A/N: ...Hello? I know, its been forever and I haven't updated. I'm so sorry for making you guys wait. School is my priority and over the past few months, my workload was incessantly relentless. I apologize for my tardiness of this update and hope there still may be a few readers around the world who are still interested in this story. Without further ado, here is the next chapter- minus the VDB mealtime. It'll be in the next chapter, but I decided to end the chapter before it.

Note: Anything italized is a reference to a flashback.

Disclaimer: I do not own Gossip Girl or any of its characters. Just the OC's I've created.

Chapter 9: Chuck in Real Life

The week was uneventful and flew by in a flash. It was afterschool on a Friday, and Evelyn was found in her room. Papers were strewn all over her desk, her new math textbook cracked open. Hunched over her desk, Evelyn punched equations into her calculator, and scribbled her answers in her notebook. Her ear buds dangled from her ears. She was so engrossed in her work she didn't hear the forceful pounding on her door.

Chuck opened the door and sauntered in. He tapped his sister on the shoulder to get her attention. She jumped, surprised. "Oh my god! Don't sneak up on me like that!" She breathed out evenly.

Chuck smirked at her. "My apologies…" His eyebrows knitted together. "What are you doing?"

"Homework," Evelyn shrugged her slim shoulders.

"On a Friday afternoon?"

"Well yes. Everything I learned today is still fresh in my mind-and I'm a day behind in math already, which is never good this early on. Why are you looking at me like that?"

Chuck's lips parted and he returned," I think you're the only person that actually does their homework around here. Except the Humphreys of course, but they're both on scholarship." Chuck sunk down onto her plush bed.

"You know there is a study that shows that when people study and complete their homework, their marks are significantly higher. Crazy I know but you should try it." Evelyn smirked.

"That's too much unneccessary work."

"You don't try at all in school?" Evelyn asked skeptically.

"Well I do try when I sit in the classroom, however I don't exactly take initiative outside the classroom."

Evelyn crossed her arms. "Um, so how do you expect to be accepted to college?"

Chuck smirked and rubbed his two fingers together. "Oh," Evelyn replied. "Isn't the saying money talks, bullshit walks?"

"Precisely. The Ivy Leagues will take any of us because we have money and will invest it in the University."

"But that's so not fair for those that actually try and don't have money!" Evelyn protested.

"I didn't say it was fair, but that's the way it is."

Evelyn turned away. Did they really have it that easy? They probably try to buy their teachers out to give them good marks, Evelyn pondered. It wouldn't be all that surprising. If its one thing Evelyn has learned so far is that cash will solve anything.

"Now for the reason for my intrusion." Chuck stood from her bed and hovered behind his sister. "We're going out tonight."

"We?" Evelyn asked bemused.

"No, your maid and I," Chuck replied sarcastically.

"What are we going to do?"

"Well I think it's best for you to experience what I like to do, and next week we'll experience what you like to do. How does that sound?"

Evelyn smiled. "That's a good idea. I'm in."

Chuck genuinely smiled back. "Good. Now, first, we need to get you new clothes because those simply won't do," His eyes scanned her whole outfit; jeans, a thick sweater and Nike sneakers.

"My outfit isn't that bad," Evelyn replied defensively. She could tell by the wrinkled look of his nose that it was that bad.

"But isn't great either now is it?"

Evelyn sighed. "What's wrong with being comfortable?"

"Nothing- it's just with Gossip Girl around you'll need to look presentable," Chuck explained.

Chuck glanced at his watch. "We don't have that much time. Let's go."

"Where are we going exactly?" Evelyn tossed her pencil on her desk, and stood.

Already, Chuck was walking briskly out in the hallway. "You'll see."

Saks. That was his big surprise. On Fifth Avenue. In Manhattan. It was just like in the movies but it was real. Evelyn was experiencing a girl's dream. Well, a girly girl's dream to be exact.

Her brother led her into the store, holding open the glass doors for her to pass through. A lady greeted Evelyn upon arrival but brushed her off as soon as her brother entered the room.

"Hello Mr. Bass! So good to see you again! Can I be of any assistance?"

Evelyn just started between her brother and the saleswoman. They are on a last name basis? "Thank you Trudy but that won't be necessary. I've already called Marsha, who should be here at any time. We'll just be browsing thank you."

