A/N: I started watching High Fidelity (didn't finish it, egh) and this just came out. This was also after I read more spoilers about Chuck's girlfriend, so I hope I got it right. Anyway, another post finale fic inside of a normal fic- sorta. You should be forwarned there's underlying Dair just because I think they would be a hilarious couple. Chair will always be my main ship, but Dair is definitely on my list.

Summary: The top five most painful breakups in the history of forever, and she would be lucky to even reach the top ten. Because if he recalled correctly, he might have liked her. But she most certainly never even came close to Blair Cornelia Waldorf.

Disclaimer: Nothing is mine. Influenced by High Fidelity. And I tried to make Chuck's gf as non hateable as possible. (Don't worry, she's there for like a second and then she's gone.) The dates of Chuck and Blair's relationship are taken directly from the show from when the episode aired (I looked it up.) So its as relative to the show as possible.


Eva tossed her long blonde hair and as she walked right out of his life, it occurred to Chuck Bass, her very recent ex boyfriend.

She didn't even make the top five.

The top five most painful breakups in the history of forever, and she would be lucky to even reach the top ten. Because if he recalled correctly, he might have liked her. But she most certainly never even came close to Blair Cornelia Waldorf.

Already sitting in his penthouse, sipping a glass of scotch, Chuck realized that he didn't even need it. His ritual after his significant other would walk out of his door was exactly that.

Give or take a few more scotches. It hadn't occurred to him until that very moment, however, that those instances all had to do with her.

Blair Cornelia Waldorf.

He would have given her more names to emphasize her esteemed essence of he could.

Queen Blair Cornelia Victrola Waldorf III.

Or something just as ridiculous. Because he was sitting after a break up from a different woman and thinking about her. Always, always her.

Vaguely, he wondered if he just rebounded.

Because seriously, Eva didn't even make the top five break ups of all time.

Because they all involved the same woman.

Blair Cornelia Waldorf.

.

Blair Cornelia Waldorf (11/7/07-11/8/07)

Their relationship had lasted three hours, eighteen minutes and ten seconds. Because yes, he really was that good even if it was only her first time. He didn't know when she counted the start of Them or even if she counted those three hours at all.

But he did.

He was sixteen years old and watching Blair Cornelia Waldorf slink up a burlesque stage next to strippers was a sight to behold. It wasn't until she slid into his backseat after stripping herself bare to his utter ecstasy and pressed her lips tentatively did he start the clock.

His first kiss with Blair Cornelia Waldorf was the beginning of their (first) very short time together. From 11:17:07 PM to 2:32:17 AM, she was his. And he made it good for her. Because even though that morning wouldn't have been the most painful play display of her leaving him, that night was the most meaningful. Because without it, Chuck wasn't sure how many more minutes, hours, years, decades that would have passed until he grew jealous enough of her many boyfriends to destroy them, revealing that yes, he had in fact always felt, at least a little subconsciously, for his best friend's girlfriend.

So he did the unethical thing that his morally bankrupt mind urged him to do (as well as other parts of him that weren't his brain.) He took the virginity of one of his best friend's and his best friend's girlfriend and he liked it.

He said he was morally bankrupt.

She knew it too, which was why it didn't seem like such a big deal when she pulled her slip back over her head with a simple eye roll and a dry "thanks." And by exiting that limo she had ended their three hour, eighteen minute, and ten second relationship.

He stared after her indifference that so matched his and knew something terrible had happened. He looked after her, knowing his heart had just broken.

If only a little.

He just didn't let himself accept it until the following day.

"The memory of last night will never be mentioned again, is that clear?"

"Not as clear as the memory of you purring in my ear which I have been playing over and over."

"Well erase the tape. Because as far as I'm concerned it never happened."

It wasn't the most heartbreaking of her breaking his heart, but it was one of the most important. Because he realized that he was slightly in love with the only girl he ever would be after staking her virginity as his own.

What a bitch.

.

Blair Cornelia Waldorf (11/8/07-12/5/07)

A month. Barely a month. They were off by about three days.

