A/N: A few notes about the story. The Kiss on the Lips party never happened for Jenny and Chuck. Jenny never wanted to follow Blair, so she isn't really well know around school. Nate and Serena did happen and Blair knows but she has forgiven him. Blair and chuck never happened. Blair's masked ball never happened so Nate and Jenny never kissed. Nate doesn't know who Jenny is.

Nate Archibald was screwed. That's all there was to it. He was so sick of his girlfriend that it was ridiculous. Now here she was going on and on about her latest "event" that she was planning and he couldn't have cared less. All he could think about was how his parents were practically planning the engagement party when he wanted nothing more than to dump her.

"Hello!?! Are you even listening to me Nate? I'm trying to discuss something important with you."

He looked at the angry brunette in front of him. Sure, she was beautiful but that's about all she had. Nate was so tired of his parent's world where all that mattered was money, looks, and being in control of other people. And Blair was all about appearances. And there was nothing she loved more than proving just how much control she had over everyone. The queen B and everyone should know it. Nate wanted something, no, someone real. Someone who wasn't afraid to do something stupid and embarrass themselves if they knew it would make him laugh. Who would drop everything and be there for him in a second. The only person to ever be like that for him was Chuck. Chuck may be a bit of an ass, but he was Nate's best friend.

Nate was once again brought back to reality by Blair's protests that he wasn't listening to her.

"Sorry. Just have a lot on my mind right now. Tell me about this fantastic party and I'll listen this time."

"Well, it's going to be the party of the year. I mean, it's a Blair Waldorf party. Who could beat it. Anyway. I'm going to hold a Halloween Masque." She paused and Nate knew it was time to fawn over her and her idea.

"That's a great idea Blair. Everyone will love it. Are you going to have a theme?"

Blair beamed at him and he knew that he'd flattered her appropriately. "Yes. Everyone has to come as a fictional character. So no angels or devils or anything boring like that. It must be an actual character, not a general thing. And that's not even the best part! I'm going to get party tiaras made and I'm going to put the mane of every boy invited on the inside of a tiara. Each boy will be sent his tiara before the masque and each tiara will be unique, designed to fit the boy's personality. He'll bring it with him and during the night if he finds a girl he likes then he can give her his tiara. But he has to put it on her so she doesn't see his name. I'll give the jeweler a list of names and a personality description for each boy, so he can make the tiaras and only he will know what each one looks like, so it will be a surprise to even me. Then at the end of the night the boys and girls will go into opposite rooms and the "princesses" will look at their tiaras to find out the identities of their "princes". They then have the option of finding their prince or leaving."

Nate wanted to roll his eyes at the last part. Only Blair would find a guy she really liked and accept his tiara but then bail if she found out his name wasn't up to her standards.

"That actually sounds like fun Blair. And with everyone in masks it will only make it that much more interesting."

"Exactly. And I will not be informing you of my costume choice ahead of time. You'll just have to figure it out on your own."

Nate just let out a sigh as she waltzed out of the restaurant where they had met for lunch without a backward glance or even a good-bye. He paid for the meal and decided that he needed to talk to Chuck. That would definitely cheer him up. He knew that Chuck hadn't been at school this morning and decided that there was no way in hell that he would be attending afternoon classes. He wasn't all that far from The Palace Hotel where Chuck had his suite, so he decided to walk instead of waiting for his car. It would give him time to think.

After he knocked on Chuck's door, he immediately heard a crash, like someone falling off a couch, followed by an angry voice cursing him for knocking on the door.

"Open the door Chuck!"

There was the muffled sound of someone staggering to his feet from the floor and muted footsteps before the door was thrown open.

"Nathaniel!" Chuck yelled. He was standing in the doorway in a purple velvet housecoat and Nate was pretty sure nothing else. It was obvious from the smell that he had been drinking for at least two hours but you would never know it from Chuck's demeanor. He was barely even feeling a buzz. This was a good thing because Nate needed advice and thought the direct approach might be best for getting it. He didn't want Chuck drunk for the conversation they were about to have.

