AN: The story of TNG of Gossip Girl. Fair warning if you are a fan of Dan Humphrey, you may want to go back now. However, canon pairings include Chair and Serenate.

Enjoy.

Chapter 1: The (not so) Sweet End of Summer

Spotted: H, stumbling into his limo, drunk off his Bass on his way home. Are vampires in this season? Henry seems to think so. He hasn't been seen in daylight since his return to New Haven, only in the dark in clubs, the hotel bar and in his room by sunrise. Is he allergic to the sun, or memories of his ex?

Henry scowled at the blast, sitting on the floor of his hotel room, a glass of scotch in one hand, his phone in the other. He thought New Haven would make it easier to get over her. But Gossip Girl was dead set against that. He hadn't even done anything wrong. Accusations of infidelity, she refused to believe him. Maybe he was the son of the once great hedonist Chuck Bass, but that didn't make him a cheater. His father had changed, why couldn't people simply believe that he didn't have to, he was never like that.

He had tried to convince her. He'd said he loved her. The only girl who he'd loved tossed out what they had. Once upon a time he's decided to stop playing games and start winning. What happened only proved that it was the biggest mistake he'd ever made. What had he been thinking?

You couldn't win the game like that. You could just keep playing until the other person submitted, that was winning. Mutual submission results in a draw. A draw is worse than losing. He'd rather have kept playing till he won the old fashioned way.

Flashback

"Ash," he greeted happily as he entered the penthouse. She looked upset. "Hey, what's the matter?"

Glancing up from her phone, he could see her eyes aflame. That was never good, he hadn't seen that look on her face since…

"What the fuck, is this, Henry?"

He looked at the phone. At the picture that so enraged her. It was him, at the opening night of Van Des, Bass Industries newest club. Henry looked happy with a drink in one hand, surrounded by burlesque dancers. He read the post below, not knowing what to expect if it made Ashley this upset.

Spotted: H at Van Des. Enjoying himself, a little too much, maybe? My sources tell me he spent an awful lot of time in the restroom, following out a fellow dancer. What about A, Henry? Or have you moved on to bigger and burlesquier things?

He glanced up from the post, looking incredulous, Ashley still looked upset and angry at the same time.

"You don't really believe this do you?" She said nothing. "Come on, Ash. This is Gossip Girl. You can't really expect that all her sources are accurate."

Her eyes dropped down to her feet and he stepped closer. "Hey, look at me. I love you, only you okay. Nothing happened."

She began to shake her head quickly. "No, no, Henry. I saw the pictures okay," she held up her phone to show him those of him walking out of the restroom with the dancer in front.

"Those don't mean anything. We just walked out at the same time."

"Are you seriously saying this?"

"Yes! Yes, I'm saying it because it's true!" Henry was beginning to lose his temper. They'd been going out nearly four years and all of a sudden she didn't trust him? What was happening?

"I can't do this Henry." She broke the silence.

"Can't do this? Can't do what?" his anger almost dissipated into panic in that moment. "Us?"

"Henry you should go."

"I would never do this to you. You know me," he felt his voice drain away. "I could never do this, especially not to you. I would never hurt you like this, you have to believe me," his voice became even more quiet. "Why don't you believe me?"

No response.

"Ash-"

"Please!" she snapped before growing softer. "Henry...maybe we should just...be apart."

"You wanna throw away everything we've built over a stupid rumor?"

"Henry!" she nearly yelled. And then her voice grew quiet again, as if a silent apology. "Leave. Please."

He took a step back and looked at the ground. If she was willing to throw everything away over this, then clearly she didn't think they were worth fighting for. He wasn't going to do everything in this relationship, himself. It took two people to make it work and he wasn't going to do it by himself. He was twenty years old now, he didn't have time to play these games and more than that, he was Henry Bass. He wasn't going to beg at her feet like a dog.

"Fine." Henry said firmly as he headed towards the elevator, a dull ache present in his chest. "Fine," he mumbled as the doors opened, he paused before stepping in to take one last look and say one last thing.

"Clearly our relationship isn't something worth salvaging."

