A/N: I spent two days on this chapter. I have been through more than ten drafts and this was the frustrating result. To be honest, I am still not satisfied with what I have written. I blame the lame and time-consuming defensive driving classes I have been taking for the past two days.

Wake Up To The Breakup


Jenny sneaked into the penthouse as quietly as she could. She was still slightly in shock over what she had seen about an hour ago. She had stayed overnight at Eleanor Waldorf Designs to work on her debut fashion line and had left promptly in the morning only to see something that she wished she hadn't. Blair Waldorf had strode out of Chuck Bass's house that morning looking very much smitten with the boy in question and he had undeniably had the same sparkle in his own eyes. At first, Jenny had tried to convince herself that what she had seen was merely a figment of her imagination, but the kiss the pair had shared in the end had only served to confirm her suspicions rather than denounce them.

The mix of emotions that she was currently experiencing were troubling to say the very least. On the one hand, she was genuinely happy that Blair had discovered that special connection with someone again because whether Blair would admit to it or not, the brunette had lost that very connection with her brother for quite some time now. On the other hand, Dan was her brother and his heart was about to be inevitably broken.

Jenny poured herself a glass of orange juice and took a seat on the couch still clearly deep in thought over what she had had to witness that morning. Should she inform Dan about what she had seen or should she keep this secret safe for Blair until the brunette broke up with him herself? Jenny knew that Blair would never want to hurt Dan intentionally. Surely the brunette was planning to break up with her brother very soon. The blond trusted that she would do the right thing eventually. What if she had simply misinterpreted the situation? Then again, how could one possibly misinterpret a single kiss? These questions continued to swirl around in her head unanswered until her thoughts were interrupted by Rufus, who had finally woken up to greet the beautiful morning.

"Good morning Jen," he greeted her as he poured himself his usual morning cup of coffee. "Did you have a nightmare sweetheart? You seem a little dazed."

She smiled reassuringly at her father and said, "I did have a nightmare of sorts, but I'm fine."

Rufus brought his steaming hot cup of coffee with him and sat down next to his daughter on the couch, his forehead evidently creased with signs of worry and obvious concern.

"Do you want to talk about it?" he urged. "You'll feel better if you talk about it."

Before Jenny could decline his offer, Dan strolled into the kitchen and greeted them both groggily. Jenny returned his greeting with a weak smile as Rufus bade his son good morning and continued to observe his daughter in utmost concern.

"You seem a little dazed," Dan commented at Jenny, echoing the deduction that Rufus had made moments earlier. "Your fashion line not coming along too well?"

Nothing ever got past the Humphrey men, especially not where Jenny was concerned. They both cared about her too much to miss a beat.

"I just had a nightmare last night is all. Dan, may I please speak with you in private?" Jenny requested, glancing at him insistently to let him know that he really had no choice in the matter.

"Sure Jen," he answered uncertainly, cocking his head towards the stairs.

Jenny placed her empty glass in the kitchen sink and followed her brother up the stairs just as Rufus called out to stop them in their tracks.

"Hold on a second," Rufus insisted, motioning for his children to backtrack in their steps.

The two Humphrey children paused instantly, turned around, and waited patiently to hear what their father had to say.

"I know Dan doesn't have class until noon today, but you're going to be late for school Jenny," he reminded her.

"I'll walk you to school then," Dan offered. "We can talk along the way."

Jenny nodded her head in agreement over the proposed arrangement and grabbed her purse before the two headed out of the penthouse. Rufus watched his daughter's retreating figure from the window as a frustrated sigh escaped from his lips. He trusted that Dan would let him know if anything serious was happening with Jenny. His fatherly instinct was certain, however, that what was bothering his daughter was more than the simple nightmare that she had pinned it to be.


"So," Dan started casually the moment they had stepped outside.

Jenny wrung her hands in anticipation and blurted, "Blair is cheating on you with Chuck."

Dan stared at his younger sister in disbelief for a moment before letting out a tiny chuckle.

"You almost had me going there Jen," he told her.

"Dan," the blond insisted. "I'm being serious. I saw them together this morning with my own eyes. She was leaving his house and..."

"Maybe she was there as a part of her investigation of Pete's murder," Dan interrupted her immediately, unwillingly to believe that Blair would be unfaithful to him.

"They kissed Dan," she insisted. "I'm sorry, but..."

"But what?" he questioned, interrupting her unwelcome words once more. "Are you one hundred percent certain of what you saw Jenny? I mean, Eleanor has probably been forcing Blair to spend more time with Chuck, you know? Maybe Blair thought I would get upset if I found out about it, so she refrained from telling me about her meaningless meetings with Chuck."

