One warning though, I have seen a lot of spoilers and while I'm not working off of those some of them may appear in my story because they fit too perfectly not to. But from here on out I am pretty sure my story differs enough that I am on my own.

Disclaimer: I do not own Gossip Girl or its characters

Rated: T mostly for language. This one isn't really M but it is a pretty high T lol.

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Dan watched from his and Serena's usual table in the courtyard as Blair and Jenny walked out of the library that separated the two schools with their arms linked. He didn't understand. He thought that Jenny was over trying to be friends with Blair Waldorf. Blair was a bitch and when Jenny was around her she became a person that Dan didn't like very much. Dan was so deep in thought that he didn't even notice Serena come up, until she wrapped her arms around him.

"What's on your mind Dan?" Serena asked as she stepped around in front of him.

How did he get so lucky, Dan thought. Serena was easily the most beautiful girl he had ever seen yet she picked him, twice. He didn't want to upset her by talking badly about Blair though. Blair was her best friend and she was protective of her to say the least. "Don't get mad okay."

Serena looked at Dan, something was bothering him, so she nodded to signify her compliance and Dan gestured with his head towards the curb.

When Serena turned around, she saw Blair and Jenny getting into a cab. Oh, that's what was bothering Dan. She turned back around to face Dan. She couldn't very well tell Dan how Blair and Jenny had gotten to be friends without telling Dan about Jenny and Nate in the Hamptons and she didn't want to do that to Jenny. "Don't worry about those two Dan." Serena said, trying to be reassuring.

"How can I not worry after what happened last time?" Dan said remembering the way Jenny had acted last spring. He hadn't liked his little sister very much back then and he didn't want his sister acting that way. She was better than that. "That girl, the girl Jenny turned into wasn't a good person and I don't want that happening again. Not to mention the fact that Blair doesn't care one bit about Jenny, she just wants another little minion to order around."

"Dan, I'll admit that Jenny went a little overboard last year but you have to trust that she knows what she's doing. And about Blair, Blair's different now. She isn't the same person she was a year ago either and I really think that she considers Jenny a friend." By the incredulous look on Dan's face, she could tell that he didn't believe for a second that Blair had changed. "Dan I swear, I've seen it myself, Blair is more mature and I have seen her with Jenny. She doesn't treat her like she did last year, she doesn't treat her like she does those other 'friends' of hers either, Blair treats Jenny like a friend, like she treats me."

"I still don't like it." Dan said with a grumpy but subdued expression.

"You don't have to like it Dan, you just have to deal with it." Serena said matter-of-factly. "Jenny's growing up, she's almost sixteen and you can't keep interfering in her life. I know you love her but at some point, you have to let her grow up on her own."

"I know" Dan said. "I just want what's best for her and I want to see her grow up to be a person that I can respect, you know."

"Yeah, I know. But that goes back to you having to trust her to make good decisions and as much as I know you aren't going to like this, you have to trust Blair." Serena reached over and laced her fingers through Dan's hand before tugging him to his feet. "Come on, lets go to the café, I want coffee."

Dan smiled as Serena drug him to a cab. As much as he hated to admit it Serena was right. He had to let Jenny make her own choices and just hope that they were the right ones.

Tick tock Upper East Siders, the clock has struck four and you down to only twelve a week. At eight tonight when you are down to only four it will be only minus one every hour but by then it's not as much of a prize anyway is it?

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Chuck took a long hit before sitting down on the bench next to Nate. Nate was glaring a little, but the pot had mellowed him out a lot from before. Now the glare was more appraising. What had driven Chuck towards Blair? Was it what was driving him towards Jenny? That he couldn't have her, or was it something else, did he always have feelings for Blair? What was it about her that caused him to want her so badly that he would risk their friendship. Chuck had told him right before they left the Hamptons that he and Blair were together again and that they had to keep it a secret for reasons that they couldn't say. He had just shrugged and gone along with it. He hadn't even asked what had brought them back together, what kind of friend was he? He and Chuck had been friends for as long as either could remember but he realized now that he didn't really know that much about Chuck, yet he felt like Chuck knew everything about him. How had that happened? When did he stop knowing what was going on with his best friend? Had he ever known?

Nate looked like he was contemplating something serious. His expression wasn't blank and his eyes were alert even though he had been smoking. Chuck couldn't help but think that this didn't happen all that often with Nate. Nate was a little bit of an open book. Always doing or saying the first thing that popped into his head. He always shared what was going on in his life with Chuck and it was Chuck's job to sort through the mess and the drama and find the proper solution for Nate. It had been that way for as long as he could remember but right now, right now Chuck had no clue what was going through Nate's head. Since when did Nate sleep with random girls, especially ones that he at one time called friends like Jenny. Did Nate not feel like he could confide in him anymore? Had Nate tried and Chuck simply been too wrapped up in Blair? Their friendship had been so strong but right now he didn't feel as though he knew the person sitting next to him.

