Good morning all you Upper East Sider's and welcome to the first glorious day of summer break! The sun is shining, the heat is sweltering and what's that…? The infamous S, B, N, C and Lonely Boy are fast approaching the Upper East Side? Yes, you heard me right boys and girls.

So let's recap the last time we saw our all time fave fivesome.

When we last saw S and Lonely Boy her bags were packed and heading to Brown and his to Dartmouth. S and Lonely Boy had finally decided they weren't meant to be and parted their separate miserable ways in search for some well needed solitude away at college.

Last time B and C were on our radars they weren't on each other's. B and C couldn't manage to work things out which left C and his philandering ways leaving early to attend Princeton and B saying her goodbyes to her BFF S, earlier then planned to jet off to Yale like she had always dreamed.

N, who initially was being forced into going to Dartmouth but really wanted to attend USC finally got his wish and was accepted. Last time we saw N he was single, alone and hot. We doubt much has changed, we think he's still hot for S. Maybe this time around S and N will get together.


Blair flipped open her new sidekick and glanced over the news on Gossip Girl. Her eyes rolled as she saw her name connected with Chuck's. They were so 7 years ago.

"Dorota where's my mother? She said she'd be here when I got home." Blair demanded.

"Miss Blair your mother is running late from business meeting." Dorota cowered before Blair.

"Of course she is. I haven't seen her in 2 years and she still can't make it home on time to see me."

Blair stuck her hand out in front of her and admired the diamond ring on her ring finger. It sparkled immensely. A lot had changed for Blair in the past 7 years.

Before she left for college all those years ago Blair and Chuck had tried numerous times to work out but they never could and in the end Blair couldn't do it anymore and told Chuck it would never work. Naturally he brushed it off and ran away to college early. A rumour circulated that Chuck and broken Blair's heart and she then just couldn't wait to get away, so she left early.

In her first year of college she dated 3 guys, each just a cheap replicate of Chuck.

The first guy, Peter Black was a jerk. Blair met him at a party one night where he sweet talked her into bed and although she enjoyed the much missed smarminess he often was found cheating on her and Blair Waldorf would never take that.

The second guy, William Costa was a secret. Or rather she was his secret. He was thought out to be the top of the league at college and predictably already had a girlfriend when Blair met him. At first it didn't bother her, what she liked about William was the way he resembled Chuck physically and it only got too much when she passed him in the hall one day and said hi and he mocked her in front of his friends. Naturally, she spilled their secret and ruined his life at college.

The third and last guy, Lance Williams was a complete sex God. He knew things Blair had only known Chuck to do. Lance could just look at her and her panties would dampen. It wasn't love, it wasn't even like, it was lust, the pure, raw passion that he elicited from her every time they were together.

After Lance Blair swore she would stop dating until after college. That was true until she was half way into her third year of college and met Blake Parker. Blake Parker was everything that Chuck wasn't and in a way resembled Nate. He was attractive and intelligent, sexy and suave, clean and elegant. Blake Parker was perfect.

Blair and Blake dated for three and a half years before he bent down on one knee during a cruise and proposed to her. It wasn't even a question to her, she knew she would say yes. He was her perfect.

Back in the Waldorf penthouse apartment, the elevator doors clicked open and out stepped the older Waldorf.

"Where's my little girl?" Eleanor asked, smiling and out stretching her arms as she spotted Blair.

Blair ran over to her mother and hugged her tightly.

"Mother I have some wonderful news! Blake and I are getting married!" Blair said as she flashed her diamond ring.


Serena watched as the other cars drove past and the buildings that passed and wondered where they were going. Unlike Blair, Serena hadn't been home in seven years.

When Serena and Dan finally broke it off for good and both set off for college Rufus and Lily finally took liberty in getting together and were married privately, just the two of them, Eric and Jenny. Once Serena had heard she was afraid to go home. All she could think of was about running into Dan.

At college Serena consecutively dated. There weren't 3 guys, or seven or even 10. She in fact had lost count. Sometimes she'd just pick out things about them she didn't like that were barely noticeable and tell them it would never work or sometimes she would compare them to Dan and then break up with them because they couldn't compare.