"I know what I saw Dan and besides, Eleanor is still in France. Even if she has been demanding that Blair spend more time with Chuck, why would she continue to do so the moment her mother was out of town?" Jenny asked him. "You and I both know she would disregard her mother's command in her absence. That is if she hadn't done so already in her presence of course."

"Well, the angle you were watching them in could have made it seem like they were kissing when they really weren't," Dan offered, ignoring her most recent retort. "I've seen that happen in movies plenty of times."

"I'm sorry Dan, but I know what I saw and I definitely saw a kiss," she persisted.

Dan racked his brain for another excuse to pardon his girlfriend from the situation Jenny had caught her in that morning, but unfortunately, drew a blank.

"Thanks for telling me Jen," he said instead as the two neared her school.

Jenny gave her brother a tight but awkward hug and reiterated, "I really am sorry. I know you've been planning to propose..."

"I need to be somewhere," he disrupted her train of thought. "Thanks for telling me again Jen. You did the right thing. Please keep this between us for now."

He started to walk away then and as much as Jenny wanted to stop him in his repetitive movements, she knew better than most people that he desperately needed to be left alone. A broken heart was a dire condition that was better suffered alone in her limited experience. It was only when you finally overcame the pain and the hurt and chose to pick up the shattered pieces of your broken heart that a helping hand would truly be appreciated.

Jenny flipped open her cell phone almost immediately after her brother's departure and dialed for Vanessa. After all, she was his best friend. Dan had told her to keep this between them for now, but surely Vanessa was an exception to his demand. Jenny trusted that the raven-haired girl would be there at the right time and place to pick up the pieces of Dan's broken heart.


"Chuck!" she scolded him openly. "What are you doing here? I thought I told you..."

"I know," he assured her as he closed her bedroom door gently behind him.

"Chuck!" she reprimanded him again. "Did anyone see you?"

"It hurts that you doubt my skills Blair," he scoffed as she rolled her eyes. "I was totally stealth in sneaking in here to talk to you."

"Seriously Chuck," she started as she put the finishing touches on her makeup. "What are you doing here? Dan is waiting outside for me for our anniversary date."

"Are you really going to tell him about us tonight?" he asked her for confirmation.

She nodded in affirmation.

"I was actually planning to tell him earlier. I figured the sooner I told him, the better, you know? This isn't fair to either you or him," she announced. "He was unreachable all day though. I'll tell him as soon as possible. I promise."

It was his turn to nod solemnly, although a tiny smile exposed itself at her words. This isn't fair to either you or him. There was something about the knowledge that she was thinking of him as well that caused the butterflies in his stomach to flutter at their own accord.

"Blair, I think we should tell him together," he suddenly suggested.

"Are you crazy?" she asked him, although the answer was as clear as day to her.

"Eric and I went to pay our respects to our mother after we parted ways this morning," he explained.

She took his hand in hers upon instinct and gave it a light but reassuring squeeze. He smiled gratefully at her comforting gesture and continued.

"It was liberating," he insisted. "When we left, however, Eric mentioned something that really had me thinking."

"What did he say?" she wondered curiously, pressing her lips together into a thin line.

"I'm the other man," he stated simply.

"Yes," she agreed hesitatingly, confused as to why he was insistent on stating the obvious.

"I'm the other man," he repeated as he ran his free hand through his disheveled hair. "Eric made me realize how much of a hypocrite I really am."

Upon hearing him label himself as a hypocrite, Blair finally caught on to where his concerns lay.

"So, I would be the equivalent of your mother in this scenario," Blair said, stating the obvious exactly as he had moments earlier.

He sighed and shrugged off the hold she had on his hand.

"I think the least I should do is apologize to him for what has transpired between us Blair. It's just as much your fault as it is mine; it's just as much your responsibility as it is mine," he reminded her.

There was a brief silence before Blair spoke up again.

"I know what you mean Chuck, but I think I should settle this with him by myself first," she voiced her opinion. "He'll probably need some space after our breakup as well before he'll even consider listening to what you have to say."

Chuck sighed again, but this time, it was in defeat.

"You're right. I just felt so guilty after what Eric had pointed out to me that I felt complied to do something on my part, you know?"

"Yeah, I know," she assured him, resting a hand on his shoulder. "I really have to go though Chuck. I'll call you later."

With that final farewell, she left him sitting in her room pondering over the mess of a situation they were currently in. He continued to hang his head in shame even moments after Blair had left. He was such a fucking hypocrite.


Blair approached the limo cautiously and took a deep breath to help calm her nerves. She had practiced what she would say to him over and over again in front of the mirror before Chuck had caught her by surprise and nothing had sounded quite right. She hoped winging this would turn out for the better. He stepped out of the limo then and she offered him a weak smile.