"When did we switch roles?" Chuck said at the same time Nate said "What drew you to Blair?"

Both boys laughed, they would start talking at the same time. "You first." Chuck said.

"Okay." Nate smiled. "What I was trying to ask, was what drew you to Blair, like what made you want to be with her more than once? You had never wanted that before, so why her? And don't worry this isn't about me wanting Blair back or anything, I was just wondering what changed you."

Chuck smiled a genuine smile as he said, "I honestly don't know. I can't even tell you how long I had felt that way about Blair. I might have been in love with her from the start, I mean as far back as when we were children she was the only girl that I was ever curious about. The other girls were all so available and there was absolutely no mystery to any of them. I mean, she was the only girl I ever respected enough not to try something with, not to mention the only girl who schemes as much as I do. But for oh I don't know ninety percent of our lives, she was your girlfriend. And I really don't know that it was one thing, more one hundred things that made me want her."

Nate had never heard Chuck be quite so forthcoming with him, it was different, and Nate kind of liked knowing how Chuck thought. "Was one of those things, the fact that you weren't suppose to want her?" Nate questioned.

Chuck couldn't help but laugh. "That I couldn't have her, or maybe just that I shouldn't have her was the whole reason I chased her initially. Or at least that's what I told myself. You know me Nathaniel, it was always about the chase for me before Blair. But then with Blair, after I had had her, I still wanted her. That was so new to me. And maybe that too was partially because I shouldn't want her, she was your girl. When you wanted her back, I had this awful gut wrenching feeling that I would die if I lost her, and honestly I thought I was going to. When she went back to you it almost killed me. I was so angry at her for getting back with you that I said awful things to her but I don't think that I realized at that point that what I felt for Blair was love. Eventually, I did though, It was like I was drowning in all things Blair and I wasn't even with her. So I had to get her back, which I did. Then I got scared and pushed her as far away as I could and I think you know the rest." He had forgotten he was talking to Nate, but once he had started talking about how he felt about Blair, he just couldn't stop. When he looked over at Nate, his mouth was open as if he was in shock.

How could that have all happened without him knowing. Sure he had been preoccupied with other things, and at first Chuck hadn't talked to him about it for obvious reasons, then he had been so mad at Chuck that he wouldn't have listened but after that they had been okay, so why had they never talked about this? There weren't words for what he was thinking, all he could say was. "I didn't know."

"I know man, and I never blamed you for not knowing. I told you any of it before." Chuck was surprised but it felt good having someone to talk to. "So, what's on your mind Nathaniel, what's going on with you? I had said that it felt like we had switched roles recently me being the committed one, you going from girl to girl, what happened?"

Nate leaned his head back and sighed. "I thought that I wanted Vanessa and I was going to tell her until Serena told me that she and Dan were an actual couple. Serena wanted us to pretend to be together so that she didn't have to be alone so I agreed. Over the next month, I thought that I had fallen back in love with her, Serena that is, so I told her. But she told me exactly what she told me a year before. She didn't feel that way about me, she wanted Dan. So I made a decision to be more like you." Nate looked over at Chuck who couldn't help but interrupt.

"More like me?" Chuck had almost choked on the hit he was taking.

"Yes Chuck, I wanted to be the old you. I wanted to be able to not care about girls, to just sleep with whoever I want and not get involved. I started that experiment with some random girl at the last party in the Hamptons. I was drunk out of my mind and I had told myself that I didn't care who the girl was. Turns out it was Jenny." Nate let his head fall into his hands.

"I know, Blair told me." Chuck said quietly.

"Wait, Blair knows?" Nate said turning his head to face Chuck, who simply nodded. "That explains some of the cold looks I've gotten from her lately." Nate then continued with his story. "So then I started sleeping with every girl who would take me and I haven't been turned down yet. It got boring so quickly. Then I just wanted a challenge and Jenny well I knew that she would be a challenge, so I went for it with her. She didn't refuse until she lost control and then I just didn't want to stop. Damn it man, I just feel, I don't even know how to say it, I feel . . ."

"Lost" Chuck said filling in the blank. "You feel lost."

Nate studied his friend. "Yeah, that's it exactly, how did you . . .?"

"Know." Again Chuck filled in the blank. "I know because I've been there. Hell, I lived there for seventeen years of my life. It took finding Blair, to find myself. And as much as I hate that you are in that place I have to tell you that there's no easy way out of it. I spent my entire adolescence sleeping with every girl I met and I thought that that made me safe. Because I knew who I was, I knew that I was Chuck Bass and even though people despised me, I was okay with that. Then Blair happened and I wasn't okay with that anymore. She made me realize that I had been so wrong about everything that I thought I had been right about. It wasn't okay to just be that guy anymore. Somehow during that time I was even more lost. Lost between loving and hating Blair and loving and hating myself. It's hard, really hard but I'm not lost anymore, so it was all worth it."

