Chapter 4: Jealous Exs of the Upper East Side

"Well me and Ryan broke up!" Serena yelled as she stormed into Blair's room.

"Am I supposed to be surprised?" Blair asked looking up from her book.

"You could ask me what happened. Pretend you gave a crap about someone else's relationship issues beside your own." Serena demanded.

"Fine, what happened?" Blair sighed, placing her bookmark in between the pages.

"He got all mad at me, he said I was jealous of Bree and hung up on Nate. As if." She huffed.

"Both of those things are true, so he is more tuned into reality than I thought."

"I'm not jealous and I don't think of Nate as anything more than a friend." Serena lied

"Serena, they are all you've talked about this entire week. Nate was your most stable and serious relationship, its understandable that seeing him with another girl would bug you."

"It doesn't bug me, and who are you to talk. You can't even be in the same room with Chuck without fighting."

"Yes, fighting because we don't get along."

"Fighting is like foreplay for you two. I can see you guys eye-banging every time you look at each other."

"That's ridiculous. How did this turn into a discussion about me and Chuck?"

"Everything does!" Serena yelled exhausted. "You guys are still connected and it's the elephant in the room where ever you go. And all anyone ever talks about now is Vanessa's wedding plans and you and Chuck."

"That's not my fault. You turned this on me, we were talking about you before you dragged me and Chuck into the conversation!"

"Why are you yelling at me? I just got my heart broken."

"Oh please, he did not break your heart."

"Yes he did."

"Ok, what was his middle name?" Serena starred at Blair as she drew a blank.

"Edward or Bradley…maybe."

"Exactly. You guys were a fling in Bali and that's great. He was fun and you love fun, but he was just a fling. You guys lasted a week in the real world, which honestly is a week longer than I thought you guys would."

"Ryan was perfect, I really thought we connected." Blair stifled a laugh.

"Serena, Ryan was a nobody yoga instructor. You are one of New York's most popular socialites. You two made no sense. It was inevitable that you and Ryan would split. Now you can focus on finding someone more suited to our lifestyle to be with."

"Like Nate."

"No, that's not what I said at all. Nate is with Bree."

"But there not right for each other."

"Serena, as someone whose relationship is currently being under-minded by an ex, I can assure you its not pleasant. Leave him alone. If he breaks up with Bree then you can make your move, but until then be patient."

"I hate being patient."

"Leave them alone Serena."

"Fine," the blonde said holding up her hands in surrender. "But I'm not waiting forever." Blair frowned at Serena disapprovingly. Serena had always gotten whatever she wanted and who ever she wanted whenever she decided she wanted them. Though she was a very sweet girl, she also had a rather spoiled streak, and had never responded to the word 'no' very well, the few times it was ever said to her.

Chuck starred at the Society Section of the New York Times. A picture of Dan and Vanessa graced the page, their happy faces smiling gleefully above the announcement of their engagement. It was entirely not Vanessa and Dan, it was however entirely Lilly. He could practically see her reflection in their eyes as they starred at the camera. She'd forced them into it, insisting it was how an engagement was handled on the Upper East Side. Dan insisted that since they no longer lived on the Upper East Side they shouldn't have to do it. Needless to say the argument did not work.

Chuck closed the paper and looked around the cigar lounge, it was unusually empty, but that was for the best. He didn't need other ears around as he plotted with Carter. Blair had been gone from the city a while, but she had a way of getting people to do anything he wanted. This included having some sadly hopeful Columbian undergrad spy on him as he devised a plan. He looked up when he heard the door to the lounge open. Carter strolled in, his hair was tussled untidily and the sleeves of his shirt were rolled up to his elbows. He sat down, his usual lop-sided grin in place, as Chuck slid Carter his preordered bourbon.

"It was nice of you to show up eventually I guess." Chuck stated taking a puff of his cigar.

"You know I've never been very good at that whole showing up to places on time thing."

"Very true." Chuck noted as he moved the paper off to the side.

"If I didn't have a job secured for me at my father's company I would have been fired the first week."

"I'm so glad Nathaniel grew out of resenting all the privileges his name brought him. It was so tiresome." Chuck reminisced, thinking back on his formerly broody best friend, always forsaking his wealth and power.

"I never understood it, I mean we're only treated better because we are. If he really hated the privilege so much he would have runoff to one of those trendy, hipster Brooklyn bookstores, not sailing every other weekend in Martha's Vineyard and yachting in the Hamptons over the summer."

"He does love boats."

"No, he loves the way girls swoon over him when they see him on a boat." Carter corrected, "And why shouldn't he?"

"I'm glad you're back from California. Life wasn't the same with out you." Chuck said enjoying the banter he and Carter hadn't had much of since he departed for the West Coast.

"So should we just get down to it, this is our old plotting spot if I remember correctly from senior year."

"It is, we planned the demise of that guy from Trinity that hit on Jenny, and took down my uncle when you visited last year."

"So, tell me who are we going to destroy? Marcus? Blair?"

"Both."

"I see, do you have a plan already or do you want to brainstorm?"

"I have an idea of how I plan to ruin their little relationship."

"Do tell."

"I'm going to seduce Blair, for starters."

"I think that might be more of a challenge then you think. She didn't seem to want anything to do with you last week at Dan's."

"Are you doubting me Carter?" Chuck asked incredulously.

"Never."

"Good. Blair's really not as complicated as she wants people to think, she's always been the sentimental type. I think a little reminiscing on the happier moments of our relationship will put her right where I want her. A little PG-13 action and she'll be itching for an excuse to dump Marcus. And when she find's out about his affair, she'll have to leave him. Then she'll run right into my arms…and my bed."

"Clever. I didn't think Marcus was the cheating type, when did it start?"

"It hasn't…yet. A minor detail."

"So you're going to set him up?"

"In a way, all I really need is a picture of him in a compromising position to send to Gossip Girl. Blair hates two things more than anything: lying and public humiliation, for herself that is. She'll have him sprinting to the airport to get on the first plane back to London."

"Ha, well I see you haven't lost your touch."

"I think it will be my most rewarding scheme."

"You do realize you'll be responsible for her humiliation. She'll be the laughing stock of the Upper East Side."

"Only until the next scandal breaks, which will probably be the next day."

"But she'll still be hurt, I'm all for mental warfare, but you're making the girl you love into the enemy."

"Not the enemy, that's Marcus. Blair is just collateral damage. She'll bounce back, but while she's down if I were to be the shoulder she leans on so be it. Like taking advantage of a girl is the worst thing I've ever done."

"I have one question," Chuck nodded for Carter to continue. "Do you want Blair back, or do you just want her to be as miserable as you are?"

"I haven't decided yet."

"Well you might want to, because as if I recall correctly, Blair's not very forgiving."

"Well neither am I."

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