27 days they were together. Some might not consider sneaking around with your ex boyfriend's best friend a relationship, but he sure as hell did. He did because he suddenly found himself actually caring about a girl. He cared about her thoughts and opinions. He cared when she cried that her mother had scared her daddy away. And he was scared when he would find her curled in on herself on bathroom tiles because she was just too beautiful for that.

He had suddenly found himself desperate for her to allow him to take her to her Cotillion and it was in that frightening moment did he think something even worse had happened than liking her. As he watched her prance around on the arm of Princess Theodore, he realized that he had to destroy that. And when Nate came along, he had to destroy that as well.

Carter Baizen had just been a pawn. But fear quelled within him as she seethed with anger, wrenching herself away from him.

"You make me sick."

"Blair, wait. I didn't mean-"

"This thing between us. It's over. For good."

It wasn't the first time she would say those words to him, but it was one of the most painful. Because it was the first time. Oh, Fate. What a clever bitch.

He didn't know what he was doing but suddenly he was in a hotel in Monaco and he knew that bitch had broken him. He hated her and wanted to to slide between her thighs all at the same time.

That bitch had broken him.

And he loved her.

He never slept with the same girl after one night but there she was, dominating his thoughts. She made rage and jealousy claw at his insides. She made him betray his own best friend and still the only thing he could think of was those wide brown eyes that could look so innocent yet cause nations to fall.

It wasn't the worst break up but it was the most jarring because he wasn't prepared for it. He didn't know what it was, that such pain could even exist. At his father's wedding he would look in disgust at his new sister and her tears but he didn't take it for granted.

Just because no one understood it, didn't mean that it didn't hurt that much.

And because Blair had just walked up to him in that little pink dress of hers and he liked dancing with her.

.

Blair Cornelia Waldorf (5/25/09-4/5/10)

Almost a year. They could have lasted a year if they only lasted a month a twenty days more. But they had to break. He just had to screw up. Like he always did. Because he proved his father wrong by keeping his hotel, but he proved him even more right by losing the one thing that really mattered.

It may have seemed as though his stints with Blair Cornelia Waldorf would only get longer with time. Maybe next time they would last two years. And then a decade. And then maybe more. But that sting across his cheek paled in comparison to the empty ache in his chest that would never go away.

Not ever.

Not until she would come back to him. Because she had to.

She just had to.

There really wasn't anything more to say than that.

"Goodbye, Chuck."

That wasn't the last time she would say that to him.

It wasn't the worst break up because there was no way in hell he was giving up that easily. No matter how much he hated himself.

.

Blair Waldorf (4/12/10-4/12/10)

He couldn't remember the number of times he had called her.

It was a lot.

And even saying that was an understatement. He was sure he was drunk for most of them because all he could think of were dial tones. It was hard enough that the morality twins would come around with their shiny hair and oblivious looks. Because they didn't know. They didn't know really. They didn't know about him and Blair Cornelia Waldorf. They never did. No one did.

It was hard enough sleeping through his film-noir dreams. All he dreamed of was her and the things he had done to her. All he thought of was her. All he drank, ate, and breathed was her.

Always had been, always would be. There was no other way. He didn't know how to live when she wasn't living it there with him.

So he screwed up. She looked at him with those hateful eyes of hers and he knew he would love her until his last breath.

So he called her in his drunken stupors because he didn't know what else to do. He didn't know how else to be without her. Before were just petty arguments about who slept with who and who left who at what helipad.

He had ruined her.

But she couldn't leave. Not now. Not ever.

It wasn't Nate's urging or Serena's innocent eyes.

It was only a matter of time before he broke.

He hated the disgust in her eyes but he hated even more her distance from him.

"Our pull is as undeniable as ever."

He supposed it was too easy to get her back with him again. It was pure logic which was just illogical. It was easy to pretend when she was in his arms again. He would press a loving kiss to her soft hair and it was easy to pretend that she still loved him. Because she was with him again.

He just wanted her so desperately to be in his arms again.

But it wouldn't last.

It barely lasted 12 hours. He couldn't recall. All he heard was her leaving him for the second time that week.