The doors closed as he stepped in and taking a deep breath, he held himself in. He wouldn't cry, he wouldn't tear up. If she didn't want them, then screw it! Neither did he.

That has been two months ago.

But in the limo, at home, on the flight back, in his hotel room, the dull ache still resonated in his chest. No matter how hard he'd tried to drown it out. The reminder only filled him with copious amounts of anger as he hurled the phone against the wall, will a loud thump and shattered it into a hundred pieces.

Just like his heart.

No, he wouldn't think like that. Taking another swig from the bottle, Henry slowly felt the pain dull away. It would be back soon, but he could keep dulling it. There was no full proof magical cure. Only constant treatment would heal his pain.

The darkness in the room was actually comforting. The drapes shut. The door closed, the lights off. Nobody could see him, nobody could hurt him. He would lurk in the shadows and win every game he played. The light exposed you, left people to see your weaknesses, your vulnerabilities. It was a mistake he'd never make again, going to the light.

Draining the last of the bottle, Henry rested the back of his head on the coffee table and stared up at the ceiling, his eyes gradually growing shut. So he didn't hear the footsteps approaching the door, its opening. He didn't notice anything until….

"Rise and shine, nephew!" A booming voice called as the curtains were pulled open, exposing Henry to vast amounts of sunlight, causing him to shield his eyes.

"What the hell?" Henry groaned. Not moving from his position. However after blinking several times, he caught sight of the sandy blonde hair, devilish face and mischief in his eyes, Henry only knew it could be one person.

"Milo," he groaned.

"That's Uncle Milo to you, Hen," he smirked. He began directing some of the maids to clean this and that up, hit the lights, clear away some things.

"Don't call me Hen!" he snapped. "I'm Henry Bass, nobody else."

"My bad, nephew," Milo replied unapologetic. Henry glared. "What? I am your uncle."

"Step uncle."

Milo scoffed. "Look, I'm taking time off Kyan for this. You need help, I'm helping," he picked up the empty bottle of scotch lying next to Henry on the ground.

"Go back to New York, to your club and leave me alone," Henry scoffed. He didn't want other people around. No one could see him like this, especially not Milo Sparks. Least of all Milo Sparks in fact.

"You look like shit."

"Look who's talking, Sparks."

"Get in the shower, Bass." Milo gestured to the bathroom.

Henry stayed and pouted like a petulant child. Milo took a few struts into the bathroom, Henry, assuming he'd given up, stumbled around, trying to find another bottle of liquor as Milo proceeded to pour water on his head.

The cold instantly took Henry put of his state and enraged he jumped to his feet.

"WHAT THE HELL?"

"Good," Milo smirked, feeling awfully smarmy. "You're soaked, get in the shower."

Henry cursed at Milo under his breath before begrudgingly stepping into the bathroom. Once the door was locked and the water was running for a few minutes, Milo picked up his phone and inputted the number.

"How's it going?"

"He's in the shower."

"That's a good sign," there was a pause on the other end and then, reluctantly, "Thank you for doing this."

"My pleasure," Milo hung up.

Blair put down her phone. The last thing that she had wanted was to have to go to Milo Sparks for help with her son, but he was living in his own world. She knew him, drinking, sex and staying drunk were all that mattered to him while he was like this.

Milo was the only person she knew who could bring him out of it. Blair could be a bitch when she wanted, but she'd always had a soft spot for her children and knew she hadn't had the ruthlessness to kick him while he was down. Even if it was so he could stand up again.

Her memory drifted back to the day he'd returned to the townhouse, utterly upset, fighting back tears. Her heart broke for her son as she'd comforted him like she hadn't since he was a child.

Flashback

Henry took a few steps into the townhouse. His hair was a mess, his teeth had possession of his lower lip, she could tell he was fighting back tears. He looked as if he'd experienced pain beyond his years, yet he looked as vulnerable and innocent and hurt as a small child.

"Henry, what's wrong?" she stood instantly. Chuck, who was next to her, shared an equally concerned look as their son to a few slow steps forward.

"She broke up with me," Henry whispered. "She doesn't think we're worth it."