She knew it was stupid and that she had to let go of Dan. In her 6th year of being away from home Serena finally found it in her heart and head to let go of him. She was free but still didn't find anyone she was truly interested in.

The black car that was sent to pick her up from the airport pulled up outside a tall, old building. As she got out the driver grabbed her bags and handed them over to doorman who directed Serena inside and to the elevator.

"Your mother and step-father are waiting for you on the second floor." He said.

Serena thanked him and travelled up to the second floor. As the doors opened, her heart raced until she stepped out into the room only to find Rufus, her mother and her three year old half-sister, whom she'd never met.

"Serena." Her mother said, always poised and perfect.

"Hi mom." She paused. "Hi Rufus."

"Welcome home." He said.

The little girl Serena had assumed was her half-sister smiled brightly up at her. She was almost identical to what Serena had looked like when she was 3. Serena bent down to her knees to the small child and extended out her arms.

"Hi, I'm Serena your big sister." Serena said.

"I am Isabella."

"It's nice to meet you Isabella."


Dan unlike Serena had travelled back home many times over the seven years he lived away from home. At first he was apprehensive about going back in case he ran into Serena at the house. But when Jenny called him and told him the good news about his father and Lily marrying he had to fly back to congratulate them.

Also unlike Serena he had met Isabella several times.

Dan arrived at the immensely huge apartment his father now lived in and waved to the doorman.

"Hey Roger are they here?" Dan asked.

"Certainly Mr Humphrey. Second floor, you step-sister just arrived home not too long ago."

Dan's heart pounded. Serena was home? Serena was home. As he was getting in the elevator he saw Jenny running towards the elevator.

"Hold the elevator!" She yelled, heaving rolls of material.

Jenny got in the elevator and dropped the material wrapping her arms around her older brother.

"I'm so glad you're home." She said.

"Yeah, me too." He replied.

The elevator pulled to a stop and slowly, painfully slowly they opened and he saw a flash of long, blonde hair that could only belong to Serena Van Der Woodsen. Jenny heaved her rolls of material inside the room and dropped them again to greet Serena.

"Hey!" She squealed, excited to see her step-sister for the first time in seven years.

"Jenny! Wow, I love the hair and that bag, that's cute."

Jenny blushed. "Oh thanks."

Dan slowly walked towards his family.

"Hey." He spoke.

Serena turned around. Her facial expression dropped.

"Hi Dan."


More handsome then seven years ago Nate stepped into a high priced restaurant with a beautiful black haired beauty in tow. His mother alone sat at a table sipping a glass of iced water waiting for her son.

Nate like most of the others had rarely come back to the Upper East Side in the seven years before today. His mother always insisted she fly out to see him and even when Nate got married and wanted the wedding in Manhattan his mother insisted he have it in California.

"Hey mom." He said, smiling.

"Oh Nate!" She smiled, getting up and wrapping her arms around her son. "And Amelia, you look lovely." She said.

Amelia Heart (Now Archibald) was Nate's lower class wife who had never grown up on the Upper East of anything. Her clothes weren't designer, her hair wasn't cut by someone who had just recently done Paris Hilton's or Victoria Beckham's. She was from California and met Nate at a coffee shop one morning when she accidentally spilled her coffee all over his Versace sweater.

It was love at first sight, the two dating for 4 years before Nate proposed in private at his Californian apartment and then married in a small service on the beach with both of their families present.

"It's always lovely to see you Anne." Amelia spoke softly as she seated next to Nate at the table.

While Nate enjoyed college at USC he never really got the hang of it and in his third year he quit and started his own business with his trust fund money. At first business was failing until he employed a man by the name of Samuel Colt who sent business booming and made Nate the youngest rich male in all of California.

Nate and Amelia now owned a mansion on a Californian beach, a house in Italy, an apartment in London and an apartment in Manhattan.

"Mom, we have some news to tell you." Nate grinned, grasping his wife's hand.

"Yes dear? What is it?" Anne asked as she looked over the menu.

"I'm pregnant." Amelia beamed.


