Shortly after she graduated from Columbia, Blair became engaged to her boyfriend of nearly eight months, Trip Vanderbilt. The Vanderbilts were one of the few families that could compare with the Waldorfs in terms of history and prestige and Trip was a well-respected up and coming politician.

On one of the first weekends of the summer, Blair and Trip held their engagement party. The party was filled with all of the most elite members of Manhattan's Upper Eastside. Blair had hoped that the announcement of her engagement would serve as her introduction as a respectable, mature adult and not just Harold and Eleanor's granddaughter.

But unfortunately for her, there was an unexpected guest who did his best to ruin her plan.

About halfway through the party, Chuck came sauntering in, having already consumed a few glasses of scotch before he made his appearance.

He strolled up to Blair, who was talking to a group of her grandmother's friends, with Serena and Nate trailing behind him to make sure he didn't cause too much trouble.

Blair saw the startled looks on the older women's faces and she turned around just as Chuck reached her. She excused herself from women and addressed Chuck with her hands on her hips, "What are you doing here, Bass?"

He smirked lazily, "Why, to give my congratulations to the happy couple, of course."

"Chuck…" Blair said warningly as Trip came over to join them.

"Blair, is everything alright?" He asked as he put an arm around her waist.

Chuck's eyes focused on Blair's hip where Trip's hand lay and his smirk quickly faded, "Ah, just the man I was looking for." He said sarcastically.

Trip glared at him, "What are you doing here, Bass? I know for a fact you were not on the guest list."

Chuck rolled his eyes, "Like that would ever stop me." A cocky grin formed on his face as he continued, "I just came to tell you what a lucky man you are. You really got quite the catch here."

"I know." Trip said as his grip on Blair's waist tightened.

Chuck's eyes flashed with anger for an instant, but his sneer remind in place, "I mean, she's beautiful, smart, and not to mention a complete tigress in bed." He looked her form up and down and his grin only grew as he saw Trip's hand clench in anger. He broke his gaze away from Blair and turned his attention back to her fiancé, "But I just thought I should let you know that when it comes to pleasure of the sexual nature, I taught her everything that she knows. So remember that every time the two of you consummate your relationship, she can't help but think of me."

Trip took a threatening step forward, "Shut your mouth you little-"

"Okay, that's enough." Serena said quickly as she stepped between the two and Blair grabbed Trip's arm to restrain him.

At the same time, Nate got a hold of Chuck, "I think it's about time you left, Bass." He said he began to lead the younger man out of the room, "You need to sleep off some of that alcohol. You reek of scotch."

Chuck scoffed as he momentarily pulled himself out of Nate's grasp. He turned back towards Blair and Trip, who were both glaring at him darkly, and bowed slightly, "Congratulations, again. I'm sure you'll enjoy many years together in your cold, loveless marriage."

Trip's face was red with fury and Blair's mouth was open in shock and embarrassment as Serena went and helped her boyfriend lead Chuck out of the room, "Okay, that's about enough out of you," she said as they walked, "You can't say just say things like that."

"I'm Chuck Bass," he drawled, "I can say whatever the hell I want."

Serena rolled her eyes at his attitude just as they reached the lobby of the building where the party was being held.

"Get off of me," Chuck grumbled as he shook off Nate's hand, "I can walk on my own. I'm not that drunk."

Serena opened her mouth to argue, but before she could get a word out, they all heard the ominous sound of stilettos storming purposefully along the marble floor. The three young people turned to see a very angry Blair Waldorf enter the lobby and stomp over to where they were standing.

"You heinous Basshole," She hissed as she slapped him across the face, "I can't believe you did that! You caused a huge scene. Are you happy now?"

"The real question is, are you?" He asked as he rubbed the quickly forming red mark on his cheek.

"What?"

He gave her a withering look, "Trip is everything you ever wanted when you planned out your perfect life. He is your perfect, little prince, and best of all, he has somehow managed to win over both your parents and your grandparents. You must be thrilled." He said sarcastically.

"What are you implying, Bass?"

"I think you know," Chuck said darkly, "You don't love him, but it doesn't even matter to you. What is important is that everyone else loves him. Your family, your bitchy little friends, the adoring public, they all approve and that is exactly what you were looking for, wasn't it?"

"Please," Blair scoffed, "You don't know what you're-"

"Yes," Chuck cut her off, "I do. Because if you wanted to be with someone you loved, you would be with me. I know you still love me, Blair. I know you always have, and you always will but as long as you can find one person who doesn't like us together you will continue to keep us apart."

"You are so conceited," Blair said, trying to remain cool and indifferent. But Chuck caught the vulnerability that flashed in her eyes and he knew that his words were getting to her.

He tilted his head and held her gaze with his as his voice softened, "Why don't you just do what you want for once? I know you want me. Why won't you just let yourself be happy?" He asked as he stepped closer to her.

Blair's mask fell away and the tears welled in her eyes, "It's not that simple."

"Why not?" Chuck sneered, "Explain it to me."

Blair shook her head sadly, "You don't understand. I didn't want to break up with you. I never wanted to, but I had to. I didn't have a choice."

"What do you mean you didn't have a choice? Of course you did."

"No, I didn't. My grandparents told me that I had to pick, either you or them. Either I ended things with you or they were going to cut me off completely. No trust fund, no parties, no Columbia." The tears began to fall down Blair's face as she explained, "Don't you see? I would have lost everything. There was no other option; I had to leave you."

