Blair ignore me is about all that I can take right now, so please don't pity me. Go sit down, it's okay."

Dan followed her in a moment later, a towel over his arm and a freshly opened bottle of wine in his hand. He began filling the glasses, trying to remain as inconspicuous as possible. When he leant over to fill Blair's glass, the rich scent from her hair hit him and he couldn't help but be aware of how close her was to her. He'd been close to her a lot lately, he knew her scent, her sounds, his fingerprints should be all over her body. And now he could hear her the disapproving clucking of her tongue as she kept her eyes on Cyrus, purposefully disregarding Dan.

"Dan, why are you pouring wine?" Lily asked, even though she had failed to notice when he'd be on her side of the table to fill her glass.

"He's just being helpful. Dan, sit." Serena said quickly, pulling him into the empty chair next to her.

"Of course, Dan it's such a nice surprise to have you here." Cyrus exclaimed in his usual cheerful way. "I suppose it shouldn't be a surprise though, considering how close you and Blair have become."

Rufus raised an eyebrow at him.

"Not close." Blair said, flipping her hair over her shoulder. "We played the lead roles in the school play and I've been helping him with his writing."

"And you're both going to Yale next year." Rufus added.

Dan tried to ignore Serena as she glanced at him. As much as he tried to appreciate her concern, he really wished that she could be more subtle.

"You are?" Cyrus exclaimed. "This is fantastic! Blair, why didn't you say anything?"

"It must have slipped my mind." Blair responded and, this time, Dan did tense up. Serena felt it and immediately let out a scoff as if Blair had just told a joke.

"Like you would forget that Dan - who has been your biggest intellectual rival all through high school – is going to continue to challenge you for the next few years." Serena smiled as she nudged Blair's shoulder. "We all know that this is just how she acts when she's afraid that someone might just be as smart as she is."

"She'll have to get used to that at Yale." Cyrus smiled. "Now where has Corinne got to? It's time for the salt water."

Eleanor cleared her throat and looked pointedly at Dan.

"I can grab that." Dan stood up quickly, grateful for an opportunity to get out of the room.

Rufus immediately looked concerned. "I don't think you should have to-"

"I really don't mind." Dan cut him off.

"You are sort of dressed like a cater waiter." Cyrus said, a smirk playing on his lips as if the notion was absurd.

"I think it's kind of a classic look." Rufus responded defensively.

Dan found Corinne in the kitchen, already preparing to bring out the little bowls.

"Here, let me help you with that." But they both stopped immediately when Blair appeared.

"Corinne, can you take the salt water out please?" She asked, without really asking at all.

"Of course." Corinne smiled politely, then proceeded to leave the room – glancing back to glare at Dan on her way out.

"What are you doing?" Blair spat out the moment they were alone.

"I'm trying to my job." Dan stated as if it were obvious.

"Really? Because it looks to me that you're trying to be two people at once. Are you the cater waiter, Dan? Or are you going to sit down with us for Seder?"

"Like you want me to sit down with your family? You couldn't begin to understand why I'm doing what I'm doing." Dan didn't want to argue with her, but he could feel his blood rising as he ran out of patience.

"You can't be both, Dan! You can't be the cater waiter and a dinner guest. You can't be the lonely outsider, and be friends with Nate and Serena, get published in the New Yorker and be the lead in the school play. You can't be a part of both worlds."

"You mean yours and mine?" Blair swallowed back a retort. "I don't have a choice to make there, do I? Because I'll never be a part of your world. I can be friends with Nate and Serena, get my work published, be the lead in the school play and you'll still always think that I'm beneath you, won't you? Is that why you're really mad? Not because I'm trying to be two people at once, but because you want to keep me you're dirty little secret and you don't like seeing me sitting at your dining room table with your family, right? You're the one who wants to keep our two worlds separate."

Blair froze as Dan stared her down. He had always backed down with her, but he wasn't going to do that this time. She had treated him like nothing since the moment he stepped into her house and, as much fun as it had seemed over the last few weeks, he couldn't handle being in limbo with her anymore. One way or another, it had to end.

"What were we thinking? Things could never work our between us." She finally replied. Dan had his answer.

"Finally we agree on something." And she had his.

"Daniel, we need parsley!" Eleanor shouted from the other room.