Blair quickly walked forward and wrapped her arms around her son. He bit back tears once again, burying his head in the crook of his mother's neck –a mannerism like his fathers' –and sank into the hug. Chuck quickly jumped to his son's aid and put his hand on his shoulder and stroked it soothingly.

"I'm so sorry, Henry," he said hushed. "It's going to be okay," he promised.

"Dorota!" she called out, shaking off the memory. "Make sure Luke and Charlotte are ready for brunch!"

"Yes Miss Blair," came Dorota's voice.

"Blair," her husband drawled from his place next to her in the living room. "I don't know about Milo…"

"I didn't want to have to resort to it, but he's been in pretty bad shape, Chuck," she said. He nodded in response. "I want him to get back on his feet, but he's stuck in a lurch."

"Bass men never have been much good in a lurch," Chuck mused.

"You're ready on time," Lucas Bass commented to his sister as she strolled into the kitchen. "That's new."

Charlotte Bass was the apple of their father's eye. With her mother's chocolate curls, a nice body and an impeccable taste in clothing, she won most people over with her beauty and charm. This of course came from an odd yet somehow amazing combination of Blair Waldorf's doe eyes and Chuck Bass' signature smirk. As of right now, she was dressed in white top and pale green bottom dress that went up to her knees, matching heels and of course a matching headband with a bow on it.

She cocked her head to the side and examined her older brother. He, in turn was dressed in a navy blue suit, with a checkered grey and white shirt underneath and a dark purple bow-tie to top of his combination. Lucas was seventeen, just a year older than her and resembled their father stronger than any of them. Her mother had joked that had she not given birth to him, she would believe that Chuck made Lucas on his own.

"And you're drinking," she replied coolly, referring to the glass of scotch in his hand. "I thought Mom said not to drink before brunch."

"Are you going to tell on me?" he quirked an eyebrow. "Besides, of the both of us, I would've thought you should be the one drinking."

"And why is that?" she questioned, with a raised brow.

"Well I figured after your breakup with Lord…what was his name again?"

She shrugged halfheartedly.

Lucas smirked, he knew his sister well enough. "Already forgot?"

"It wasn't worth remembering."

"You're not heartbroken?" he replied sarcastically, knowing full well his sister preferred to use guys as toys or tools. They were fun…for a while and they could help you get what you wanted, but eventually you grow out of them and move on to bigger and better things.

"Mr. Lucas!" Dorota came into the kitchen and snapped at him. "You're mother said no drink before brunch!"

"I'm sorry, Dorota," he replied, appearing genuinely sincere.

"Have you heard from Henry?" Charlotte asked her brother, generally concerned about the eldest Bass siblings well being.

Lucas shook his head. "Just what's on Gossip Girl. He's not coping so well and he won't return my calls."

"Mr. Henry just like your father," Dorota interjected. "Don't know how to deal with heartache. Especially if it's from the right girl for him."

"Hmm," Lucas mused as he moved the glass towards his mouth to take another, sip of scotch and had it promptly snatched away by the family's faithful maid and friend, before he could drink.

"No drink before brunch," she repeated.

"Why? I'll probably need it," he remarked.

"What's the problem? I thought you'd be thrilled to see Nick," Charlotte questioned.

"Oh, it's not Nicholas I'm worried about. It's that stepbrother of his."

Brunch was a time honored tradition in the Upper East Side. Today, the role of hosting had fallen to Mr. and Mrs. Archibald, Nate and Serena, to the Basses.

The Archibald Penthouse was, like its residents, perfect at a glance. Between the polished wood it was what every Upper East household strived to become, yet it had a very "real" feeling to it, it was homey. The Basses entered, dressed perfectly of course and were greeted by Serena and Nate.

After two years of marriage to Dan, Serena had become unhappy with him and the two had gotten a divorce, of course not before they'd had a son together. After a few months, she had reunited with Nate, who at the time had been mourning the loss of his wife Emily for a year and had a hard time juggling his campaign for mayor and being an active father to his one year old son. It wasn't a year before they were married and shortly after, Serena had become pregnant with their daughter. Now, the two were happier than ever.

