A young woman stood outside the station, turning her head left and right before anxiously looking at the time. It was highly unusual with someone of her status to be standing around but at least the actual driver was with her. She smiled brightly and waved frantically at the new arrival. The woman's curls were perfectly in place as she waltzed towards her friend; the years in Europe did well for her. Clad in red, the brunette followed the bubbly woman in pink as they made their way to the car with the driver following the young women.

"Blair how long has it been?" The blonde, by the name of Serena, squealed at her friend next to her. The much more composed other shook her head at her friend's antics. She missed New York.

"Too long is what you would say if you were in my predicament, but me being more practical it has been two years." Blair Waldorf replied while Serena held her hand the entire way to the Waldorf Residence. Blair Waldorf was on her way to be the epitome of class in their society. The beauty had a lot to live up to. Her mother was queen of the city when she had been Blair's age; her grandmother was labeled the most beautiful and had the eyes of an enchantress making anyone bend to her will. Blair did not inherit the cold, alluring eyes of her grandmother nor her mother's blinding smiles. Blair always made sure she excelled others' expectations, which differed immensely from her bubbly best friend.

Serena van der Woodsen was part of one of New York's oldest families and most prestigious. There were more expectations but instead of following her friend's path, the blonde chose to ignore society's orders focusing on other important aspects of her life instead of living up to the older generations' expectations and requirements. She embraced the new fashion of shorter skirts and casual flirting of men easily, much to Blair's disapproval. Serena was simply carefree and happy even if she was frowned upon with the upper elite.

The two made their way to Blair's family residence as they caught up with the last two years of their life. Serena spoke of the nightlife she became part of once she turned sixteen with their other friend, Nathaniel Archibald, joining her shortly.

"It's so much fun, the dancing, drinks all around, no one caring what you do or if you make an embarrassment out of yourself, best of all no old ladies who act all high and mighty simply because they saw me giggling with their grandson." Serena finished as they entered the home to the small dinner being held in Blair's honor. They were greeted by servants including Blair's personal maid, Dorota. Blair led her friend to the bedroom she had not seen since she was sixteen and shook her head with displeasure at her friend's activities.

"What do you think would happen if anyone saw you there? Tell Nate I said the same thing." Blair scolded while Serena rolled her eyes at Blair's fear.

"So what if they do. Blair, I want to have as much fun as I can before those hags ruin it." Serena expressed, sitting on Blair's bed. Blair examined her room, making sure no one has entered her private chamber only doing so to clean. So far the help was living up to her expectations.

"Why don't you come with me tonight?" Blair scoffed at Serena's proposal as the servants came in with suitcases and began to unpack.

"I'm not having this discussion with you the minute I come home. You know how I feel, I told you how I feel when I wrote letters to you. I am not your mother so I will not try to control you, just be careful." Blair said as she left to find a more appropriate dress for this evening. Anything under her parents' expectations would not be acceptable.

"B, I have to go." Serena said, getting up while she did so, as Blair quickly turned and gave her a questioning look.

"Why? Your family is coming and Serena, I just came home and you're leaving within the first couple hours we've seen each other?" Blair asked as Serena looked down at her feet, feeling the guilt begin to pour in; however, she and Nate have been going to these nightclubs for the past two years every week. It was tradition that Blair was not part of nor would she approve.

Seeing her friend's emotions flicker back and forth in her eyes, she sighed loudly, "Fine, we'll spend some time together tomorrow, go dance and drink to your heart's content." Serena grinned and squealed before pulling Blair in her arms.

"Thank you and Blair please think about my suggestion." Serena called before running off to change into something slightly shorter to match the other vamps and flappers at the club.

Blair descended taking in the sight in front of her. Her mother had out done herself, but Blair had to leave in a matter of months so she believed this was quite unnecessary; however, the thought was nice. If only Serena could be here, even her family was here. Blair couldn't help but smile as her grandfather, James, enveloped her in a hug.

"My dear, you have grown." He said affectionately as Blair placed a kiss on his cheek.

"She has not, she's wearing heels now." Blair turned at her grandmother's voice. The elderly woman kissed Blair's cheeks before pulling back and examining her granddaughter. She frowned slightly making Blair's insides churn, before she watched fingers lifting a curl from behind her ear and letting it fall.

"There, now you're perfect." Her grandmother, Rose, said smiling at the young lady her granddaughter was slowly becoming the lady she was expected to be. She was not disgracing herself like the new kind of women that existed. She knew France was a good idea.

"Blair darling, I have missed you." Blair turned at her mother's voice. The woman stared affectionately at her daughter, taking Blair's hands into her own and hugged her tightly.

"I told you France was a good decision." Eleanor Waldorf told her husband and Blair's stepfather, Cyrus. The shorter man smiled at his stepdaughter and joined his wife at the table. Blair noticed the van der Woodsens and the Archibalds sitting at the table already; however, Serena and Nate were absent.

"I thought Serena would be with you. She picked you up from the station." Lily van der Woodsen said as Eleanor nodded in agreement.

