Chapter Five
Based off They Shoot Humphreys, Don't They (3x09) with many original scenes and alterations
X
Walking down the streets of Manhattan was always an adventure for Jenny. Especially in the mornings. The hustle and bustle of the city while manic certainly kept things alive. It was almost magical, in the sense that the city never slept. It was constantly moving.
The October air was unusually chilly as she huddled closer to her father, thankful for his warm body heat. They were meeting Dan for breakfast in a fancy new diner that had just opened. It was long overdue for a Humphrey family breakfast. Ever since Dan had started NYU, they hadn't seen much of him as he was often too busy, so it was a perfect opportunity to catch up and try new food.
"So, a cotillion, huh?" Rufus asked, tucking his hands into his coat pocket as they headed down the street. She recognised the gesture as one he often did whenever he was embarrassed to talk about something he considered quite girly. A vivid image of the talk flashed in her mind - when she was around twelve and her mother had left, Jenny had started her period for the first time and with no one else to turn to but her father, it had made for a very uncomfortable discussion between the pair.
Jenny smiled fondly as she shook away the memory. "Uh - yeah. All the other girls at Constance are taking part, so it should be fun."
"Right." Rufus nodded, though the concern was visible on his face. Jenny could tell that he wasn't a fan of the idea, but wasn't likely to voice his opinion aloud. If there was one thing she loved about her father, it was his constant showal of support for his children, even if he didn't necessarily agree with their decisions (the only exception being if he thought they went too far - like Jenny often did last year).
"So, um, who's your date?" he asked, scratching the back of his head awkwardly as they entered the diner. Jenny spotted her brother who sat alone, at the far left table near the window, waving them over.
"Escort," she corrected as they edged closer to Dan, "and I don't have one yet."
As they took their seats, Dan leaned forward in interest and asked, "Who doesn't have what yet?"
"Your sister needs an escort for the cotillion Lily's hosting," Rufus answered, picking up a menu and focusing his attention onto the breakfast items.
"Cotillion?" Dan repeated. "I didn't know you were going to take part in that, Jen."
"I wasn't planning too," Jenny admitted, lowering her voice so that only her brother would hear her, "but as queen of Constance, I need to take part, otherwise it's considered as a sign of weakness."
Dan rolled his eyes the same way he always did whenever Constance was mentioned. He claimed it reminded him of his time at St. Jude's and all the surrounding drama, which he didn't miss in the slightest. "Well, we both know you never back down from a challenge. Why don't you take Eric? I'm sure he's an expert when it comes to these kinds of things."
"I wish. But apparently, since we're now related, he's exempt from having to escort me."
Dan wore a frown. "What a bummer."
"You know," Rufus said, placing his menu back onto the table, "that you don't have to go through with the cotillion if you don't want to. Just because you want the other girls to respect you doesn't mean you have to follow their expectations." It was clear that despite their soft murmuring, Rufus had still managed to pick up on his children's discussion.
"It doesn't work like that, Dad. This isn't Brooklyn - it's the Upper East Side. If you miss out an event like this, you become an instant social pariah," Jenny said with a sigh. No matter how many times she had explained it to him, he never seemed to understand. Much like Dan, her father would fail to see past the superficial layer of glam, couture and quadrilles, and into the bigger picture. She supposed it was a guy thing, they were never much for gossip, and was probably why she found it easier to talk to Lily about certain situations than her own father.
"Well, I'll love you no matter what your social standing is," he said, giving her an affectionate pat on the head.
She batted his hand away and smoothed down her bleached blonde hair. "Thanks, Dad, but I'm pretty sure that it's an unwritten rule to love your child no matter what."
"She got you there." Dan chuckled at his father.
Rufus muttered something under his breath before standing up. Though she didn't catch every word, Jenny was sure she heard him mention something about raising know-it-alls and had to refrain herself from giggling.
"I'll go order. I know you both well enough to know what you want to eat," he said, collecting the menus from the table and striding over to the counter.
As he left, Jenny took the opportunity to stare at her brother, analysing him with both interest and scepticism. He was in an unusually good mood since they had entered the diner and she wondered why that was. Dan was reading something off his phone, a really cheesy grin plastered on his face, and suddenly she realised what the cause of his euphoria was.
Propping both her elbows up on the table and resting her chin on her hands, she gazed up at him with a knowing look. "I take it things with Olivia are going well?" she asked.
"More than well, it's going amazing," he said, still grinning. "I think I've finally found my dream girl."