Her brother charged forward and Evelyn scampered behind. Her eyes darted around to the colourful racks of dresses, purses and shoes. The store seemed palatial compared to any typical mall retail store.

Evelyn caught up to her brother. "Are you a regular here or something? Because it seems like these clothes aren't your type."

Chuck smirked. "I've been here plenty of times before to help a friend with some advice."

"And now you're going to help me?" Evelyn asked, her arms crossed, a smirk mirroring her brothers.

"Well someone has to."

Evelyn's eyes widened, "Oh, I see how it is. I'm now a pathetic charity case?"

Chuck rolled his eyes, "That's not what I meant."

Evelyn's frown turned into a grin, "I know, I'm just messing with you. Now what is it that I should be wearing? You're the supposed expert after all."

"Well, the truth is that I'm having my personal shopper come in to help you. Wait- there she is."

Evelyn turned to see a petite girl approach them. Her hair was chopped off, to look edgy and the short and straight ebony locks suited her face. She looked to be in her late twenties, early thirties.

"Hello Chuck."

"Marsha, this is Evelyn, Evelyn this is Marsha," Chuck introduced. Marsha held out her hand and gave a firm handshake to Evelyn.

"It's nice to meet you," Evelyn said politely.

"Same to you," She then turned to Chuck, "So what's the event?"

"We're just going out tonight. It's not a black and tie event but not casual."

"Like a nightclub?" Marsha raised her eyebrow.

Chuck smirked. "Not exactly Marsha, but you know it wouldn't be my first time."

Evelyn watched as Marsha tilted her head back and laughed. "You're telling me! Evelyn I remember this kid when he was younger and would go out all the time!" She put her hands on her hips. "I'll pick out a few dresses to start, so just head on over to the dressing room okay?"

Marsha scanned over Evelyn's body, deep in thought. "I'll bring a couple of sizes but I can usually tell by looking at anyone. So, head on over to the change rooms and I'll be there in a couple of minutes.

"Okay," Evelyn nodded. Chuck led her past the racks of clothes and all the way to the back of the store. After they passed each rack, Evelyn gradually felt more self-conscious. Every other customer in the store appeared to have all the latest designer clothes. Yet, here she was in a thick sweater and sneakers. Sneakers!

An impeccably dressed saleslady led her into a dressing room. Evelyn waited outside for Marsha. "Is this really necessary? I mean look at this place!"

Chuck smirked. "Please tell me you've heard of Saks. If you haven't I will disown you."

Evelyn rolled her eyes. "Of course I know what Saks is, I'm just saying the excess of everything… it's just so much. I feel like-like a hobo in here!"

"I'm glad you finally realize this," he chuckled.


Marsha walked towards them hurriedly interrupting Evelyn's rebuttal. In her arms, she carried four colorful dresses. "Try these on first. We'll see if it's the right size and I'll bring more out."

Evelyn took the hangers and closed the door behind her. She assessed the dresses, one turquoise, purple, and a couple black. She stared for a brief moment and decided to try on the turquoise first. Better to get the worst one out of the way.

Carefully, Evelyn stripped out of her jeans and into the silky dress. It came to her mid-thigh, and cinched at her waist. The dress covered her shoulders and had a v-neckline. The right shoulder had an odd bow pattern, which matched the same color of the dress.

Evelyn assessed herself in the mirror. It wasn't bad, she supposed. She removed her hair-tie from her hair, letting her chestnut waves frame her face.

She opened the door, her face full of question. "So?"

Marsha's eyes were focused. "The sizing is right. The color hmmm… something about the color."

Evelyn looked at her brother. He was perched on a cushioned stool, her legs and arms crossed. "It doesn't match her eyes. Her eyes are far bluer."

Evelyn nodded. "I'll try on the next one." She didn't bother giving her input since it clearly didn't have any worth.

Evelyn then slipped on a swing style dress. It had a white collar, with a couple buttons running down her chest. It cinched at her waist, and flowed outward from her narrow frame. She gingerly stepped outside her dressing room.

The look on her brother's face said it all. "You look like a pilgrim."

Evelyn surveyed her form in a full length mirror outside her dressing room. She stepped forward toward the three panels and grimaced. "Whoever designed this dress should be fired."

She shut her dressing room door, and repapered with a different dress. This dress had long sleeves, and was the length of a sweater dress. Every inch of the material sparkled with bedazzled jewels.

She opened the door and stepped out. "Please tell me this is as hideous as the last."