"Serena was here. I saw the girl with you when you both were coming back to our house, where is she?" Eleanor asked Blair who forced a smile, mentally cursing her friend for making her lie to her own mother.

"She had a date." Blair lied as the women rolled their eyes or scoffed at her answer. It was partially true; she was going with Nate, which was in a sense a date, only they were going to the underground clubs instead of a restaurant or a walk around the city.

"That girl is driving me up the wall, she is at that age." Lily exclaimed to Eleanor who nodded sympathetically.

"Where's Nathaniel and Lily where's Eric?" Cyrus asked.

"He's with his cousins; he has been spending a lot of time with them these couple of years." Anne said proudly as Blair's grandparents nodded in approval. If only they knew what he did after those supposed visits.

"Eric is in the country this summer with his father. The divorce was hard on him." Lily explained as Eleanor placed her hand on her friend's sympathetically.

"The Vanderbilts, that's good for young Nathaniel. His grandfather will help him find a fine wife." Rose gushed. Blair sat through the entire evening making small talk with her family and wondering what her friends were doing.

Serena giggled with the other women, twirling around to the next quick tune. This was why she went out every week for the past two years, Serena wanted to be herself. Being part of that upper elite was challenging and sooner or later you find yourself becoming your mother or your grandmother. You find yourself stuck in old traditions and then you'll be looking in the mirror frowning at the number of wrinkles, even though it was barely anything compared to the other women outside of their circle, who actually had hardships.

Nate pressed his lips on another girl's hands once the music stopped. She giggled and blushed before he handed her to another man. He smiled, this was the life. He loved the life of no expectations, now worries, no maintaining a reputation, and lastly no looking for a wife. He wanted to be able to attend speakeasies where he occasionally interacted with a mobster, flirt with women who knew he was not promising marriage. He grabbed the hand of the women that just ran past him and led her away from the dance floor and towards the bar.

"Having fun?" Nate asked his longtime friend as the blonde giggled while nodding her head.

"You ask me that every week and my answer is still the same, yes." Serena answered smiling sweetly before leaning up and kissing his cheek. Nate laughed and grabbed the drink from her hands.

"Enough unless you want your mother to suspect something." Nate lectured and placed the drink on the counter.

"You smell like cheap perfume Nate, how many women were you with?" Serena scolded lightly while Nate blushed, but simply clapped his hands as the music ended. Serena smiled and turned around to applaud the musicians and watched as a young man took the stage.

"That was a marvelous performance gentlemen and I thank you as well as the audience for making tonight an absolute splendor. I think the crowd as well as I would love it if you will join us next week." He said while clapping his hands as the crowd joined him.

"How about one more before the night ends?" Serena cheered loudly as the band nodded and began to play. He got off stage and quickly made his way around the room, greeting individuals, about to finish his round before he felt himself be yanked back by his arm. He turned to see the beautiful blonde and her companion staring at him.

"I told you they were fantastic." Serena smiled as the man straightened his tie and smiled at his friends.

"Serena I know and thank you for the suggestion." He mocked bowed as she slapped lightly on his arm.

"How are you two enjoying the night?" Charles or as everyone called him Chuck Bass asked remembering his job description.

"It's fantastic, but come on even the great host has to have some time with his friends." Nate sat down Chuck on one of the barstools and ordered a scotch.

"Everyone is my friend or at least that's what the job description says now excuse me." Chuck replied as he drank it quickly before running off when he noticed some women begin to argue.

"Come on, the night's about to end." Nate took out his fob watch and ; it was close to 3am. Serena remembered what she was supposed to do and ran to Chuck once he settled the women down and passed them back to their respective groups.

"Can I bring a friend next week?" She asked while she placed her hands together to plead as well.

"As long as she doesn't say anything to the last generation, sure. Serena you know the rules and we have some important people coming next week so make sure she follows them." Chuck warned while Serena nodded quickly, not hearing what came after once he gave this approval, and kissed his cheek, "Thank you." Serena ran off back to Nate.

"I'm serious Serena." Chuck yelled as Nate shot him the thumbs up.

Chuck made his way to his apartment and was relieved he got out before sunrise. Tonight was busier than usual, but it was worth it when his pay came in. He took off his jacket and hung it on the old hook before turning around to see his mother on the couch fast asleep. Chuck ran his hands through his hair and sighed. She had waited again.

"Mother." Chuck said quietly as he watched her eyes slowly open.

"Charles, did you just get home?" Chuck nodded as he placed his hands on his mother's shoulders as she began to get up.

"Mother, stop. Did you wait for me all night?" When he got no answer, he sighed and began to lead his mother back to her bed. Once she was settled, he sighed, "I told you to stop waiting for me. You're already sick and the doctor said you need rest."

"It's dangerous, what you do almost every night and next week will worry me even more, the mobs. Please be careful." His mother begged, but how does a son tell his mother no matter how careful he is being, in his line of work something may happen.

"I always am." Chuck replied, kissing his mother's cheek watching as she drifted off to sleep.