Resisting the urge to sigh, she instead flashed him a patient smile. In Jenny's opinion, Dan always thought he found his dream girl - no matter who he was dating, they had always seemed perfect to him until the honeymoon phase finally wore off and the facade faded. Take Serena, for instance. When they had first dated, Dan would often mention how he had lucked out with a girl like her, perfect in every way, shape and form, that was until she was thrust back into the spotlight and the glare of which had almost blinded him. It was a very messy break up, and since then he had sworn off dating celebrities. But then Olivia came along and the rest was history (though in her opinion, she didn't think that would last long, either).
As much as Jenny loved her brother, even she had to admit that his taste in woman was questionable at best.
She opened her mouth to change the subject but was stopped short at the arrival of two unwanted guests. Even the grin on Dan's face faltered by their presence.
"Humphrey. Little Humphrey," Blair Waldorf greeted in her typical offhand manner. Next to her, Chuck gave them a single nod of acknowledgement.
Jenny spotted her father still at the counter, in what appeared to be a deep conversation with the owner of the establishment. She quickly turned to Dan, the two exchanging knowing looks before he finally spoke up.
"Blair. Chuck. What a pleasure. Is there anything we can do for the two of you?" he asked, his words coated with a glaring layer of sarcasm.
Blair seemed to have picked up on his tone and smirked. Behind her, Chuck appeared bored as he scrolled through his phone. "Nothing from you, Humphrey. I came over here to speak to Little J, actually. I heard she'll be taking part in the cotillion this year and wanted to wish her luck."
Jenny quirked a brow, wondering what exactly the brunette had wanted from her. "I'm right here," she drawled, "no need to talk about me in third person. And yes, I am taking part in the cotillion this year."
"Well, that's a given," Blair said haughtily. "Every queen takes part."
"Can you make this fast, Blair?" Chuck interjected impatiently, "I have a meeting to attend."
His girlfriend ignored him, placing her hands on her hips as she continued, "Word on the street is that you're still looking for an escort."
"So what if I am?" Jenny huffed, irritated by her incessant theatrics. Blair always liked to make a spectacle of others and wherever she went, she attracted an audience. Today was no exception, the other patrons of the diner were staring in their direction, Rufus included.
"Blair." Chuck sighed, placing an arm on his girlfriend's shoulder, but she shrugged it off.
"Nothing, except it makes the queen look weak," Blair continued in an even tone. "And we can't have that, now can we, Little J?"
"Look, Blair. Just lay off her, okay? We're here to eat breakfast and mind our own business. Take your theatrics someplace else," Dan cut in, folding his arms as he glared at the couple.
Though she was grateful that Dan was defending her, Jenny wanted him to back off. She hated appearing weak and needing her big brother's help, especially against Blair. She may have loathed the older girl, but somewhere deep down, she still yearned for her respect.
"What do you have in mind?" Jenny asked, meeting her eyes carefully. She could have sworn she saw Blair's eyes soften a smidge before they went hard again. But then again, it was so fast that she may have imagined it.
"Well," Blair began, "we can discuss it at the gathering Lily's hosting tonight. I have plenty of ideas to go about, and as your mentor, I can assure you that this will be a cotillion you'll never forget."
With a scowl, Jenny peered down at her phone as she read the incriminating blast Gossip Girl had just sent out: Gossip Girl here. Just like the mob, New York prep schools have their own five families. You may be the John Gotti of Constance, Little J, but that doesn't mean you'll ever be part of this Costra Nostra.
She clenched her fists. Oh, when she got her hands on whoever wrote this -
"Oh, my God! Everyone's here. Come on, let's go and say hi," Sawyer exclaimed, snapping Jenny out of her musings as she and the other minions rushed to go greet the other queens.
Taking a deep breath to soothe her aching nerves, she was quick to slip on a mask of indifference as she watched the scene unfold right in front of her. Each queen glared at her with vehemence, as if she were the gum on the bottom of their cherished Louboutins, and Jenny tried frightfully hard not to squirm under their heavy gazes. Suddenly, she came to an epiphany - she was in way over her head. Being the queen of Constance was one thing, but to compete with the queens of other prep schools was a whole other territory that she wasn't familiar with in the slightest.
She hated to admit it, but maybe she needed Blair's help, after all.
Clad in an gray wrap dress, Blair looked the definition of poise and elegance. It was almost effortless for her. Jenny watched the brunette carefully as she gazed around the room, her eyes scanned over the other participants in a calculating manner.
A waiter approached them, offering a selection of canopies but was immediately dismissed by a bark from Blair. The former queen bee then turned to Jenny and said, "I'm glad you came to your senses."
