A/N: Hi everyone! This is my first Gossip Girl fanfic, it will be playing out the tv show and I have not read the books. Slight AU, everyone attends the same school which is St. Jude's. Hope you all enjoy. Please R&R.

Also a warning! My OC will have mental health issues and OCD. If that is in any way a trigger for you to read, turn away from this. Though she not in any way suicidal, she is being bullied.

~X~

New York drove Leonora insane. The people, the buildings, the noise. Everything added up to one nice, permanent headache. Today that particular headache was in a form of a party that her father had promised that it would be a quick in and out situation. They had been there for over an hour. Leo didn't even know who organised this gathering, but her father had said that it was good to socialize with others that were the same age as her. Looking around the room, she felt as if didn't belong on the upper east side of New York.

But she was, in fact, the daughter to the one and only Tyler Knight. One of the world's wealthiest men alive. He owned the Knight Group, an insurance company that worked globally with other wealthy people and their insurance, from anything like a dog to a house or family members. Because of this, she went wherever he went. And for now that would be the big apple.

"So Nate, started to think about college yet?" A man in the circle that Leo and her father stood in asked. Nate Archibald was a guy in Leo's school. They did not have many classes together since most of Leo's schedule consisted of AP classes.

"Well actually I'm a Dartmouth man" His father stated with confidence. Leo wanted to roll her eyes, as always, the father had the last word about his son's education. Like Nate was just a doll to be presented to the world. 'Look, my son does this, went there and can work with this' and another man would say 'This is my daughter, she does this and is very pretty. She is also prepared to drop everything in her life for your son'.

"Yes, dad's always spoken highly of Dartmouth, but I would like to check out west, maybe USC or USLA" Nate said, his eyes glaring daggers at his father. Yet also seeking approval in some way.

"His mother wouldn't have it, Dartmouth is far away enough for her" And that is final. Leo thought and sipped on her drink.

"What about your daughter Tyler?" The same man turned to her father as if Leo wouldn't be able to open her own mouth to speak.

"Oh I am very proud of her, 4.0 average and I get emails everyday from Ivy League schools trying to take her away from me. But I want her to finish at the normal pace you know, life is no rush" Tyler stated as he drank his whiskey. The other men around him nodded.

"So do you have any particular school in mind?" The man asked Leo who looked like a deer caught by headlights on a freeway.

"Umm.. I have so many to pick from, but Harvard sounds amazing. I also got a letter from the university of Oxford in England, and since my older brothers are in charge of father's company division in London I think it is an option to consider" Leo smiled. She hadn't stammered once, nor fidget with her hands. She even looked him in the eyes, but then looked at her father instead for comfort.

"Just brilliant, you have done good raising her Tyler" Another man stated and clapped her father on the back. The other's joined in on the praise. Nate's father just stood there quietly, looking over at Leo then to his own son.

"Excuse me Captain, Nate can I borrow you?" The one and only Blair Waldorf asked. Smiling like a little angel. With Nate gone, Leo moved out of the group and towards the table with the different foods and desserts. As she placed down her glass, she picked up a small bowl of strawberries and started to eat them one by one. Trying discreetly to move closer to the exit. She would explain to her father later that evening that she felt sick and went home, and that she forgot to text him because of her light-headed state.

"Well look what we have here, the black sheep trying to escape the herd" A voice exclaimed behind her. Leo turned around to face Chuck Bass. Her arch-nemesis.

"Chuck, just please let me go" She stated, he would rat her out in front of her father's friends. Which would then turn into gossip. Leonora Knight dreaded gossip.

"Why is that Leonora? Are you not having fun?" He chuckled in his husky voice, Leo shuddered and turned her head towards her father's direction. He hadn't noticed her yet.

"No, and I want to go home" She said and put her bowl down on a nearby table. She looked Chuck in the eyes as if to say 'I dare you'.

"But you know that I will cause a scene if you go.. and right now we are having so much fun" He threatened. He had bullied Leo since first year of high school when she had spilled her water all over him in the middle of the cafeteria. Everyone had laughed at him. And it wasn't so much spilling the water as it was throwing it at him. Since he touched her without a heads-up.

"Will you ever let it go Chuck? You know that I couldn't help it" Ah, and then it was the fact that Chuck knew about her mental health issues and also the obsessive compulsive disorder. The price you gotta pay for an IQ over 130.

"Who knows, all I know is that toying with you is fun. See you around, Leonora?" He said, then stepped away to go and talk to some of Blair's minions. Leo sighed and hugged herself. She felt like a coward, because all she wanted to do was to get out of the poisonous party.

"Are you alright?" Leo opened her eyes to find Nate standing there. She furrowed her eyebrows. He never talked to her. Or acknowledged her existence for that matter.

"Yeah, I'm.. I'm fine" She said and turned away from him.

"What did Chuck say to you, he can be a real ass you know" Nate stated and looked straight at her. She felt naked, why was he staring?

"He.. He just says stuff sometimes, it's fine really" Leo tried to convince him, but since she wouldn't meet his gaze he knew it was more than what she tried to play it off as.

"I will talk to him-"

"No! Please, don't. Nate, I'm fine. I just really need some air" Leo said and walked out the front door. To hell with Chuck Bass.

Leo didn't know, but Nate looked at her until he couldn't spot her anymore down the hallway. He had just gotten over Serena and he was still together with Blair. But it was something about Leo that made him smile.