Nate groaned, Chuck was getting a little sappy again. "Okay, okay, don't go all chick flick on me over there." Nate said.

Chuck smirked. "So now I have something to ask you" Nate motioned for him to go ahead. "Were you the guy with Penelope?"

Nate's expression told Chuck everything. He and Blair had been right but could he still do this. Could he be the person to throw Nate to the lions when he was clearly so lost. That would only cause him to slip further into this blackness that was starting to consume him. Chuck would know. So Chuck got out his phone and texted Blair.

B

I'm still w/ N. It's bad. He's our guy but I can't rat him out to GG. 2 hard 2 explain in text. Palace bar 6.

C

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Blair read Chuck's text message and felt her heart drop. Of course they couldn't tell on Nate with the whole Non-Judgmental Breakfast Club thing that they had going. What he did they did. She had just kind of been hoping that this had been their way out. After an afternoon shopping with Jenny and commenting on guys that she would look cute with, it just made her want to be able to be out in public with Chuck even more. Right now they were sitting at Fred's Café drinking coffee and eating sandwiches while they gossiped.

Jenny could tell by Blair's expression that the text she had just gotten had upset her. So she sat down her sandwich and tried to talk to her. "Hey, what's wrong?"

Blair tried to shake herself out of the melancholy mood that the text had just put her in. "Nothing that a little retail therapy can't fix." Blair said as she plastered a fake smile on her face.

Jenny wasn't fooled though. "After everything that I've told you over the past week and everything you have done for me, you have to know that you can talk to me. About anything at all. You need someone to be able to talk to B."

Blair couldn't help but give a little smile. Jenny Humphrey of all people was trying to comfort her. Well, she might as well go ahead and tell her. After all Blair had enough dirt on Jenny that she could destroy her all over again. But oddly enough, Blair trusted Jenny, quite possibly more than she even trusted Serena. "Okay." Blair replied before telling Jenny everything. "Well it started back when Nate and I were still together back at the beginning of last year, as you know he slept with Serena and the whole Masquerade thing but there was so much pressure from our parents and other people to be together so we were. Then you told me about the Masquerade ordeal and that night I asked Nate if he was in love with me. He didn't answer and I broke up with him. That was the night that I went to Victrola with Chuck. I had been drinking and Chuck dared me to get up on stage and strip. I did it because that was just the kind of mood I was in and latter that night when Chuck was driving me home in his limo, I lost my virginity." Blair paused to catch her breath.

"Wait, so you were serious about the whole losing it in a limo thing?" Blair nodded. "Wow, I mean that's incredibly romantic." Jenny said with a huge smile.

Blair was surprised. Of all of the words to describe what she and Chuck did in that limo, romantic was never one she would have thought of, but in all actuality it kind of fit. "I assumed that Chuck would treat me like any other girl and ignore me but he didn't. In fact he followed me around and on my birthday he bet that Nate wouldn't show. He was right and we ended up in bed together, again. But he also gave me my amazing Erikson Beamon necklace that night and treated me like a princess. After that we were pretty much always together. I was so happy, so free. Then Nate wanted me back and I didn't know what to do. I didn't want to be attracted to Chuck, I thought that I was suppose to be with Nate, and then Chuck screwed up. He manipulated me and I went running back to Nate. Chuck proceeded to blackmail me with our affair to keep me from being with Nate. I got together with Nate anyway then the whole pregnancy thing happened and Chuck blogged to Gossip Girl. He had wanted me to lose everyone so that I only had him left but then when that happened, he was so pissed at me for ruining his relationship with Nate that he said some awful things and I almost left for Italy. Everything else, I could have dealt with, but that was the one thing that made me just want to give up and leave. Chuck didn't want me anymore."

Jenny felt like she should say something. After all, at least part of that mess was her fault. "I'm sorry about all of that Blair. I mean I didn't know about everything that you were going through back then and I shouldn't have said anything."

"That's all water under the bridge now, don't worry about it." Blair said with a smile. "Serena convinced me to stay and you know the rest of that semester. Chuck and I got rid of Georgina together and then at the wedding he told me that he wanted me back. He was sorry for everything and wanted us to be together for real. I was in love but there was no way I was going to admit that to him. We were going to Tuscany together but Chuck bailed. That was hard, so hard. I didn't think I was going to make it through the summer. Then Serena convinced me to come to the Hamptons, so I came and brought Marcus. I couldn't show up to the Hamptons alone and so I used him to make Chuck jealous. Chuck saw right through it though. He called my bluff and promised me he was going to fight for me. He moved in to the Van der Bass house to be around me and proceeded to woe me all over again. He even wrote me a song about doing Whatever it Takes to get me back. He confessed all of his feelings and told me that he loves me and told me why he was so scared to be with me. It was magical."