"You look beautiful Blair," he breathed as he helped her into the limo. "Happy anniversary."

"Happy anniversary," she echoed upon instinct.

She paused immediately afterward over what she had said as her guilt began to consume her.

"Dan," she started, her unsteady voice betraying how nervous she really was. "I need to tell you something."

Dan smiled and said, "Wait until we get to our destination alright? Here, I'll help you put on the blindfold."

"I'm so sorry Dan," Vanessa told him as he left his afternoon class.

"What are you so sorry about?" he asked in confusion, walking side by side with his best friend down the narrow hallway.

"Jenny told me about Blair and Chuck," she answered testily.

Dan smiled easily in her direction and shook his head to erase her words from his mind.

"Vanessa, I still refuse to believe that she would cheat on me. Today is our second year anniversary. Unless I witness or hear her confess to the affair myself, she is still very much the loyal girlfriend I know her to be and I still very much plan to propose to her tonight."

"Dan," Vanessa urged. "I really don't think that's..."

"My decision is final Vanessa," he told her confidently. "I trust her. I know her character. She would never be unfaithful to me. I haven't given her reason to be. As my best friend, I need you to support me in my decision."

"Dan," Blair tried again, cutting through the memory. "I really..."

His heart continued to insist that what she had to say would have nothing to do with ending their relationship or Chuck. His mind, however, was screaming for him to wake up from his idealistic thoughts. He ultimately chose to listen to his heart, interrupting her once more.

"Please?" he insisted, his face filled with anxiety.

Blair didn't have the heart to tell him about her and Chuck then, so she merely nodded her head as Dan put the blindfold over her eyes.

"Dan?" Blair asked uncertainly as she was guided out of the limo. "Where are you taking me?"

"You'll see," he whispered as he led her into the restaurant.

He lifted off her blindfold moments later and Blair gasped at the scene before her. There was absolutely no one in the restaurant but them and the atmosphere was undeniably radiating with romance. A red tablecloth had been chosen for the table. Candles were lit all over the restaurant and there were even red rose petals adorning the floor. Blair wished Dan hasn't put so much thought into their anniversary date. It would have made what she was about to say so much easier.

"Dan," she reminded him. "You said I could say what I wanted to say the moment we got here."

Dan smiled and replied, "I know, but hang on for just one more second alright?"

Before Blair could protest, he ran off into the kitchen, the swinging doors being the only sign that lingered of his recent presence. She wrung her hands in anticipation over his return as she went over her plan on how to break the news to Dan. When he finally did, he was followed by the entire kitchen staff, who set down a sea of delectable dishes before them. Blair felt guiltier and guiltier by the second. They were all of her favorite dishes.

Dan handed her the fifty red roses he held in his right hand and said, "These are for you and I actually prepared these dishes all on my own. I've been in that kitchen cooking since I got off my afternoon class, which is why I haven't been answering any of your calls. I made the hot dishes last of course and that's why I was rushing to get you here – because I didn't want the food to get cold. Oh and the entire staff have tasted the food themselves and have given this meal their stamp of approval. I promise you that you won't get food poisoning of any sort and I also..."

"Dan," she tried adamantly to interrupt his rambling.

Dan always rambled when he was nervous and this made Blair feel even more sick at what she was about to do.

"Yeah, alright," he responded, finally taking his seat at the table after having pulled out her chair for her to be seated. "You're probably hungry. Happy anniversary Blair."

"Dan," she urged. "I really need to talk to you."

He finally dug up the courage to look her in the eyes and nodded for her to proceed with what she had to say.

"Sure," he agreed. "I'm all ears. Is everything alright Blair? You look kind of pale."

"I'm fine," she managed to choke out. "Dan, I don't know how to say this and I'm sorry for bringing this up at a time like this, but I really don't think it's fair to you if I drag this on any longer."

"Are you breaking up with me?" Dan whispered in disbelief, uncontrollably voicing what the logic of his mind had been trying to convince him would happen all day. "Was it something I did? Was it something I said? Is it the food? It's the flowers, isn't it?"

He was rambling not because he thought it was actually any or all of those issues that had led her to break up with him. He just didn't want to hear her real reasons for doing so afraid of what they might be. He feared that what Jenny had seen that morning was exactly what she had deduced it to be and that Vanessa had been right in advising him not to propel forward with his proposal tonight.

"Dan," she sighed. "Please."

He nodded and stopped talking, dreading for her to finish what she had to say. He had no idea how he would be able to handle it if he heard her mention his name.

"Something has been going on between me and Chuck," she whispered truthfully, her head hung low in shame. "I'm sorry. I..."