Chuck studied her. "It's worse. If only we had spotlights you'd be a disco ball- except not as round."

Evelyn rolled her eyes. "Thanks."

She tried to glare at him but found him smirking at her. Evelyn didn't know what she found more puzzling. Either her wearing a ten thousand dollar designer dress that her aunt and uncle would never purchase, or her brother giving her better fashion advice than their personal shopper. There must be something wrong with this city.

After trying on five other dresses, Evelyn wanted to just go back to her room. She'd rather study than try on these repulsive, ridiculous and overpriced dresses.

Just when she was about to give up, she reappeared in front of her brother.

"How about this one?"

Evelyn turned to face the mirror, and looked at herself. She quirked her head sideways, assessing the look. Her body was draped with a mixed color of iris and indigo. It clung to her left shoulder, with a large shoulder sleeve, and came to knees.

Evelyn turned to her brother. "So?" She prodded.

His usual smirk flitted into a side grin. "It's perfect."

Spotted: Chuck Bass escorting our newbie E into the Oak Room. Did the first date go so well that C wanted more? Has our devil really turned into a prince overnight? Keep on the lookout kiddies… Our very own Queen B would like to know.

"You still haven't told me where we're going," Evelyn resisted the urge to pull down her dress as far as it could go. She didn't need to worry since her dress was in no harm of showing her skin, but she couldn't help being uncomfortable in it.

"Well I should first have a disclaimer. What we're about to do is not exactly legal."

Evelyn's blue eyes widened. "What?"

He's a lunatic, she decided. She was related to a mad-man in a dapper suit. How very inconspicuous of him.

"There's no need to panic. It isn't that big of a deal really. We do it here all the time. I have since I was thirteen."

His pride was evident in his voice. Her brother's hazel eyes glistened, as he reminisced of a memory rolling around in his head.

He's still crazy, Evelyn thought. Some big brother Chuck was. Weren't older brothers supposed to protect their siblings? Not endanger them?

The limo rolled to a stop. Evelyn tried to gather her wits, trying to protect herself from whatever awaited her outside the limo. What could her brother possibly be interested in that was illegal? Poker? Vandalism? A gang?

Wait, Evelyn paused. Her brother couldn't possibly be in a gang. No gang member would ever wear that much purple. Ever.

Chuck opened to door as Evelyn slid across the buttery black backseat of the limo. She followed behind him and immediately saw a bright sign. It illuminated the words "The Oak Room."

Evelyn looked at her brother questioningly. "What's the Oak Room?"

Chuck didn't answer but walked determinedly to the door. He held the door open for Evelyn allowing her first glance. It was a poorly lit room with dark oak panels-hence the name. She followed Chuck past a grand ballroom area and into a bar. Dozens of people casually mingled and supported crystal glasses in their hands. Chuck sat on one of the pea green bar stools.

"A bar? That's the surprise?" Evelyn plopped on the stool beside him.

"Don't sound so excited about it," Chuck smirked.

"Well, when you mentioned what we were going to do wasn't legal," Evelyn lowered her voice to a whisper, "I naturally thought of more dangerous possibilities."

"Is this too tame for you?" Her brother smirked.

Evelyn rolled her eyes, "No! I just thought it would be something else! You didn't exactly elaborate now did you?"

Chuck glanced past her briefly. "All in a good surprise right?"

"That's true, but I'm not one that likes surprises I guess," Evelyn shrugged.

"Dually noted," Chuck nodded. "So, what's your drink of choice?"

"Well I haven't exactly tried everything, but now that you're introducing me to the good stuff…"

"Cheap beer didn't suffice before?"

Evelyn cringed. "I've never liked beer. Every time I smell it I think of…" Evelyn stopped herself. She began to play with the locket around her neck and bit her lip, as the memory surfaced.

"Let's go talk in here," He suggested. He pointed inside another room. A bedroom.

Evelyn backed away, knowing his true intentions. Why couldn't he just leave her alone? She barely knew this guy. "No thanks, I have to go find Katie she's been looking for me."

She tried to turn away but felt a claw clamp around her arm. The claw pulled her toward him sharply, just like a predator snatching its prey.

"What are you doing? Let go of me!" Evelyn tried to fight back.

He pulled her chin close to her. He breathed heavily like a beast did in storybooks, and the smell of beer polluted her face. The stench came closer and closer as she tried to break away violently.