Jenny rolled her eyes and was about to answer but was interrupted by her step-sister.
"Blair," Serena said coldly. "There's a list of debs and their mentors on the coffee table. You're more than welcome to have a look at who you've been assigned to. My debs right here, right Jenny," she added, wrapping an arm around Jenny's shoulder.
"Uh…" Jenny trailed off, blinking in confusion. She could have sworn Blair was her mentor as the older girl had told her earlier, but then again she had yet to check the list. Maybe Blair had lied.
"No she's not," Blair protested, "she's my mentee. I specifically put in a request with Lily and she assured me that I'd get Jenny."
"Not according to the list you didn't."
"The list be damned!"
Serena sighed and asked, "Blair, are we really doing this right now?"
"I gave you a chance to apologise," Blair responded, folding her arms across her chest.
Ah, Jenny thought, now it all made sense. Blair and Serena were clearly in another cold war and wanted to drag her into the middle of it. No wonder Blair had been extra eager to take her on as a mentee, even feigning concern for Jenny's escort problem, but of course the older brunette had an ulterior motive. After all, no one acted out of kindness or sincerity in the Upper East Side, a lesson she really should have learned by now.
"How about you apologise?" Serena continued.
Blair scoffed in indignation and said, "I'm here, aren't I?"
Having finally heard enough of their dramatics, Jenny cut in with an impatient remark, "Okay, look. I have enough of my own problems, so I'm not gonna let you guys make me a pawn in your war."
"War? What?" Blair had the gall to look sheepish at the suggestion. "Of course not."
Serena, however, rolled her eyes and grabbed her purse. "You know what, Blair, you can have her. I've got better things to do, like help Congressman Tripp Vanderbilt with his work. Unlike you, I don't need this. These are the last people in New York who still think you matter."
Blair's face fell for a second, as if Serena had slapped her senseless, but was quick to throw back on her mask of indifference. "Well, then go. Jenny's better off with me, anyway!"
Ignoring her, Serena gave Jenny a smile. "Good luck, J. You got this," she said before finally exiting the penthouse.
Muttering a quick 'thanks', Jenny turned back to Blair, who studied her closely. After a while of uncomfortable scrutiny, Blair grabbed Jenny's hand and yanked her further into the room, no doubt to instill some 'helpful tips' into her young and naive mind. Along the way, she grabbed some champagne. A night with Blair was guaranteed to be a long one.
"First things first, Little J. We'll need to sort out your escort dilemma," Blair said, pacing around the empty corner of the room she had dragged them into.
Eric, who had joined them not too long ago, added his input, "I can scroll through Facebook, if you'd like? There's plenty of young, hot guys on there."
"It's a start," Blair said in approval. "Good thinking, E."
Jenny sighed. "I just don't get why I can't go with Jonathan," she asked. "I mean, I know he's Eric's boyfriend and all, but he'd still make a great escort. Not to mention I'd have so much fun with him."
"She's got a point. He is a Whitney," Eric agreed.
"Ew." Blair frowned as if the idea was too much for her to stomach. "Definitely a massive no-no. Going with your step-brother's boyfriend? That's entirely out of the question." She continued pacing in deep thought, her hands glued to her hips.
"It's better than no escort right?"
She must have said the wrong thing for Blair's frown turned deeper in disgust. She inched closer to Jenny until they were almost nose-to-nose. Jenny tried not to show how intimidated she was feeling that very moment as she swallowed hard.
"Jenny, when you descend those stairs tomorrow night, everyone there will judge you based on that moment for the rest of your life," Blair said harshly. "This is not like your wedding day. Cotillion only happens once. Now, you already have a strike against you because of the whole Brooklyn misfortune. Don't let them pile up."
Pinching the bridge of her nose to refrain herself, Jenny let Blair's dig about Brooklyn slide. Now was not the time nor place to start an argument, especially in front of the other debs. "Okay, point taken," she said, exhaling loudly. "But I don't know who I could possibly find in such short notice."
"Perhaps I can help with that," came a nasally voice. Jenny, Blair and Eric had all turned to the direction of which it came from only to find a short, frumpy-looking girl standing there timidly.
"And who are you?" Blair asked in her typical inquisitive tone.
The girl fidgeted with her dress before she spoke up," Hi. I'm Kira. I go to Constance with you," she said, staring directly at Jenny.
She did look vaguely familiar now that Jenny considered it. "Yeah, sure. I've seen you around."
"You have? That's awesome," Kira gushed, almost star-struck, and Jenny already felt the second-hand embarrassment emanating.