"Then why are you and Marcus still together? I mean you're engaged Blair." Jenny questioned.

"Marcus videotaped me and Chuck together. Turns out he knew all along what was going on. As good as Chuck and I are at scheming, Marcus is better. He threatened to show the tape and I said that I didn't care. Chuck and I were committed and I had been planning on ending things with Marcus for good anyway. Then Marcus pulled out a file on Chuck. He's got a case, falsified evidence and everything against Chuck and if I don't go through with the marriage Marcus is going to have Chuck sent to jail."

At this Jenny's mouth had dropped open. She didn't know people actually did this kind of thing in real life. She thought that it was all in the movies.

"Yeah, so I broke Chuck's heart and tried to make him hate me. You were at the party, you say me and Chuck dance and fight. But Serena interfered again and figured things out. She told Chuck and he overheard me and Marcus. He vowed that we would fix this and so we have been trying ever since. We were hoping that we would be able to get the prize Gossip Girl was offering because then we could be together without being afraid that Gossip Girl would tip off Marcus. But there's no way that is going to happen."

Jenny suddenly realized that she knew what Gossip Girl wanted to know. "Yes there is B. It was Nate the guy was Nate, he told me so himself, today in the library." Jenny was excited. Maybe she could help Blair.

"I know. But Nate is still one of my best friends and I can't turn him into Gossip Girl." Blair said frowning.

Jenny realized then, that the text message had been confirming what Blair had probably already suspected, that the guy had been Nate. "I'm so sorry B."

"It's okay Jenny, this mess isn't your fault. I did this myself and now Chuck and I are dealing with the consequences. I need to go, I have to meet Chuck. Can I drop you off somewhere?"

"Yeah actually I kind of need to go by your mom's office, I have some stuff to finish up."

"Sure." Blair said as she stood up, leaving the tip for the waiter.

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"Sorry I'm late." Blair said, sitting down next to Chuck at the bar. It was six fifteen, she was almost never late but there had been some traffic.

Chuck stood up and gave her a hug. "Do you want to head upstairs. I don't want to be seen."

Blair got up and started heading towards the elevator before Chuck had even finished. Once they were both inside she said in a quiet voice. "I wish it wasn't Nate. If it was any other guy I could do it but Nate I can't do it to him."

"I know B," Chuck said lacing his fingers through hers and kissing her hand. "Nate's really lost right now. If this came out, I don't know what it would do to him."

"Don't worry, I get it. It's the whole Non-Judgey Breakfast Club thing. Lets just make do with the time we have. We are going to have to start finding ways to get around Marcus's ultimatum, we don't have time to worry about being seen in public so we will just have to be careful."

By this time they were in Chuck's room. He knew that they had a lot of work to do but tonight he just wanted to be with her and pretend like the rest of the world didn't matter. So he shut the blinds, locked the door, put out the do not disturb sign, and came back to Blair. Where he kissed her and pulled her onto the bed.

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Jenny was looking through her bag for one of her sketches when she saw the camera. Why on earth was it still blinking. OMG it was recording. It had been recording all along. That meant that Nate's confession was caught on tape. She opened the camera and rewound to the point in the library. There was a perfect view from the camera's position on the floor where she had dropped it when Nate scared her. Jenny quickly loaded the file onto her computer. Blair might not be able to turn in Nate, but she sure could and she had concrete evidence. A videotaped confession. Jenny opened her webmail where she sent an email to Gossip Girl.

Gossip Girl,

I want to make a deal. I know who your mystery man is and I have proof but I don't want your prize. I want you word that you wont publish anything about the relationship between Chuck and Blair. I don't care what you post about me and other things related to Blair as long as you don't out her and Chuck's relationship and don't tell who won the competition, just keep it quiet.

Little J

Jenny sat nervously at her computer waiting but she didn't have to wait long. The response was one word.

Deal

So Jenny attached the video (edited to be just the part where Nate admitted his affair, she didn't need Gossip Girl seeing the rest) and sent the email back.

Ladies and Gentlemen we have a winner, who has asked to remain anonymous. I have agreed to the winner's terms and am proud to announce that our mysterious man was none other than our very own N and from the sounds of the clip I received P isn't the only girl he's been messing with. Poor N, you seem a little lost, you've gone from dating the Queen B to screwing social outcasts behind the school. Find your way back to us soon.

xoxo

Gossip Girl

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AN: This one took forever, I hope you all enjoyed. Thank you to those of you who review. It makes me happy :)