"We have to see this through until the end."

"This is the end, Chuck."

He hated the way she said his name as she walked away. He hated the tears he caused run down her face and he definitely hated that brunette Russian chick he had to bang so he could pretend some more.

Because she was dancing with Humphrey and if she let him touch her, he would kill the bastard with his bare hands.

It was the second worst. Because for that heart wrenching month, he almost let himself believe that she had stopped loving him.

.

Blair Cornelia Waldorf (5/17/10-5/17/10)

He heard her call out to him and he should have been petrified that she would discover heartbreak all over again. But all of that fear melted away and was overshadowed by her simple and perfect appearance in his house, holding peonies and he knew that he would marry her some day. He would make her his wife. The way it should be.

Five hours.

Maybe.

That was how long their reconciliation lasted. He knew he couldn't lie to her. He knew he couldn't hide it from her. But he knew she would slap his face twice as hard when she found out. So he had to prolong it as much as possible. Because there was a box in his pocket and he needed her.

God, he just needed her.

He kissed her furiously and sweetly, hoping he could convey enough that she was all he needed. All of his past mistakes meant nothing. She meant everything. He needed her to stay with him.

He was nervous.

It was something he was unaccustomed to, but when it came to Blair Cornelia Waldorf, he really shouldn't have been surprised. She made him feel things that he never should have. And she did it with a surreptitious smile and well hidden seduction that he could still feel reverberating from three years in the past.

He wanted everything to be perfect. So he could propose to her. His heart was thrumming and he knew he had to get music to shut the hell up or it would all just spill out of him like a command.

Marry me, Waldorf.

He hoped she would have said yes.

Instead, he pulled out that box in the middle of a hospital. It wasn't right and it wasn't perfect because suddenly Humphrey's fist collided with his jaw and he knew this sad Brooklyn resident had been created just to destroy him.

It wouldn't have been the first time.

"Will you-"

was all he got out. And she was crying again and screaming and this was definitely the worst thing he had ever done.

"I thought you didn't love me anymore. I didn't care if I lived or died."

It was the truest thing he had ever said to her because he was laying in a pool of his own blood and he almost laughed at the truth of it.

He would love her until his last breath.

Lying in a pool of his own blood, he knew this was the worst. Because this time, Blair Cornelia Waldorf really had killed him.

.

Chuck didn't know how much longer he was going to have to take this. He watched her with her convincing innocence and her underhanded smiles (and if Humphrey got even closer to her he was going to lose it.)

"You can stop staring."

At least it got her attention.

"I could," he ventured. "But then who would shamelessly oggle you because you gave your virginity to him in the back of his limo?"

"Humphrey?"

Now she was just talking to make him mad.

Her smile was precious and devious and he wanted to kiss it.

But he couldn't. He still wasn't good enough for her. So he would shamelessly oggle her until his last breath (again) because there was no way in hell she was taking him back. In fact, he was pretty sure that would be the only place she would let him touch her again.

"So are you ever going to tell me?" she finally asked after a moment.

"What?"

But he had a feeling that he knew.

She rolled her eyes impatiently. "Really, Bass? I perfected that coy act."

He just stared at her harshly, daring her to say it.

"Were you ever going to tell me you got shot?"

"Were you ever going to take me back?"

"Were you ever going to stop whoring yourself out to any pretty girl who would look at you?"

"You would know."

They stared at each other harshly, both being more stubborn than the other.

"Do you want me back or not?" Blair asked.

"What?" he asked in surprise. He wanted to give her a sharp don't flatter yourself but knew it was better this way. Instead he gave her a, "what do you think?"

"Excuse my confusion," she said and it hit him straight in the gut, "but you trolling around with nice girls from France doesn't really send the most concise message."

"Have I ever wanted anyone but you?" he asked.

"Yes," she said instantly.

"Then I guess it worked."

"What worked?" she asked sternly.

"My act," he smiled.

"Don't you dare smile at me like you've won already, Chuck Bass," she snapped. "Because, News Flash: I'm still mad at you."