Seated at their table already, Lucas strolled towards his best friend, Nick Archibald. Nick was Nate's son from his first marriage to California's own 'Golden Girl' Emily Hawthorne. His mother had died when he was just a year old, but since his father had married Serena when he was young, he considered her his mother. Nick had blonde hair and striking dark blue eyes. Dressed in a grey suit and plain black tie, he cleaned up nicely, and his hair was combed back, but still a little ruffled.

"Nicholas," Lucas greeted, taking a seat next to his best friend. "How've you been?"

"Alright," he nodded. "Not ready for school," he admitted.

"I'm thinking about some fresh air," Lucas smirked.

Nick smiled and shook his head lightly in response. "Maybe later."

"Very well. I have my one hitter."

The two had been best friends, practically since they had been in diapers. They had made the perfect duo since they started attending to school in building the perfect, closed circuit circle of friends? Allies? Whatever it was, it was the closest thing St. Judes had to monarchy since Henry's reign as king when he had attended.

Nick was –like his father – the golden boy. Captain of the lacrosse team, handsome, athletic and an all around nice guy from a prominent political family, he attracted people wherever he went. Nick was easy going and friendly could easily take the title of hero without a second thought, which his friend didn't mind at all. No, Lucas left all the hero and white knightly-ness to Nick, who seemed to be perfectly happy with it.

Lucas, on the other hand, held the role of the dark prince with the bright eyes. Embodying the signature Chuck Bass looks, along with the same allure, penchant for manipulation and playboy attitude. While Nick was an all around nice guy, Lucas always had a slight aura of darkness and mischief and scheming present in his eyes. People wanted in because of Nick, but they stayed for Lucas. With that, the pair had been unstoppable.

The two talked for a while, before Samantha Reynolds took a seat next to Nick. Her father, Ted Reynolds was a prominent businessman with family ties to the political world. Lucas observed slyly at her flirty banter with Nick.

"You look great, Nick," she smiled brightly.

"You too, Sam. It's been far too long," he replied with his own smile. "How was your summer?"

Between her touching his arm, the laughter and private jokes. Lucas smirked and took a drink from his glass, continuing to observe the two. A little later, she had been called away by her father to meet some people, where in which she kissed the blonde boy on the cheek and promised to be right back.

"Something happen I'm not aware of, Nicholas?" Lucas asked his friend, with a smirk playing on his face.

"She's just a friend," he answered, blushing a little.

"I'm sure that's all it is, if being a friend entitles the implication that she wants to get in your bed, which happens to be...there, I believe." Lucas pointed with his head, while, toying with his glass. It was time for a refill.

"We went out a couple of times," he admitted. "My dad's hoping her father will gun for him in the next election."

"And you've taken it upon yourself to ensure he gets another run at being mayor for another term," Lucas patted his friend on the back in mild approval. "Sly move, Archiabld. Though, I must admit, it's a bit translucent, wouldn't you say?"

"It's a nothing serious, I mean it's just been a few dinners and a drink or two. It's not like we've done anything…you know?"

"Anything interesting, yes Nicholas, I gathered," he grinned, signaling for a refill.

"K! You're back," Charlotte smiled broadly at the sight of her best friend. The two girls shared a hug, as they made their way to the table. "When did you get in?"

"Late last night," she replied. "I slept through most of the morning. I missed you, C," she replied. "I wish you'd have come with me to Paris. It was amazing."

"I'm starting to regret not going," Charlotte relented. "Sounds like it would've been more fun than hanging out with the Lord. And it certainly would have kept things interesting," a Bass smirk began to play on Charlotte's face.

"What are you talking about?"

"You haven't heard?"

"Heard what?"

"Gossip Girl claims you've taken a lover in Paris," Charlotte answered coolly. "Why didn't you tell me?"

"What?"

Charlotte wordlessly scrolled through a list of bookmarked Gossip Girl posts on her phone before finding the one she was looking for and reading it out.

"We hear K has spent the summer in Paris with a beautiful boy. Not that we blame her. Where better else to have a romantic rendezvous with a fairy tale over the summer, than in the city of love? But it looks like she's returned to the UES alone. Did things not end happily ever after, K?"