Chuck yawned, walking towards the kitchen and the only clock in their home. He had enough time to sleep for a couple hours before he had to start preparing. Chuck began to lay out his clothes for that evening, thanking the owners mentally for giving him the appropriate wardrobe.

Tonight was going to be hectic, but that's not new.

Blair stepped out of the car glancing at Serena's home. She smiled remembering the memories of her childhood at this home before her; she smiled fondly thinking back to Lily van der Woodsen's numerous husbands.

"Miss Waldorf." The butler greeted, leading her to Serena's room. Blair opened the door to see her best friends still unconscious; Nate on floor near the closet and Serena splayed out on her bed wearing the clothes the night before.

She frowned slightly at the sight; this was why she refused to be in such establishments. She walked to Nate and kicked him lightly on the leg. Nate stirred at the forced movement; it was a long night with only a couple hours of sleep. He pressed his face against the plush carpet…wait Carpet? Nate's eyes opened feeling carpet beneath him instead of a soft, warm, bed. He rubbed his eyes gaining some clarity and jumped when he noticed Blair's figure towering above him, looking pristine compared to his scruffy appearance.

"Blair, good seeing you again." Nate greeted, pushing himself up, until he noticed his current location. He looked around to see his friend sleeping on her bed in last night's dress and makeup smeared on her pillow.

"Long night?" asked Blair, smirking at her friend's current state, taking in his disheveled clothes with the strong aroma of cheap perfume and a lot of liquor.

"Be glad I'm not authority Nathaniel. What would mother think?" Blair held out her hand pulling the young man from the floor. Her nose crinkled at the sight, the pink lip imprints on his white, once crisp, shirt.

"Miss Waldorf, ." Both turned to the timid voice behind them, the youngest maid of the Van der Woodsen household, Jenny Humphrey. She clutched the racks of clothing in her arms, trying to avoid the scrutinizing gaze of Miss Waldorf at the same time doing her job. She hung the newly pressed gowns in their positions before making her way tidying the room, making sure to work fast but not disturb her mistress.

"Wake her up, will you Jenny." Blair demanded watching as the fifteen year old nodded quickly, making her way towards the blonde's bed.

Blair walked down the marble stairs, awaiting the arrival of both her friends. Nate had quickly gone to the bathroom once one of the other servants had presented him new clothing. So this was a frequent past time of his. These were times she wished she had never gone to school abroad, she was left out of her friends' traditions as of late and joining in was unacceptable especially with all eyes on her waiting for their future queen of the city to mess up and bring shame upon herself. No, she had more self-control.

Nate waltzed down the steps, running his hands through his hair as he nervously approached Blair. Serena had asked him to help her convince Blair of one night of fun, utter bliss, no consequence, but Blair's mind did not operate in such a way. Blair was always the stickler for rules, scolding him when he ran in the mud at Central Park when they were seven, lecturing when she found him in the kitchens communing with the chef's daughter, she never damned the consequences.

"That's better." Blair smiled, pulling her freshly scented friend in her arms.

Nate was surprised at her reaction especially after she had found him this morning, but returned the gesture, "I have missed you." Blair let go smiling at his admission before leading him to the dining room for breakfast.

"Sorry for missing dinner last night." Nate said grabbing the pastries that had been laid out since nine this morning. They were still warm, sort of. Blair sat on one of the sofas with her own assortment of fruit.

"It's fine, your mother said you were with your cousins last night." Nate froze when he was about to bite into the pastry and slowly placed it back on his plate, looking back at Blair, who was stirring her tea.

"I was technically." Nate told her, he was with his cousins only he never talked to them last night and only saw glimpses of them at the club.

Blair nodded and raised an eyebrow at his answer, "I don't understand why you and Serena love it so much."

"Well, Serena convinced me to come and I don't know it just became a weekly thing." Nate explained, and took a sigh before walking around the table to her seat.

"I know what you're thinking." Nate began slowly, sitting down beside Blair, who raised an eyebrow, but motioned for him to continue.

"There are a lot of risks to what we've been doing for the last two years of our lives, but Blair the feeling of not having a care in the world in so riveting." Nate began while Blair understood what he was trying to explain.

"No"

"Blair come on."

"No." Blair answered again silencing him with a look, as Serena finally came down looking refreshed.

"Did Nate talk to you?" Serena asked smiling brightly, until Blair gave her a hard look.

"Serena no." Blair finalized as Serena ran to the other empty seat beside Blair, tugging on her hand like a child.

"How about just this once, next Friday, and if you immediately hate it and want nothing to do with it I'll never speak of it again, but please this is probably our last opportunity of fun before we have to get married or something." Serena begged and motioned for Nate to help.

"And I promise you won't get caught, we are experts at sneaking through the night." Nate tried to convince, trying his best to look innocent.

Blair looked at her two friends and rolled her eyes. They didn't understand the risks especially with what her parents had been preparing for her. Nate and Serena listened to their families, but they weren't obedient. They did their heart's desire whereas Blair was raised to put her heart aside and look towards her bright future.

"Fine."