"That doesn't surprise me," Chuck answered.

"Good."

They were staring at each other again and he definitely wanted to kiss her again.

"I'm still mad at you," she reminded him again.

"I know," he said, self consciously looking at the ground.

She wished that she didn't find it so damn adorable.

But she was still mad at him. Damn bastard got himself shot and didn't tell her.

And the Slut-That-Shall-Remain-Nameless debacle. But it still wasn't as bad as being pimped out by your boyfriend to his uncle.

Even if it still did hurt.

"Get that ring and we'll talk."

Chuck looked up in surprise.

"What?" he asked. He wasn't being as eloquent as usual.

"Don't think I don't know what was in that box," Blair said. "And don't think that I don't know the reason you almost died in Prague. It was the only reason that I didn't tear her stupid blonde hair out by the roots."

She could be so beautifully awful when she wanted to.

"Blair Cornelia Waldorf in a cat fight," Chuck murmured.

"You're lucky she was so nice or I really would have hated her," Blair remarked. She liked how he said her name like that.

"She served her purpose," Chuck replied. He needed her to know that this girl was just as nameless and faceless as the others. He liked her well enough and yes, she was nice. And that was the point. And just needed Blair to see.

They could be together. This time, he wouldn't let them break apart.

"There must have been other reasons," Blair said suggestively.

"Well there wasn't," Chuck snapped angrily. That she would even insinuate that Eva could mean more, even sexually, was something that he couldn't comprehend.

"That was it, then?" Blair asked dubiously. "Come on, Bass."

"What?"

"Getting some French girl to try and make me jealous?" she scoffed. "I pulled that two years ago and it didn't work then either. You're going to have to do a lot better than that if you ever want to marry me."

He tried to ignore the tightening within him at those last two words.

"I wasn't trying to make you jealous," he uttered. "I was trying to..."

"Be a better person," Blair rolled her eyes. "Yeah, I don't care."

He looked back into her face and he knew the exact reason why he could never love anyone else. She was caviler and she was blasé and she was meant for him.

No one could ever know him the way she did. And she saw right through him.

"Next time you go and get shot, don't get a personality check," she told him. "Watching you become a humanitarian was nauseating."

"I thought it was what you wanted," he answered. Her eyes narrowed and she sort of wished she hadn't done this to him. If it wasn't for her, he wouldn't have been an idiot and gotten drunk in Prague's version of the Red Light District.

Idiot.

"If I wanted a sickening display of humanitarianism, I would be dating Humphrey," Blair said. "Or worse. Vanessa."

"Now there's a thought," Chuck remarked coolly.

"I told you I'm not done being mad at you," Blair said pointedly. "Don't talk to me like we're friends again."

"How do you want me to talk to you?" Chuck inquired. "You've already reprimanded me for pretending to be someone I'm not."

"I never said you didn't have to have even an ounce of humility," she responded.

"But that's not me," he shrugged.

"Yeah, and going out to make yourself a better person isn't you either," she said sharply. "Maybe that's why she left you. She saw how fake you were being."

"She didn't."

"What?" Blair asked.

"She didn't leave me," he repeated. She crossed her arms over her chest, observing him closely.

"This isn't a game," he told her, reading her mind. "I told her I wanted to marry you. She wasn't that surprised."

"And she just walked out of here," Blair said.

"I told you," Chuck said. "She wasn't the surprised. She knew the minute that she saw you."

Blair paused. "Yes...?" she prodded.

"That I was in love with you," Chuck answered begrudgingly. Personality check or not, he was still paranoid of saying those words when they weren't together. "I don't suppose it was that hard to spot."

"Stop trying to get on my good side," she warned.

"I didn't even attempt to flatter you," Chuck defended. "It's just the truth."

"Well stop it," Blair said. "It's hard being on guard all the time. There's no telling what you might try."

"I might try to marry you," he offered with a smirk.

And there was her Chuck.

"Let's see you work a little more for it, okay, Bass?" Blair asked, arching a dark eyebrow. She turned away from him and he just knew it.

He was going to marry her whether she liked it or not.