"Now if you'll excuse me, I have to get back to my world."

This time Dan didn't sit down with them, he went in, passed the little bowls of salt water around, then walked straight back out again without a word. Aside from Blair and Serena, no one seemed to notice.

"So, you're dating the Waldorf girl, huh?" Corinne asked when he walked back into the kitchen. Apparently he had no safe place to hide.

"No. I'm not. Especially not after tonight." It was almost a relief in a way. Like a weight had been lifted off his shoulders.

"Well, that's probably for the best. I've seen this before you know? There are three types that do it. The teenage girls who do it to get back at their parents, the young women who do it to because they panic one they realize that it's just going to be the same thing for the rest of their lives and the married middle aged women who do it to get back at their cheating husbands."

"Do what?"

"Fuck the help." She said coldly, not even looking at Dan as she prepared the matzah. "It's a phase. It always ends with hushed arguments behind closed doors. But if it's any consolation, a young guy like you won't be lonely for long if you stay in this job."

"There you are." Serena glided into the room, a desperate smile on her face as she tried to make sure Dan knew that she wasn't pitying him. "I told them that you had to take a call, but Cyrus is settling in for another long reading, so it's probably a good time for you to come sit with us for a little while."

"Go." Corinne said, "I can do this on my own."

It was harder this time. It should have been easier, Cyrus was telling the story of Passover, so everyone else was keeping quiet so Dan had no questions to evade. But it was harder. He wasn't listening to anything that had been said, so many other words were going round and round in his head.

Some people have to work….and work and work and then have to work some more to try and get into college

Unless I can find a way to pay my tuition fees…I'm not going to college. That's why I'm a cater waiter.

You'll still always think that I'm beneath you, won't you?

What were we thinking? Things could never work our between us.

Fuck the help.

It's a phase. It always ends with hushed arguments behind closed doors.

"I'm sorry, Cyrus, but…" Rufus suddenly cut him off, "Dan, are you okay?"

Dan paused, he'd been tapping the table with his fingers without realizing, it was a nervous habit that he was generally unaware of – but his dad always noticed.

"I'm fine." He lied.

"Dan, maybe you should tell him." Serena said softly.

"Eleanor's friends are talking during the Seder." Cyrus's mother whined, Dan and the others mostly oblivious to her.

"They're both of our friends, mother."

"Thank you." Eleanor replied emphatically.

"Tell me what?" Rufus asked.

"It's nothing, it's not important. We can talk about it later, okay?"

"Dan." Serena urged him.

"Cyrus, I'm so sorry." Lily said, then turned to Rufus, "perhaps we should go home and talk about…whatever all this is?"

"No, Dan's going to tell me what's going on." Rufus declared.

"If you don't, I will." Serena tried to say softly, like it wasn't a threat. "It doesn't have to be such a big deal."

"Serena, this really isn't any of your business." Dan said coldly.

"Dan," Blair finally spoke, making everyone else silent immediately, "you can't keep this up anymore."

Dan paused. She'd told him to make a choice – but this proved that he never really had one. He now knew exactly what he was.

"I'm the cater waiter." He stated, standing up.

"And not a very good one." Eleanor added scornfully, Dan was surprised that she'd actually been able to keep it to herself for this long.

"Wait, what?" Rufus asked.

"I didn't want you to know, so Serena was pretending that she invited me here. I'm sorry Mr Rose, Mrs Waldorf, I'm very, very sorry."

"Apology accepted." Cyrus said in his usual cheerful tone.

"Hold on, I'm sorry." Rufus stopped Cyrus from getting back to his reading. "Is this you trying to help with college?"

"I know you didn't want me to, dad, but I couldn't do nothing." Dan shrugged as everyone fell quiet. There was nothing else left to say on the matter. "Now, who needs more wine?"

The rest of the evening was oddly easier now that Dan wasn't trying to hide anything. That's not to say that it wasn't awkward, serving his friends and family couldn't not be awkward and it was even stranger when they were all so polite towards him – especially Blair. But Dan couldn't overthink it anymore, it had all become incredibly simple. He was the cater waiter and he was going to continue being one if that's what it took to get into Yale, no matter what other embarrassments he had to endure.

He was halfway through the washing up when Rufus came to say goodbye to him before he left with Lily and Serena.