"You're so hot," he mumbled before he went in for the kill. He lowered his beer tasting lips on hers.

"Think of what?" Chuck asked snapping Evelyn's attention back to the present.

Evelyn averted her eyes to the oak floors. "Oh, just some party last year. They had keggers," Evelyn explained evasively.

The bartender approached and addressed Chuck.

"Mr. Bass what can I get for you?"

"I'll have a scotch on the rocks." He turned toward Evelyn, "Would you like something to drink?"

She brought her blue eyes back up to the bartender briefly forgetting the memory. She panicked briefly, wondering if someone would know their underage. She turned to her brother who waited patiently and said, "I'll have a cosmopolitan martini please."

"On the rocks or straight up ma' am?"

What did that mean exactly? Evelyn wondered. She didn't want to appear underage; it would be a dead giveaway. She turned to her brother and gave him a pleading look.

"She'll have it on the rocks," He answered for her.

The bartender nodded and disappeared.

"Cosmopolitan?" Chuck asked.

"Yes, is that a problem?"

"No, it's just a girl drink that's all. Have you ever tried it before?"

"Nope. I saw it on Sex and the City once and it looked really good," Evelyn shrugged.

"You like Sex and the City and now you're in the city? Now I understand everything," Chuck teased.

"I don't like it! My friend Katie was obsessed with it and made me watch an episode! You know that's not the reason for-well- you know…"

"I'm just teasing sis."

Evelyn felt her phone vibrate on the counter. She checked it and read the message. Gossip Girl was at it again.

Spotted: C and E having a cozy drink at the Oak Room. Is it just coincidence that Queen B just happens to be celebrating H's birthday at the same place? I don't think so. Who knows what drama is brewing. Keep me updated kiddies, this one is worth watching.

"Blair is here?" Evelyn looked up from her phone.

The bartender brought their requested drinks. Chuck swirled his scotch. "I know."

"You did? How?" Evelyn scanned the room without success.

Chuck set his drink down on the napkin not looking up. "It's because she's sitting behind you, in the corner, with a group of girls."

Evelyn swiveled on her stool and sure enough Blair Waldorf was glaring at her. It wasn't the first time this has happened. What are the chances they'd meet up at the same bar?

"What is up with her?" Evelyn faced her brother questioning.

"What do you mean?"

"Ever since the first time she spoke to me it feels like she has something pent up against me. She doesn't even know me."

Chuck starred past her, at Blair's table. "She's threatened."

Evelyn didn't believe him. "What? Why would she be?"

He continued to stare at her and didn't respond immediately. Evelyn waved her hand in front of her brother's face. "Hello?"

"Don't worry about her. Just stay away from her and you'll be fine. I'll make sure of it."

"That's what everyone keeps telling me, I just wonder what it means. She told me to stay away from you."

Chuck's attention snapped right back to her, a small hopeful smile on his face. "She did?"

Evelyn sighed. "Um yes, but I don't know why. Wait, are you…did you…" Evelyn stopped as she came to a realization. Was her brother dating Blair Waldorf? Did Blair think she was stealing her brother away from her?

"Have you dated Blair?"

Chuck took a sip of his drink. "No, we're friends."

Evelyn rolled her eyes. "Sure Chuck, I'll believe that as much as you saying you don't like purple. If you're trying to convince me of that, you are a terrible liar."

Chuck remained unmoved. "Well, it's true."

Evelyn crossed her arms. "Guys and girls can't be friends, end of story."

Chuck smirked. "You got that from When Harry met Sally didn't you?"

"Yes, but I could have told you that before I saw the movie. Guys will only be friends with girls they think are not attractive, and you have been staring at Ms. Waldorf ever since we've got here."

Chuck glared. He was annoyed that she was beginning to be able to read him so easily. Most people couldn't or didn't bother. "Since when are you the relationship expert?"

Evelyn turned rigid. "I'm not… I've just… seen this situation before."

Evelyn sipped her drink. To her surprise, it was refreshingly tasty.

"I'm sorry to interrupt but I just wanted to say hello." Evelyn swiveled to face Blair's smiling face.

"Hello Blair," Evelyn smiled back and addressed her minions curtly.

The notion of staying away from Blair wasn't working. Blair seemed to find her whenever she had something to say. But Evelyn didn't want to give Blair the satisfaction. Evelyn sat up and continued to smile innocently.