"No." Chuck shook his head before he looked up at her angrily, "You could have picked me. I would have taken care of you. I may be new money but everyone knows my father has as much, if not more, money as your grandparents and I would have married you in a heartbeat to make all that is mine yours. You knew that, but you made your choice because it provided you with the opportunity to do what had been in the back of your mind for a while. You wanted an excuse to end things. You couldn't handle the fact that there was so much disapproval surrounding our relationship, and your grandparents gave you the perfect reason to end it."

"No," Blair said through her tears as she shook her head, "I wouldn't-"

But Chuck ignored her and continued his rant, "I was caught off guard that night, but the more I thought about it, the more I realized that I knew it was coming. You have been trying to get your family's approval since we were kids. You want to be what your parents want and what your grandparents want, even though those two goals do not overlap in anyway. But they both could agree on one thing, right? That I'm no good?" He chuckled bitterly, "Their hatred for me and my father was the one thing they could see eye to eye on, and since you put so much value on what they think, I knew that as long as they both wanted me out of your life it was only a matter of time before you did what they wanted."

His face became earnest, "When are you going to get it, Waldorf? You're never going to make them happy. You've always tried to be perfect for them; to do everything they wanted from you, and they just keep wanting more. Don't you see? You got perfect grades, you got into the perfect school, you are going to marry the perfect husband and yet, you'll never be perfect. Next they are going to want you to get the perfect job and then have the perfect children. They will always find new things to want and new things to criticize."

Blair's face had hardened as she listened to Chuck degrade her family and her life, "Despite what you think, Bass, my family is very happy with my decisions right now. In fact, it seems that once you were out of the picture the criticism pretty much completely stopped."

"For now," Chuck whispered.

Blair recognized the truth in his words and her shoulder's sagged in defeat, "What do you want from me, Chuck?"

"What do I want? I want you to stop giving a fuck what all those people think!" He spat, gesturing back towards the banquet hall they had come from, "I want you to realize that you can't make everyone happy and I want you to listen to yourself and do what you fucking want for once! Because I know, I know that if you stopped giving a fuck about everyone else and just thought about what you wanted that you would be with me. I know you love me, Blair, and I'm not going to stop fighting until you finally let yourself give in to your true desires."

"Well it's a little too late for that don't you think?" Blair asked snidely, "I love Trip. My 'true desire' is to marry him, not matter what kind of trouble you try to stir up. You're too late."

Chuck's smirk returned, "It's never too late, B. We're inevitable. It doesn't matter if you marry someone else, I won't stop until you are mine again. Even if I have to wait until every single person who disapproves of us is dead in the ground, I'm never going to give up, not as long as I know you still love me."

"Well I don't, so you can save yourself the trouble and just stop now. I already told you once; you're not good enough for me. No matter how much time passes that is never going to change."

Chuck's face fell and his anger returned, "You forget, Waldorf, that I know you. You can lie to yourself, but you can't lie to me. Enjoy your party. I'm sure we will be seeing each other again soon."

Chuck turned and stormed out of the lobby and into his waiting limo as Blair, Serena and Nate watched him go. After a few whispered words with Serena, Nate jogged out of the lobby to catch up with Chuck.

Once he was gone, Serena turned to Blair and sighed, "I'm sorry, B. I didn't know he was going to cause such a scene."

But Blair waved off her apology, "Can you believe that Basstard? Coming here and causing a scene like that?"

"Actually I can."

Blair's looked at her in shock, "What?"

"Blair you know you are my best friend and that I'll always support you," Serena explained, "but I'm Team Chuck on this one."

"You can't be serious." Blair scoffed.

Serena looked away for a moment before she looked at the brunette imploringly, "Look, Blair, can you just do something for me, as my best friend?"

"What is it?" She asked warily.

"I want you to go home tonight and think about what you're doing before we go to meet the wedding planner on Tuesday."

Blair's jaw dropped, "Serena, don't tell me you are going to back out on me now because of Chuck."

Serena sighed and shook her head, "I told you, B, you are my best friend and I will support you in anything you do as long as it is what you want. So, please, for me, go home tonight and think about if this, if a life with Trip, is really what you want. Don't think about what your grandparents, or your parents, or Trip, or Chuck, or even what I want. Just think about what you really and truly want, without the opinions of everyone else."

"Serena," Blair said softly as she looked down, "I can't just-"

Serena quieted her with a raised hand "If it is Trip then I'll be there for you every step of the way. I'll help you plan the biggest, grandest wedding the Upper Eastside has ever seen and I'll stand up front on your wedding day and smile as you say your vows." She flashed best friend a smile before she continued, "But if you can't look me in the eye and tell me that you love Trip with your whole entire heart, then you better start looking for a new maid of honor because I won't participate in something that I think would be a mistake." Serena paused and squeezed Blair's arm reassuringly before she stepped back and looked over her shoulder at the waiting limo, "And as your maid of honor I should probably stay until the end the party, but I'm going to go with Chuck, if you don't mind. He shouldn't be alone right now. Despite his act of bravado, he's taking this whole engagement pretty hard."

Blair nodded with tears in her eyes, "It's okay. I understand."

Serena smiled at her, "Don't worry, I know you will make the right decision for you."

The two girls hugged and Serena walked out, leaving Blair standing there by herself. She took a deep breath and wiped the tears from her eyes. She had a party to get back to. She could think about what Serena had said after it was over.

…

A/N: Meh, this kind of changed from how I originally had planned it, but I couldn't remember how I had originally imagined it. Oh well. The next chapter should be the last one, but it depends how long it gets.

Please review and let me know what you think!