"I want to break up."

Chuck just arched an eyebrow.

"Why Nathaniel? Don't you love me anymore? I'm Chuck Bass."

"Not you Chuck. Blair."

"Well that makes more sense. Congratulations. Come in, this calls for a celebratory drink." Nate just shook his head and laughed, feeling better already. Chuck poured them both a generous glass of scotch and went to sit down in the chair opposite the couch Nate was on. Halfway there, he thought better of it and turned around. He grabbed the rest of the bottle of scotch and an unopened bottle of tequila for good measure. Setting them down on the coffee table he took his chair, ready to play his role of wise man to Nate's blundering idiot. He always enjoyed his role.

"So tell me Nathaniel, why do you want to end things with the-" he broke off, looking for the appropriate word "-lovely" he said in a slightly mocking tone "Blair Waldorf?" Just like the rest of them, Chuck had known Blair their whole lives, and while he found her beautiful and reveled in her vindictiveness, he hated how she treated his best friend. And as he saw it as his job to protect Nate, he didn't have a good view of her and was all for Nate leaving her.

Nate just shook his head, knowing about Chuck's feelings for her. "All she thinks of is herself. We were at lunch today and she was going on about some party that she's planning and she got pissed that I wasn't paying attention. I told her that I had a lot on my mind and she just went back to talking about her party. Didn't even ask if I wanted to talk about it." He reached over, grabbed the bottle of scotch off the table and refilled his glass. Chuck just smiled. It was easier to get Nate to open up when he was drinking.

"All she cares about is money and appearances and social status. She doesn't even really care about Serena, who's supposedly her best friend."

Chuck broke in here. "Nathaniel, I care about money, appearances, social status and power. They're important things to me."

"I know that," Nate argued. "But that's not all you care about. No," he stopped Chuck when he tried to interrupt. "You care about people more than those things. You care about Bart and Lily. You worry about Eric. You love Serena no matter how much you deny it and try to hide it." Chuck opened his mouth, undoubtedly to make some perverted comment, but Nate ignored him. "The whole thing with Georgina, you were ready to do whatever it took to get Serena out of whatever trouble she was in before you even knew the whole story."

This time Chuck did interrupt. "So? What are you getting at Nathaniel? I would do the same for you."

"Exactly!" Nate said, looking smug. Chuck decided he really didn't like the look on anyone's face but him own. "You and I are brothers Chuck, and you see her as a little sister. You're so protective of her and you don't even see realize it."

Chuck was uncomfortable with where this was going so he changed the subject. "We're off topic here Nathaniel. You're supposed to be telling me why you want to drop the Ice Queen."

Nate gave him a look that said 'I know what you're doing' but he let it drop. "I want something real Chuck. Someone I can't wait to see and talk to everyday. When I walk into a room, I want her to be the first person I see, immediately, no matter where she is. Someone I can sit with for hours and talk about absolutely nothing without getting bored. The first person I think of in the morning and the last person before I fall asleep. Someone I would rather die than hurt." Then because the two of them didn't do serious well he added, "Do you want to know who that person is for me now? It's you. And frankly that makes me uncomfortable."

Chuck smirked at the last part before just staring at him. "You Nathaniel are horribly romantic and cliché."

"Yes Charles, I know." He looked at Chuck for a minute. "But don't you want . . ." he struggled to find the right words. "-just more."

And because it was only the two of them; Chuck and Nate like it always had been, best friends, brothers; Chuck let his down his guard enough for Nate to see the longing in his eyes and said "Of course Nate." Just like that the wall was back up and with a true Chuck smirk he said "But as you pointed out before, I haven't found anyone besides you and Serena worth of Chuck Bass."

Nate couldn't help the laugh that came out before he became serious again.

"How am I supposed to do this Chuck? My parents are already planning the engagement party."

Chuck was quiet for a moment, thinking. "You said she was planning a party, right? Well the day of the party just tell her that you aren't going to be taking her and she'll get the message that you're through. And when she shows up alone everyone else will too." He paused at Nate's frown.