She had said it. She had finally said it and all Dan felt was the unexpected feeling of desperation coursing through his body. He was desperate to refute her confession. There had to be some mistake. He was so distraught to finally hear it from her that he just started offering the very excuses he had made for her in front of Jenny earlier in the day.

"Is it your mother?" Dan clarified. "Is it because she's been pressuring you to be with Chuck instead of me?"

"No," she told him. "It just happened Dan. I..."

He felt his heart shatter at her insistent words, but he stood by his theory. Blair loved him and he loved her. How could it be possible that she would willingly cheat on him and leave him like this?

"Blair," he said, taking her hand in his. "You don't have to lie to me. We can get through this together. We love each other. We can't let your mother tear us apart like this."

"Dan!" Blair shouted before lowering her voice once more. "What happened between me and Chuck had nothing to do with my mother."

"Then what happened Blair? How did we get to this place?" Dan asked restlessly.

His mind was spinning out of control. This had to be a nightmare. He pinched himself to be sure, but found that the scene before him had failed to fade away.

"We just kissed a few times and I swear I wanted to tell you about each of those incidents, but I just..." she trailed off when she noticed Dan's eyes starting to glaze over in silent fury.

"You just what Blair?" he spat.

Finally the anger had kicked in like it should have a long time ago.

"I'm sorry. One thing just led up to another and..." she started.

"Did you sleep with him?" Dan questioned, his eyes boring intently into hers.

She nodded numbly at him as Dan turned away from her to hide the tears that threatened to fall from his already glistening orbs.

"Yes," she whispered in verbal confirmation and Dan laughed at the irony of the situation.

That word was supposed to have made him the happiest man alive tonight and yet his whole world had just shattered at that very same word that had just escaped from her parted lips.

"Willingly?" he choked out.

That one last question represented the one last shred of hope within him that he could possibly salvage their relationship. If Chuck had forced himself on Blair, he would kill him. She nodded again though to his dismay and he felt the ground beneath him give way under his heavy weight. Actually, he wished it had. He got up and started to walk away from her when he heard her calling his name.

"Dan," she reiterated for the millionth time. "I'm sorry."

He let out a pitiful laugh, but still refused to turn around and face her.

"You know Blair? I wanted to propose to you today. Even when Jenny told me about seeing you with Chuck this morning, I convinced myself that she was just seeing things. I booked the roof at Victrola and decorated it just like I had with this restaurant. I am such an idiot! I even had a backup proposal plan just in case anything went wrong! Vanessa practically told me I was being stupid for thinking otherwise, but I stood up for your character Blair. I stood up for us. I informed them both so fucking confidently that you would never cheat on me Blair; that we loved each other."

"Dan, I didn't mean for you to find out this way," Blair insisted, tears brimming in her own eyes.

She did love Dan and seeing him so hurt broke her too.

"Right," he shot back sarcastically. "Because you tried so hard to be honest with me Blair! Why not have the best of both worlds, right? Have your doting boyfriend continue to act like an oblivious fool and screw your hot detective on the side too! Why the hell not?"

"It wasn't like that Dan!" she yelled. "It just happened ok? You think I don't feel bad about this? I tried to ignore what I felt for Chuck because I thought it was a fluke too at first, but I just couldn't in the end. I didn't want to hurt you. I thought about telling you about us numerous times. I've been calling you all day to try and tell you the truth."

Dan remained silent and all that could be heard were the sounds of Blair's hitched breaths being fueled by her uncontrollable tears.

"We're done," he whispered harshly. "I never want to see you again Blair."

With that, he stalked out of the restaurant as the staff continued to eavesdrop from behind the kitchen doors. I never want to see you again Blair. His words continued to echo through her mind and the truth was that she didn't blame him in the least bit. She was such a hypocrite – in the same way that Chuck was. Maybe they did deserve each other. She had hated Robert for cheating on her with Serena in high school. Blair had been adamant that there were absolutely no excuses for cheating and then keeping it from your significant other. Yet here she was committing the very act that she had alienated Serena and Robert for.

She was such a horrible person. What had Dan seen in her? What did Chuck see in her? She glanced over at the plates of food before her that had yet to be removed and began to dig into their contents in a hurried effort to numb her pain. Bite after bite she dug her fork in. Bite after bite she had to force the food down. Bite after bite she felt more disgusting and she was. She was absolutely disgusting.

She ran into the bathroom and did the only thing she could. She stuck her finger down her throat repeatedly and was only satisfied when her stomach was entirely empty. Her cell phone began to ring relentlessly then. She stared at her sounding phone for a minute or two before she chose to ignore the call completely. Blair stood up from her position on the floor, steadying herself by placing a hand on the porcelain bowl, only to crumble soon after against the tiled floor.