Growing impatient with the small talk, Blair cut in. "That's great and all, really, but how can you help us?" she asked Kira.
Kira smiled shyly and said, "Well, Jenny could go with Graham Collins of course!"
"Graham Collins?" Jenny repeated incredulously, " As in the Graham Collins?"
From beside her, she heard Blair ask Eric who Graham was to which he answered, "Only like the hottest guy on the Upper East Side. He's sort of like our version of Nate."
"Yeah," Kira said eagerly. "Graham lives in my building. We've been neighbours forever. I can ask him for you, if you want."
"I know Graham, too," Eric admitted. "We went to Camp Suisse together. I totally forgot about him, Jen, otherwise I would have suggested him, too."
Trying not to squeal from excitement, Jenny played it cool with a nod. "That's totally fine. I don't mind going with Graham. If you could just send me his number, Kira, I'll text him myself."
"Great. Now that it's all settled, I'll take my leave," Blair said, with her usual resting-Blair face. She leaned in for a hug and muttered lowly so that only Jenny could hear her, "Word of advice, Little J. Get through the night, and the crown remains yours. If you mess up, I'll replace you with someone I see fit."
"Oh, don't worry, I won't," Jenny said, with newfound determination, hugging the brunette back. If there was one thing she never did, it was backing down from a challenge.
Jenny stood nervously in front of the mirror, trying her hardest to remain calm and compose her nerves. With all the other girls out of the dressing room, she was alone to have her last minute breakdown. She held onto the dressing table as she breathed in and out, just as her mother had taught her after her first encounter with stage-fright back in elementary school.
"Jenny?" Eric's voice rang out from outside the room. "Is everything okay?"
"Yeah - Yeah. I'm fine. Just a little nervous," she said.
The dressing room door opened and Eric came barrelling in. With one look at his step-sister, he immediately knew what was going through her mind. He grabbed her hand and helped her settle into one of the armchairs.
"Hey, Jenny, what's wrong?" he asked softly.
"I - I'm scared," she admitted truthfully. "Remember what Blair said yesterday? That after today, there's no going back. Only forward. And I just feel like I'm leaving a part of myself behind. It's like saying goodbye to Jenny from Brooklyn and hello to a society that I don't even feel welcome in."
Knotting his hands in hers, Eric gave it a squeeze and said, "Jenny, you know that's not true. Just because you're integrating yourself into high society doesn't mean you'll forget yourself. Think about all that happened last year - sure you went off the rails for a while, but you found yourself in the end, right."
He noticed the unshed tears in her eyes and continued, "Besides, not everyone is like Blair. Sure there are many classist snobs out there. But not everyone will look down on you just because of where you come from. In fact, some people may even root for you more because of it. Take the girls at Constance, for instance. They may not have liked or wanted you as queen at first, but eventually you won their respect, regardless of your background or status. If you can win them over, you can win anyone over."
With a deep, shaky breath, Jenny threw her arms around her step-brother and buried her face in his chest. "Thank you, Eric," she said, her voice muffled. "You always know what to say to make me feel better."
Eric chuckled. "It's a gift. Now come on, there's a crowd out there waiting for their queen to arrive."
"Hey, have you seen Graham anywhere?" Jenny asked her minions, who all shook their heads instantly. "Great. I'll just have to go find him before they start calling out our names. I'll see you all later."
With that, she made her way around the building, searching each room and coming up empty. At one point she bumped into Nate, who steadied her after she had almost lost her balance. He looked dapper in his black suit and bow tie and Jenny tried her hardest not to let that affect her.
"Hey, Jenny. You look nice. Have you seen Blair?"
"No. Not yet, fortunately. I'm looking for my escort, Graham Collins. He's, uh, sort of this year's, I guess, you."
The dimples on Nate's face stood out as he grinned in amusement. "I'll take that as a compliment," he said in good nature. "But, hey, have fun tonight."
"Thanks," Jenny said, tilting her head as she smiled at him. "I plan to."
After a while of searching, Jenny had almost given up when the organiser of the cotillion had asked all the participants to join them at the stage. Instead of following her fellow contestants, however, she continued prowling about the ballroom. Graham had to be in there somewhere. She certainly wasn't going to the stage without an escort and embarrass herself in front of the entire Upper East Side. If she wanted to continue her reign as queen and break the social hierarchy at Constance, she had to get through the night and defy Blair's expectations.
