Title: Confessions of A Upper East Side Babysitter

Fandom: Gossip Girl

Pairing/Character(s): Nate/Jenny but other characters are apart of the story

Rating: Teen

Spoilers: Completely AU

Summary: ONFESSION NUMBER ONE: The Upper East Side's meaning of a babysitter is someone that watches their younger children while they attend all the fabulous parties, dine at the best restaurants, and go away for a weekend in Paris.

A/N: Hey People! I know, I know, I'm suppose to update Somebody Save Jennifer, but that story is in the process of being read by my beta Jenna. This is a story that I have actually wanted to write long before deciding to do SSJ. I've had this idea for the longest, and decided to write it down. I hope that you all like it :)

Chapter One

"Will you be my girlfriend?". Five year old Matthew Archibald asked, the beautiful girl in front of him, his bright blue eyes twinkling with hope. The girl smiled, blushing just a bit, before putting his arms through the sleeve of his freshly ironed white button down dress shirt.

"Mattie, you know that I'm too old for you", Jenny Humphrey smiled, touching the boys nose with the tip of her pointer finger. She finished buttoning up Matthew's shirt, and sat him down on the bed. Mathew folded his arms stubbornly across the front of his shirt, a small pout forming on his little lips. Jenny had been babysitting Mathew since he was a three, which meant she knew all his little antics and just how to cheer him up when he was feeling down.

Bending down in front of the pouting boy, she brushed his messy brown and blonde hair away from his face. Matthew was like a little brother to Jenny and she hated seeing him upset, although she knew he would be alright after she turned him down for the thousandth time since she'd met him. Matthew was always asking her to be his girlfriend in order to impress the boys he played soccer with on Tuesday's after school.

"Hey, buddy, we're still friends right?". Jenny smiled, her blue eyes meeting the young boys. Matthew smiled, not being able to stay upset for long when Jenny was around him. Mathew nodded. "Good, because after this stupid dinner, we're going to come back here and eat lots of ice cream!".

"Awesome! Jenny, you're the best!". Mathew exclaimed, jumping up and down on the bed with his butt. Jenny laughed softly, before walking over to the closet to retrieve the matching jacket to Mathew's pants. As she doing this the door to Matthew's bedroom door opened softly, a woman peeking her head inside.

"Mathew Archibald, stop that jumping this instance!". Anne Archibald ordered a hint of playfulness in her tone. Mathew stopped jumping quickly afraid that his mother was being serious, and his was going to be in a large amount of trouble. Anne entered the room all the way, a smile displayed on her face to let her son know that she was joking. Mathew quickly caught on and started to laugh hysterically. Jenny watched on as mother and son interacted. Anne began tickling Mathew's sides, his small baby laugh filling the entire room with delight.

"Are you two almost ready?". Anne asked, once she'd stopped tickling the young boy. Anne Archibald was a petite woman, long blonde hair, and wining smile. She was one of the nicest mom's Jenny had met living in the Upper East Side. She really loved her son, always being there fir him. Sometimes Jenny wondered why they needed her so much, if Anne was such a great mother.

"Yeah. I just have to put on Mattie's jacket". Jenny smiled softly, walking over to the bed, and helping Mathew with his jacket. Jenny herself was attending the party with the Archibald family, having gotten ready at home. She was wearing a simple black halter dress, white belt, and open-toed black pumps. Anne called earlier explaining to Jenny it was a black-tie affair, and the color was required.

"Jennifer, there was something that I needed to speak with you about". Anne sounded professional, and Jenny knew that she was about to cross the babysitting line once again. CONFESSION NUMBER ONE: The Upper East Side's meaning of a babysitter is someone that watches their younger children while they attend all the fabulous parties, dine at the best restaurants, and go away for a weekend in Paris. But there are times when these lines are crossed and the babysitter takes the role of nanny. She is to stay with the child for more than a night or day and is to take said child to all their events, such as french lessons, play-dates, school, piano lessons, Spanish lessons, and swim lessons. These things are required the moment the child starts to talk and walk.

"Sure, what's up". Jenny asked, well aware of the fact that she was about to be asked to stay with Mathew for more than just a weekend, and moved in closer to Anne.

"Howie and I have decided to go to the Hampton the beginning of summer, which is tomorrow". Anne explained softly, playing with the diamond ring on her left hand.

"Wow. I could never imagine the Captain in a Speedo, but have fun". Jenny laughed jokingly and Anne soon joined in.

"The thing is, I need you to stay with Matt while we're gone, which will be for two weeks". It was then that Jenny realized why the Archibald's needed her so much. While Anne adored her son, she loved the idea of being away from him for a long period of time much more enjoyable. She could live a motherly-duty free life, without responsibility and a son that required so much of her time.