~X~

Knight Residence, Upper East Side

Monday

"Ah there she is! My little genius is a junior now" Chris exclaimed. He had been Leo's nanny ever since she was a toddler, and he was a great one too. Chris Andrews had been a high positioned agent at one of New York's best model agencies before he decided that he needed a break from all the glamour and made a fabulous exist to live a 'simple life'. He apparently knew Tyler from a couple of parties back in the day and when an old friend called in to baby sit, just over the weekend, Chris gladly accepted. He then fell in love with little Leo so much that when Tyler said he was looking for a nanny he took the position with pride.

"You are way too excited" Leo sighed and adjusted her skirt. Chris had probably hemmed it without her knowing it, again.

"Stop pulling at it! You look gorgeous honey" Chris said and fixed her tie so that it was straight. Leo had braided her black hair into boxer braids, since it was way to unruly and wild to just keep down. While eating a quick and amazing breakfast, all regards to Chris's wonderful cooking, she did the crossword puzzle in the New York Times. Chris hummed a tune from the radio while going over a fashion magazine, at the same time packing Leo's lunch, just to look up at the clock on the wall and gasp.

"Leo you better get ready to run dear, you will be late for school" Chris sighed and gave her the lunch boxes. Leo almost choked on her orange juice and gathered up her things.

"Bye Chris, I will be home as usual. Love you!" Leo shouted as she sprinted towards the elevator.

"Love you too honey!"

~X~

St. Jude's

"For the first assignment of this semester you will work in a group of two, you will choose a mythology or non-abrahamic religion and do a presentation together in front of the whole class. The things you need to have in your presentation are questions like, what was the effect by the mythology on society of the time? Are there traces of those mythologies still in modern society? Etc. You will have two weeks to complete it and it will have a great effect of your grade" The teacher of AP history wrote every word he said on the board. Leo sat by the the window, but was nose deep in writing down notes to remember for later.

The teacher of the class was very strict and old fashioned. He believed in old fashioned good work and gave every half-assed assignment an automatic F after reading the first paragraph.

"And the pairs are.. Adam B and Greg, Juliette and Lorelei G.. Klara and Chuck" The teacher wrote to lists next to the assignment. Leo did not care about this part. She just hoped that whoever was partners up with her would not let her do all of her work alone.

"Leonora and Nathaniel" Leo stopped writing and looked up, you've gotta be kidding with me! Leo thought and looked around the classroom, halfway through she met Nate's eyes. What does the universe have planned. That boy seemed to show up everywhere since that stupid party.

~X~

Lunch

"Leonora! Hey!" She looked up from her greek mythology book and spotted Blair Waldorf sitting a couple of steps to her right. First she looked around to see who she really meant, then she realised she had called her out by name.

"Hello?" Leo said, barely audible.

"Here, take this" Blair said and gave her a golden letter. Raising her eyebrow she opened it and read the invitation.

"Why would you…"

"Just take it okay? It is on Saturday"

"But-" Leo would've argued against it. Then spotted Serena beside Blair. They had been fighting passive aggressively and were now having a glaring contest.

"Fine.. thank you for the invite" Leo sighed and stood up from the steps. She really needed to get away from the drama. Still feeling eyes on her back, she picked up the pace. When she finally reached the school grounds again she opened the letter and read the whole thing. It all seemed off, she had never been invited to any party before. She didn't even care about these parties anyway. She turned the invite and saw none other than Chuck Bass's neat handwriting.

Hope you save me a dance princess

XO you know who

"Why doesn't he just leave me alone" Leo muttered and threw the letter into her leather bag.

~X~

Central Park

Nate and Chuck POV

Walking with Chuck made Nathaniel relax and tense up at the same time. How could that be? Well he felt like he could tell Chuck anything, but he had to be careful about his words of choice.

"This is some good stuff" Chuck commented while blowing smoke out of his mouth.

"Yeah I'm gonna need it, Blair's mom is at the countryhouse" Nate exclaimed, but didn't seem happy about that at all.

"Yeah, well then maybe I should swipe some of my dad's viagra.. or my mom's paxil?" Chuck looked at his best friend.

"Nathaniel you are about to have sex with your girlfriend, you act like you are headed to your execution" He added, now frowning to get Nate to fuss up.

"Nah man I'm good" Nate just wanted him to drop the matter, but he was damn persistent.

"Talk to Chuck buddy, you and Blair have been dating since forever and all of the sudden there's a problem?"

"There's no problem, it is just... do you ever feel like our whole lives have been planned out for us? Like we are just gonna end up like our parents" Nate murmured, feeling a slight weight disappearing from his shoulders.

"That's a dark thought" Chuck said while Nate scoffed. Then he remembered the party last weekend.

"By the way, what's with you and Leo?" Nate asked, taking the joint from Chuck's hand.

"Leo?"

"Leonora Knight, you know who I mean I saw you talking to her at that party"

"Oh.. you mean the pretty princess? Nothing, we were just talking. She is coming to that party Blair is hosting this saturday" Chuck laughed a bit and rolled his eyes. But Nate knew something wrong was going to happened.

"Really? She doesn't seem like the partying type to me" Nate said and took another hit.

"Look, smoke up and seal the deal with Blair. Because you are entitled to tap that ass" Chuck stated and took back the joint before going away from his friend, who had a now terrible feeling in his gut.