Finally, she spotted Graham's shaggy brown hair sticking out of a darkened corner. She quickened her pace, intending to drag him out of there until she spotted who he was with. Particularly, whose mouth he had his tongue shoved down. Jonathan's.
For a second, she almost didn't believe what she was seeing. How could Jonathan, one of her best friends and boyfriend to her step-brother be playing tonsil hockey with Graham Collins? She squeezed her eyes shut and upon opening it again, found that Jonathan really was making out with Graham. Her eyes worked perfectly fine.
Eventually, the confusion faded and rage took its place. She was going to expose the duo, not only to Eric, but to the entire ballroom. She took a leaf out of Blair's handbook and made her way toward the lighting crew, with a request that was about to shake the entire evening.
"Miss Kira Abernathy, escorted by Mr. Eric Van Der Woodsen." Kira walked over to Eric, who clutched her arms and led her down the steps. Next, was Jenny's turn, which she was anxious to get over with.
"Miss Jennifer Tallulah Humphrey, escorted by Mr. Graham Collins," said the announcer. As anticipated, Graham was predictably absent from the stage, and Jenny had yet to move an inch from her position.
She noticed the confused looks on people's face, particularly from her father and Lily, but their questions were answered by a single spotlight beam which focused onto the hidden corner where Graham and Jonathan were making out. The crowd gasped at the sight, and the boys quickly jumped apart when they realised what had happened. Though she was delighted that her plan had worked, Jenny still felt a shred of remorse for doing that to Jonathan. But then again, he had just cheated on her best friend, and hell hath no fury like a woman scorned.
Squinting her eyes, she searched for Eric and found him close to tears, the very same way he had found her earlier on in the dressing room. She hurried forward, needing to catch up with him. She needed to comfort him and make him feel better about the entire ordeal. It wasn't his fault he was the victim.
"Eric!" she exclaimed, running after him in her heels. It was harder than it looked. "Eric! Please slow down."
Eventually he came to a halt and she took the opportunity to run up to him. "Eric, I'm so sorry about what happened."
This time the tears had let loose, and dripped down his face like an overflowing fountain.
"Did you know, Jenny?"
"No - not until tonight," she placed a comforting hand around his waist and pulled him closer, until he was fully engulfed in her arms. He sobbed on her dress and she let him, uncaring that it would get wet. "I was just as surprised as you are."
Just as she said that, he froze. "Wait, did you know about it before this all happened?"
"Uh, yeah. I was the one who orchestrated the spotlight."
Eric tore away from her arms as if she had just burnt him. She tried not to look hurt as he took several steps back. "Why on earth would you do that?"
She sighed, running her hand through her hair. "I don't know. I guess I was just angry at him for doing that to you, and my inner mean girl came out."
"No, don't try and use me as an excuse to justify your behaviour," he said, his voice no longer shaky and growing stronger with each word. He lifted a hand and wiped away all trace of tears, though his eyes remained red and puffy. "We both know why you did it. You didn't want Graham Collins embarrassing you like that. He was your escort. You couldn't afford any slip ups that could cost you your crown."
"No, Eric. Please, it's not like that," she started, but he was having none of it. He threw her the dirtiest look he could muster and stormed away with nary a backward glance. Jenny stood frozen on the spot, feeling utterly helpless. She may have just lost her best friend.
Jenny Humphrey went to a ball. Jenny Humphrey had a great fall. And none of her minions, mentors or friends want to put Jenny together again. XOXO - Gossip Girl
As she read the latest gossip girl blast, Jenny decided that she had finally had enough. She would walk down the steps with the hottest escort, prove herself to the entire Upper East Side and Blair, and get her best friend back. Eric was right about what he said earlier - she wasn't going to lose herself. Instead, she'd get back up and try again. It was time to fix everything.
Phone in hand, she dialled the one person she considered her knight in shining armour.
"Hi. Are you still here?"
"May I have your attention please?" the announcer addressed the audience into the microphone. "Due to extenuating circumstances, we still have one last debutante to present. Miss Jennifer Tallulah Humphrey, escorted by Mr. Nathaniel Archibald."
The crowd gasped in astonishment. The faces of Jenny's fellow peers ranged from utter bewilderment to downright awe. Jenny tried not to smirk as she walked over to Nate. He offered her his arm and she grabbed it gratefully. The two posed for pictures with smiles and for once, she felt the approving gazes from the other queens.
Even Blair congratulated her, a genuine smile on her face as she did so. With this surge of a power move, she had finally won their respects. She had won the crown. It was over.
So why did she feel so empty?
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Ooo drama! I quite liked Blair in this chapter. Any thoughts?