"That might have worked if she wasn't planning a Halloween Masque. No one is supposed to bring a date. She's got this whole thing worked out about finding someone amongst the masked people, not knowing who they are. And she also expects me to find her without telling me what her costume is." He got a confused look on his face as Chuck smiled.

"You cannot withhold important information like this from me when I'm scheming Nathaniel." Nate shot him a look that said 'What are you talking about?' as he opened the bottle of tequila and downed a double shot before pouring another. "Everyone is going to be in masks at this party right?" Nate nodded, still confused. "And Miss Priss isn't expecting you two to show up together, right?" Another nod. "So we just have to find you a great costume so she won't know it's you and bother you all night and then you're free to find your mystery dream girl."

Nate didn't say anything. Just poured two double shots of tequila, handed one to Chuck, and toasted his best friend and "the plan" before both boys knocked it back in a synchronized more perfected from years of practice.

*****************

Jenny Humphrey was sitting on a bench in the Constance Billiard commons during lunch period completely absorbed in the book in front of her. Her hand flew across the page and she didn't notice anything around her. Anika (ah-knee-ka), Jenny's best friend, had sat down next to her almost five minutes ago and was talking to her and Jenny didn't even notice.

"Guinevere Humphrey!"

Jenny jumped and almost ruined the page she was working on by running her charcoal pencil across it, but she managed to jerk her hand away just in time.

"Nik! Way to announce you're presence subtly. I thought we were working on that." She shot her best friend a sarcastic look. "And what's with the whole first name Anika?"

"Well Jen, if you had been paying the slightest bit of attention, you would know that I've been sitting here telling you about the most important gossip of the YEAR for the past five minutes."

They sat in silence for thirty seconds before Jenny snapped.

"Are you going to tell me this all important gossip or not?"
Nik sent Jenny a sly smile before stating plainly and with no hint of embarrassment "I want Chuck Bass."

"Eww! Why?" was the immediate and instinctive response.

"Because he's so pretty." was promptly shot back. She got a far off look and a goofy grin on her face before she brought herself back. "But that's not the point. So I was walking down the hall minding my own business" she saw the disbelieving look Jenny shot her. "Ok I was walking near them and overheard" another skeptical look. "Fine, so I was eavesdropping, but Chuck wasn't in school this morning and I wanted to know why. Sue me. Anyway I overheard her majesty telling Serena about some party she's planning. Apparently, Serena was the first person she was telling about it, and now I'm the second person to know all about it."

Jenny had to laugh at Nik's enthusiasm. "Well are you going to make me the third, or leave me to wallow in y ignorance alone?"

"There's no need to be dramatic Jenny." Nik ignored the incredulous look Jenny shot her. "And of course I'm going to tell you. You're my designer."

Jenny let out a snort. "Somehow I don't think we'll be invited."

"Of course we will. You're brother's dating Serena van der Woodsen."

"Okay. What do you know that I don't?"

"Well this could take days. Where to start? A golf ball has 318 dimples. An ostrich's eye is bigger than its brain. This may be your change to talk to a gorgeous blue-eyes junior. Everyone's left foot is slightly bigger than their right. Two wrongs don't make a right but three lefts do. The-"

"Anika!" Jenny yelled, trying to keep the amusement out of her voice. "Focus!"

"Oh, you mean what do I know that you don't about us being invited to the party. Jeez Jenny you have to be more specific." Nik teased. Jenny looked unimpressed. "Well Serena was telling her royal highness that she didn't know if she would be there because she didn't think that Dan would go for it, given his aversion to all things popularity related. Anyway, Queen B said that Dan is so smitten with Serena that he would come to the party in a dress and heels if he got to be with her. Then she said, and I quote, 'To persuade him further, I'll even invite Little J and the weird friend.' So as long as your brother goes, we're in. Why does she like you so much anyway?"