Jenny glanced over her shoulder at Matthew, instantly feeling sorry for the young boy, then back at Anne with a smile. "Of course".

Anne smiled, clapping her hands together. "Great. Howie and I will be leaving right after the party. You will proceed with Mathew's schedule just like always". With that, Anne exited the room.

"But what about your summer classes?". The other girl on the telephone line asked Jenny. It was late in the night, and Jenny was alone in the Archibald's lavish living room area, Mathew asleep on the couch at the far end of the room. The little boy had fallen asleep while the two of them were watching Finding Nemo, Mathew's favorite movie. Jenny herself adored the movie, a touching family movie that would make anyone between the ages of six and thirty-five cry like a baby.

"Classes don't start until after the Archibald's get back, which means I'll still have time to go". She explained to her friend. Jenny was a sophomore at NYU majoring in Fashion design. It was a dream of hers to become famous for her unique way of designing clothes.

"Bullshit! You and I both know that they are going to con you into babysitting the kid, so that they could jet off to Paris for the summer". The girl continued her rant.

"Agnes, everything is going to be fine, and I love Mattie, which means I don't mind babysitting him", Jenny argued.

"No, Jenny, babysitting means watching the kid while they go to a party for the night", Agnes explained, talking a little too loudly into the receiver. She was probably talking loud so that Jenny could hear her over the sound of the busy city around her. "Not watching the kid for two weeks while they lay out in the sand at the fucking Hampton".

Jenny pulled the phone away from her ear, as the sound of loudly honking horn took over the receiver. "Aggie, I will take those summer classes and I will tell the Archibald's all about it when they return next week and they will totally understand".

"Jen, you are so naïve. Those people could give two shits about your life". Agnes continued, crossing the street into traffic. She was so caught up in her conversation with Jenny that she didn't notice the cab coming her way until he honked his horn. They guy screamed something at her, which Jenny couldn't quite catch. But she did however hear Agnes's reply. "Fuck off, you idiot".

"Agnes, I'm hanging up before you get killed". Jenny laughed, before snapping her cellphone shut. She looked around the room, the TV, now rolling the credits of the movie, and Mathew's snoring becoming just a little bit louder. Jenny looked over at the clock, seeing as how it was really late. She walked over to the couch, scooping Mathew into her arms and walking towards his room.

After the little boy was tucked in nice and neat, Jenny walked quietly to her own room. When taking the job as Mathew's babysitter, Anne warned Jenny that there might be late nights where she would have to sleep over, until she and the Captain returned home in the morning. Which is why she'd given Jenny her very own room. The Archibald house was big enough for a family a eight, and Anne explained that they had more than enough room for her. Growing up, Jenny never lived in a house like the Archibald's, in fact, Jenny hadn't lived in the Upper East Side growing up. She grew up a Brooklyn girl, living with her father and brother in a three bedroom loft. She did however attended a plushy high school, Constance Billard. But other than that, Jenny was far from Upper East Side Royalty. There were times when Jenny couldn't help but envy the off-spring of the rich and famous. They had so many opportunities, but took them for granted, knowing they had a trust fund and rich parents to rely on.

On her way to her room, which was down stairs just pass the kitchen, she heard a faint noise. Jenny assumed that it was nothing until she hear it again only this time a little bit louder. She jumped softly, realizing the noise was coming from near the front door. Like all those stupid people in the horror movies, Jenny moved towards the noise, being sure to grab the umbrella off the rack near the coat closet. Jenny held the umbrella up in a striking position as the front door opened and in came two unidentified profiles, that looked like one. with ought thinking Jenny swung the umbrella hitting one of the two people over the head. Take that! Jenny thought triumphantly as she continued to whack the two burglars.

One of the burglars however was pretty strong, because he grabbed the umbrella, pushing it and Jenny against the wall. The other burglar ran out the door, wearing what sounded like high heels.

"Who are you?", Jenny demanded to know, although her voice was shaking and she felt like she was about to cry at any given moment. The burglar pinned both her arms above her head and had his body pressed tightly against her.

"I could ask you the same thing". The burglar countered, as if he was in the right. His voice was deep and it sent a shiver down Jenny's spine. There was something off about this burglar that Jenny didn't like one bit.

"Me? I'm not the one breaking into someone's house". Jenny struggled to break free from the burglars grasp, but she was having no such luck, this guy was too strong for her.

"How can I break into my own house", the burglar sounded amused. It was then that Jenny realized, just who this burglar might be.

"You're not…". The burglar let Jenny go, then switched on the light that was next to the door. Jenny's breath caught in her throat. This was one of the hottest burglar Jenny had ever seen! Not that she'd seen many.

"Nathaniel Archibald".