"Gossip Girl has it all wrong," Kayla replied, shaking her head. "I went on a few dates in Paris. You know, maybe lunch, walks along the Seine and some macaroons. I'd hardly call that taking a lover."

"Hmmm, for now," she mused and the two engaged in a few laughs on their way to their table.

Kayla Archibald and Charlotte Bass had a friendship, close enough to rival that of their mothers or their brothers. Like their brothers, they had been practically inseparable since they were little. Charlotte had taken over Constance as Queen, with her best friend at her side the whole time. They'd been there for each other through struggles and heartbreak and fun times.

Kayla was the daughter of Nate and Serena. She resembled Serena as much as Lucas resembled Chuck, with the exception of Nate's eyes and nose. She was beautiful, if not always the brightest, but Charlotte knew that her friend had a good heart and it was usually in the right place, usually. Kayla always shared a good relationship with her brother, Nick, but had always held a more distant one with her brother from her mother's first marriage, Oscar Humphrey.

The two passed him on their way to the table to join the others. Unlike most of the guest, Oscar chose to dress as minimally as possible. He wore a plain, button down pale blue shirt, with a grey sweater vest over the top and a red tie, much to his reluctance. Oscar didn't like ties, he found them too constricting.

"Hello, Oscar," Kayla greeted her brother out of politeness. "How was your summer?"

"Okay," he nodded, without much else to say. He wasn't a talker. But she was his sister, so he added. "Yours?"

"Good. Paris was wonderful."

"Yeah? So was Brooklyn."

Oscar Humphrey was Dan and Serena's son. His parents had gotten divorced when he was very young and he'd ended up spending half his time in Brooklyn and the other half on the UES with the Archibalds. Initially, he hadn't seemed to have a problem with it, until one day he became brooding and bitter. He'd started to think that it was Nate's fault his parents couldn't have a happy marriage. The sudden change into a brooding and bitter introvert had most of his friends at school ostracize him, which was fine with Oscar, because he preferred to read Fitzgerald and write by himself.

"Ah, he's emerged!" Milo dramatically stated as Henry made his way out of the bathroom.

Henry finally looked like himself, well more like himself. His hair was combed neatly and parted to its original style, with his wavy dark hair, just edging on his forehead. He was handsome and had the most mixed features from his parents. Blair's eyes, Chuck's hair, Blair's nose, Chuck's jaw, Blair's forehead, Chuck's lips. The list went on and it had always been a debate ever since he was little about who he resembled more. But he did look more handsome cleaned up and fresh, than he did ragged and drunk for days.

He was wearing a striped purple and white shirt, with the sleeves rolled up and black pants (casual wear in the world of Henry Bass) and his father's old signature scarf. He wore it when he felt…lost? Hurt? Anyway, whatever he was feeling now, he wore it as a source of comfort.

"You realize it's barely the end of summer?" Milo prodded, referring to the scarf.

"You realize I don't care," he grumbled.

He might have cleaned up, but he was still hungover.

"So," Milo took a seat on the chair opposite to Henry's and perched his feet up on the table. "What's the deal with you missing class and drinking and doing different women all day?" Henry shot him a half bemused, half quizzical look. "Not that I don't approve," Milo added. "Because that does sound like a lot of fun. But it's not very…Henry of you."

"I don't need your help, Milo," he scowled.

"I'm just looking out for your best interests, nephew," he drawled out. "Some girl breaks up with you and you turn into a Goddamn mess. That Hamilton girl must've been a firecracker in bed, huh?"

Henry almost spat back a remark to wipe the smug look off of Milo's face. But before he could, the older guy not handed him his phone that had just gone off.

"What is this?" he bit back a snarl.

"Just read, dear nephew."

Spotted: A, checking into the Ostroff Center. We thought her breakup with H was because of a busty burlesque dancer, but is there something more to it? Everyone knows Ostroff is only for the disturbed or the addicted. So what's A's big secret? I'll be sure to keep you posted.

AN: Hope you enjoyed that ,and please review to tell me what you think and if I should continue. Please go easy, it's my first fanfic.