"I see you didn't follow my advice. Shame. I was only trying to help you." Blair fluttered her long eyelashes innocently.

Sure you were, Evelyn thought. You seem like the caring type.

Chuck put down his drink. "Why would she listen to your advice Blair when she has mine?"

Evelyn's eyes widened. She was about to open her mouth when Blair interrupted.

"Girls, why don't you go on ahead, I need a private word with Chuck." Blair's smile had evaporated into a menacing scowl. The girls were hesitant, not wanting to miss Blair's counter, but walked away slowly. Blair stepped closer to Chuck, completely ignoring Evelyn intentionally, but still wanted her to hear every word.

"Waldorf, what brings you here?" Chuck asked innocently.

"Don't play innocent Bass it's never worked on you. I've been celebrating Hazel's birthday like a mature adult, something you are not," Blair said pointing at Chuck's chest. Chuck looked unabashed by her insult and allowed Blair to continue, "I know the game you're playing Bass and it isn't fooling me. You knew I was going to be here and just because you dangled some random girl in front of me doesn't make me jealous like your deluded mind thinks I'm feeling. I know how I'm feeling thank you-"


Evelyn watched defenseless. There was something going on between the two but Chuck wasn't saying anything. Why was he so adamant on denying it? Why was Blair talking about jealousy if they were only just "friends"? Something was going on.

"You always did like them young and stupid. Too bad for you I'm not like that-"Blair began to wobble on her heels.

"But Blair listen, you've had too much to drink-"Chuck tried to take Blair's hand, attempting to keep her balance. Blair pulled it back hurriedly.

"Let go of me Bass!" Blair pushed his arms away and stumbled into Evelyn. Evelyn pushed Blair off of her, glowering.

Blair briefly grimaced before turning her attention back to Chuck. "Why don't you take you're little girlfriend back to her place, fuck her and leave like you do to everyone else!"

She turned on her heels and stomped out. Chuck called after her again but didn't chase after her. Instead he sunk back into his stool, crushed. "Sorry about that." He drained his glass and waved the bartender back for a second.

Evelyn's head was spinning. What just happened? First Blair was attacking her, and then Chuck and Chuck didn't even do anything. Was he using her? What was going on between Chuck and Blair?

"What the hell was that?" Evelyn hissed.

"It's just Blair, she needs some time to cool off."

Evelyn felt her patience waning. "No it wasn't. She implied some cruel things about me and you didn't even stand up for me."

"She wouldn't hear any of it Evelyn. She was way too drunk."

"That doesn't matter," Evelyn paused, thinking, "You didn't just want to spend time together tonight did you? You used me to do whatever it was you needed to hurt this Blair person."

"Just stop. You don't know what you're talking about," Chuck replied.

"Yes I do. Look, I don't know how you treat people here, but the way I've been raised, I'm not taking that shit."

"Whatever Blair's problem is has nothing to do with you."

"Oh really? Then why am I a pawn in an absurd chess game you two seem to be playing? That involves me." Evelyn stood up. "I'm going back to the penthouse. I'm using the limo and you can find your way home."

Chuck sighed exasperated. "Evelyn, this is all just a misunderstanding."

"A misunderstanding? Well whenever I ask for answers you never give them to me. So when you decide to straighten it out, let me know and explain it to me."

Evelyn picked up her purse and stormed out of the bar and angrily huffed at Arthur to go back to the penthouse.

What did all of this mean? Here Evelyn believed that her brother was looking out for her, like any sibling would- but he was using her for something that made no sense. Whoever Blair was to Chuck, she seemed to have a lot of power over him and his decisions. It wasn't just that, Blair had power everywhere. No matter how nice Evelyn can try to be to her, Evelyn has learned that Blair will never leave her alone. Thanks to her brother.

When did everything get so complicated?

Spotted: C alone and abandoned by B and E after a heated argument. Why the long face C? You've must've known B would strike back eventually.

You know you love me,

XOXO Gossip Girl

A.N: Alas, she was bound to see scheming Chuck in action at some point! Could you imagine how confusing it would be to witness a Chuck/Blair mindgame and be in the middle of it? I'd be just as confused. As for the flashback, there will be plenty more in the upcoming chapters to piece E's story together. So right now, nothing is as it seems.

Anyway, if you have any thoughts, or comments, I'd love to hear a response if any readers are out there. Please review!