"You did a really good job tonight." Rufus started, Dan smiled politely at him, but didn't want to go into it anymore. "You know, Dan, I really respect what you're doing, but you don't have to."

"Dad-"

"No, I've been thinking about it and I've decided to sell the gallery."

Dan stopped in his tracks, letting the plate in his hand drop to the bottom of the sink. He was touched, but it wasn't a possibility he could entertain.

"I can't let you do that for me."

"I'm your father." Rufus said, desperately trying to make Dan understand that it was a small sacrifice to make when it came to him son. "I would do anything it takes to help you secure the future that you want."

Dan did understand, but it still wasn't that simple. "But what about Jenny? What about when she wants to go to college?"

Rufus was quiet. Dan knew he had him there.

"I'll figure something out. Dan, I promise you, we will find a way to get you to Yale." He put his hands on Dan's shoulders, empathising the point and letting the moment resonate. Then they let the moment pass. Rufus dropped his hands and stepped backwards. "Do you want me to wait? Give you a ride home?"

"No. I'm nearly all done here, but I'd like to spend some time on my own afterwards. Go for a walk, get some fresh air."

"Okay. I'll see you at home."

Dan didn't say goodbye, he just got back to the dishes and tried to shut off the voice in his head that desperately wanted to leave. To run after his dad and tell him he changed his mind, that he could sell the gallery and everything would work out. That tried to convince him that he could get over the guilt that he knows he would feel.

Twenty-five minutes later, and he was nearly home free. He and Corinne were just taking the last few things down to the van, when Blair appeared in his tracks.

"Can I talk to you for a minute?"

Dan looked to Corinne, she rolled her eyes at him once again that evening.

"Sure." He replied as Corinne turned on her heel, accepting that she'd be doing another task by herself.

Blair waited longer than she needed to to make sure that Corinne was gone, before she spoke. She was nervous, and Dan didn't know what to expect from her now.

"I didn't realize you were doing all this for Yale." She began and Dan saw the pity he didn't want to see in her eyes. Still, he appreciated the fact that she actually cared. "I'm sorry."

"I should have just told you earlier." He replied, rubbing his eyes as he let the defensive exterior he'd been wearing all day finally drop. "I guess I wasn't ready to face the fact that….after working so hard and wanting this for so long and getting in…that it might get taken away from me."

"Couldn't Lily-"

"No, I'm not taking charity. I've come this far by myself and…it's hard to explain. I just can't let Lily pay for it."

"Why not? Are you really going to let your pride cost you Yale? You got in all by yourself, what does it matter who pays for it?" Her softness was gone, but Dan couldn't get mad. He could see in her eyes that her frustration was coming from a good place.

"It matters to me, Blair." He said quietly, hoping it would calm her too – and that maybe, she'd just let it lie.

"Okay. I don't think I can understand it, but if that's how you feel…" She shrugged, then looked around the room like she wasn't sure what to do next. "I'm really sorry, Dan."

"Please don't feel sorry for me, Blair."

"No, I'm not sorry for that." Blair said dismissively, she actually seemed kind of angry at him again, even though she was apparently trying to apologize. She took a deep breath before she continued, "I'm sorry for the way I behaved towards you tonight. I was…shocked…and confused. But that's no excuse. I'm sorry for the things that I said."

"You mean our argument." Dan was stunned. A little happy, but he was still holding onto his anger as well. "So, you didn't mean what you said?"

"Did you mean what you said?" She countered. She was both desperate and confrontational, Dan couldn't tell which emotion was winning out. "Do you think you're my dirty little secret?"

"You tell me."

They both paused. Dan wished he could be a little more mature, a little more rational. He didn't want to pick a fight, but he couldn't just let her stay in her comfort zone forever.

"Look," she finally began to answer, "I'm not ready for all this to be out in the open, but that doesn't mean-"

She paused, her eyes trailing to the elevator. Dan turned to see the reason why. It was Chuck.

"Blair, I need to speak with you." He stated, completely disregarding Dan's presence.

Dan turn back towards Blair, he saw the conflict in her eyes. That was all he needed.

"I was just leaving anyway." Dan turned and walked out without looking back. He didn't need to stay any longer to know where all this would be going next.