Chuck most unlike the other four was not back in town for family. No, Chuck had no family. His father was dead, his mother was dead and he had no real siblings. Chuck was back in town for business and business only because apparently his incompetent business associate in New York couldn't handle some deal with some company and Chuck had to fly out from his mansion in Maine.

He like Serena had not been back to the Upper East Side in seven years. Sure, he had traced the outskirts secretly, kept in touch with a few businessmen from around town but other than that he cut off all ties towards the place he once loved so much.

There was nothing left for him in New York. His family were all dead and the only other people who had ever meant something to him had moved to various states around the country. He had no place being back.

Chuck entered his New York offices and immediately made his way to the top floor where his business associate was waiting for him in the meeting room. He barged in, unannounced, rudely and loudly. He didn't much care for politeness, he didn't even need the money he was making he did it to keep entertained.

"Mr Bass." Henry, his business associate said as he rose from his seat

"Sit down Henry. I want to get out of here as quickly as possible." Chuck spat.

Sitting across the table from Henry was an immaculately dressed man who reminded him somewhat of Nate. He was cleanly presented, a navy cashmere sweater adorning his torso. It was summer, what the hell was the guy doing with a cashmere sweater on?

"Who the hell are you and what do you want?" Chuck asked rudely.

"Mr Bass this is Blake Parker the guy I was telling you about on the phone. He just bought the twin set of apartments I showed you." Henry said.

Blake rose from his seat and extended his hand. Chuck reluctantly shook Blake's hand and then sat in his chair.

"What is it I can do for you Mr Parker?" Chuck asked.

Blake slid a folder over to Chuck and then started speaking.

"Mr Bass I've been in business for a few years now and I've made a lot of money of a number of things. Now what I'm here for his a proposal. The Winchester buildings are the two oldest building on the Upper East Side of Manhattan and I just purchased them a few days ago. Inside that folder you'll find my ideas for those two lovely buildings. I'm here to propose to you a business partnership, a once in a lifetime chance. I rarely work with others, I prefer the solitude. But Mr Bass these two buildings are calling for some money and I alone have the money to do it."

"Then why do you need me Mr Parker?" Chuck asked, flicking over the folder.

"Well, see, I could make these buildings beautiful and make an immense amount of cash off them by building hotel or something but I think that by partnering up with you, having two intelligent men working on one huge project we could make these buildings amazing."

"Mr Parker, I don't need your charity, I'm the wealthiest 25 year old in America. Besides that I hate New York. Had you have proposed this same proposal anywhere else I might have said yes."

Chuck rose from his seat.

"I assure you Mr Bass New York is not my perfect place either. My fiancé and I live Connecticut and it's quite an inconvenience to fly out here but I don't think this could work elsewhere."

Chuck looked down at his watch. He had no where else to go, no where to be, no where he was itching to go. He just sometimes looked down at his watch and wondered about things.

"Draw up some contracts and I'll have my lawyers look them over. If they suit me, then you have yourself a deal Mr Parker. But let me tell you one thing, managing a business in New York from Connecticut won't work and I advise you to talk to your fiancé about this before you make any decisions. Unlike you I have no one to take into consideration and I can sign those papers as soon as they're drawn up."

Blake stood up and shook Chuck's hand.

Chuck may not have family but he had his business'.

"Have a good day Mr Bass."



S walking into her new family home where Lonely Boy too will reside when he comes home for family visits. S and Lonely Boy under the one roof? Could things get hot and steamy for the pair or is the romance finally dead?

Also spotted.

B with a diamond ring on her finger. Could she be engaged? Or is she flaunting an imaginary husband?

N having lunch with mom and…wife!?

And C back in town for what exactly? We assume business but maybe he's heard B's back in town.

You know you love me.


Gossip Girl.

Alright, so this (for all of you who are confused :P) is set after they go to college. Obviously it's been seven years and they're all back in New York for various reasons, unknowningly to the others. There will be a few original characters but I don't think I'll make them major participants. There will be a bit of Chuck/Blair and Dan/Serena, maybe Nate/Serena or Nate/Blair I don't know yet. Review and let me know if it's worth continuing.