Jenny laughed. "She doesn't 'like' me; she's just not threatened by me. I occasionally do things that benefit her and I have no designs t dethrone her. Plus, as Serena's boyfriend's little sister she makes and effort to be civil. She doesn't 'like' anyone."

Anika half shrugged half nodded as if to say 'True'.

"Okay" Jenny conceded. "We may be conditionally invited, but we'll never get Dan to-"

Anika had to bite her lip to keep from laughing as Jenny turned bright red, having just realized what she had said earlier.

"What do you mean 'gorgeous blue-eyed junior'? I don't know any gorgeous blue-eyed juniors. And even if I did, the gorgeous wonderful perfect brilliant-" Nik cleared her throat loudly to get Jenny back on track "-blue-eyed junior would already have a date. And he wouldn't blow her off for a midget freshman."

"You're not a midget Jenny. You're only a little short; you just happen to not wear heels to school so that makes you shorter than most girls here. And for argument numero dos: the gorgeous wonderful perfect brilliant-" she let out a small shriek as Jenny tried to push her off the bench for mocking her "-blue-eyed junior that you 'don't know' isn't going to have a date. No one is. It's 'against the rules'."

"What kind of party is this? Blair would never go in public without a date."

"Break out the tights Tink. We're going to a Halloween Masque."

Jenny squealed. The two of them had been wanting to go to a costume party for years, but they weren't considered the 'in thing' to do for parties. Not they would finally get their chance. They could talk to the most popular people in school without being 'Little Jenny Humphrey and her weird friend'. She brought herself down before she got too excited.

"Does the party have a theme?" Nik didn't say anything, just nodded. "Knowing Blair it's probably something like Arabian Nights. She'll make everyone else come as belly dancers and she'll show up in a one of a kind dress as the Queen of the Arabians." Jenny pulled a disgusted face. "I'd rather not go than go as a belly dancer."

"So it's a good think the theme isn't Arabian Nights then isn't it Jen." She didn't say anything else and Jenny nearly tackled her, trying to get her to tell the theme. When she started to reach for Nick's stomach to tickle her, she finally relented. "The theme of the Halloween Masque is simply "Fictional Characters". There will be no generic angels, devils, princesses, pirates allowed. You must be recognizable as an actual character or be turned away at the door.

By this time Jenny was practically vibrating with excitement. She and Nik had long a go picked out what they would go as if there was ever a costume party. Nik, with her skinny dancers body, long red curls, and complete un-self-consciousness about her body, would go as Ariel from The Little Mermaid. Jenny, with her slightly below average height, natural bleach blonde hair, and gorgeous hourglass figure, would be Tinkerbell, the playful pixie of Neverland.

"You still have the costume sketches, don't you?" Nik was just as excited as her, bouncing up and down on the bench.

"Oh course." Jenny chewed on her bottom lip for a minute. "We might have to make some minor adjustments though. We designed them in the sixth grade."

"Probably." Nik said grudgingly. "I may not have gotten much more curve in the last three years, but I've certainly gotten taller."

"And I've gotten more curve but I'm pretty sure I haven't even grown an inch since I was eleven. I'm doomed to be 5'4 ½" forever." Both girls were silent for a minute, each having their own pity party. Jenny was the first one to snap out of it. "Oh well. Meet after school to go over the sketches?"

"Is Rufus cooking?"

"Waffles."

"I'm in."

The bell rang to signal the end of lunch and the girls gathered their things to journey to their respective classes. Just before they parted, an important detail caught Jenny's attention.

"Nik, what day is she having the party? Oh my god. Knowing Blair, she'll want to have it early so it's the first Halloween party that anyone throws. I won't have time to finish the costumes and then we WILL have to go as belly dancers and-" she was cut off by a hand over her mouth.

"Relax Jenny. It's on Halloween. Something about custom tiaras and art takes time. I had stopped listening by then because they hadn't mentioned Chuck."

Jenny had to laugh. "Hey Nik, you remember what you told me about the ostrich?"

"Yeah."

"You guys totally have that in common."

Jenny dodged the slap and took off for her next class.