A/N: Inspired by the trailer to finally get this out. Can't wait for the Jess/Kendall interactions! Thank you so much for your continued support of this story. So grateful for you folks readin' and reviewin'. In the meantime, I hope you all enjoy this meager NUGGET. Prepare yourselves for Cringe!Kendall.
Kendall had taken up smoking a few years before as a way to quell the drug urges. American Spirits were his go-to. Sure, it was what the insufferable Bushwick crowd smoked, he thought, but picking them up at the corner bodegas made him feel cool.
But he wasn't about to get backyard chickens anytime soon.
Smoking gave him an excuse for breaks during the day. Breaks from the meetings, Roman's Cheshire Cat nonsense posturing, the specter of his father's bad business dealings from the '80s that led to the billion-dollar debt he was now saddled with, Jess' glances constantly asking him "are you OK?"
If Kendall had stopped to articulate it, he would have realized that Jess had seemed to be silently surveying him now, assessing him—definitely more than usual. He was now on a mission to prove to her—and everyone else—that he could handle the insurmountable task before him. Kendall could not, by any means, look weak.
He reached out to Rava. He started texting her more in between the drop offs and pick ups, for secret advice, for encouragement, for propping up.
Jess took silent note of it all and brushed it off. They weren't together. They weren't involved. He had a private life—and wouldn't it be better for everyone if she and Kendall stayed far away from each other? Would Rava be Jess' first choice for Kendall? No, not at all. But Jess knew better to stay silent.
She was getting good at that. Less talking, more notetaking.
"Are you sure you don't want to come to L.A. with me?" Kendall asked the day before he left for a two-day trip to the West Coast office.
"I thought you wanted me to stay here and work on the new Vaulter angle—and the RECNY Ball—Connor is asking—"
"Yeah, yeah," he quickly said, "but you could…"
Kendall trailed off, scrambling for words.
"I think it's best if I'm locked in here," Jess returned.
"Of course," he paused for a moment, "shit, the RECNY – that's next week, yeah?"
Jess nodded and slipped out of his office. Kendall squeezed his eyes shut for a moment, cursing at himself. He'd gotten off cocaine. And had gotten on to Jess.
A week later, Kendall had slept with Rava and only felt worse about himself. He raced around the executive floor to a meeting with Jess at his heels, feeling giddy that she was close and that she kept in step with him, perfectly in sync. They were deep in conversation about scheduling.
"Oh and—for the RECNY—" Kendall added, "Rava's being—she's busy."
"Uh huh," Jess replied, busy tapping an email on her phone.
"So…" Kendall trailed off, realizing he should've rehearsed this somehow. "I…"
"Oh, I meant to remind you—I'm sending you the reminder in writing now," she hit the button and the message jetted off with a "whoosh." "That night, Thursday, I can be on-call, but I requested off."
"Wait—you—"
"Yeah, I sent the request to you two months ago—"
"Wait—why—"
"Um."
"Sorry, I—"
"It's Lance's birthday," Jess said, "and a group of us are going out."
"Oh, of course," Kendall, through every fault of his own, felt a shot of panic course through him when he realized Jess wouldn't be with him for the RECNY Ball. Even on the perimeter of the room, tablet in hand. In stilettos, eating a salad standing up. The image of her in that black dress flashed through his mind as quickly as he pushed it away. He recovered and tried to grab on to any semblance of coolness he had left, which, at this point, were ragged remnants. Plan B.
"Hey, listen," he said, "could you just reach out real quick to Anna Newman's people? Ask them if she's available Thursday?"
"Oh—um, yes. Of course."
"Yeah, I mean," Kendall said with a hitch in his voice as he slipped into the conference room, "I'm so busy these days, and she's probably … it's just easier to go through people."
"Of course," she responded quickly.
Kendall didn't mean to hurt Jess in that moment, but it was plainly displayed on her face. He had been extremely careful to not treat her as "his people" but now, in this moment, she was vividly reminded that she was an employee. Like a sting that wouldn't go away. A sting that threatened to infect the healthy tissue surrounding it.
But the hurt he'd caused seemed to relieve the pressure building inside of him.
Kendall had saved the company from a billion-dollar disaster—just in time for his father to not retire and to plant a fertile seed of doubt in Kendall's mind about his ability to lead. The RECNY Ball, at Connor's helm this year, had been something of a modest success and re-established the street cred stability of the company. Set the industry buzz in a positive direction, for some. Stewy was wary, watching.
On the ride home, he was feeling reckless. Just a few years ago, he'd hit up his network for some "goodies," as he used to call it. But not now. He scrolled through his contacts.
"Hey—Kerry?"
"Kendall—what's—" the surprised voice came through. He would call Jess, but…
"Hey—I know," goddamnit, why was he so creepy? The rich loser looking to party with the cool kids—that feeling of worthlessness came right back to him from boarding school. "…so—you're out for Lance's birthday, right?"
"…Yes."
"Cool, cool," Kendall replied, trying to sound only a little bit interested, "where—um, where you guys at? I'll come buy everyone a round."
"Um, Please Don't Tell."
"Haha—well, I um, I won't—" Kendall emitted a weird laugh that he hadn't planned on anyone else hearing. He could somehow hear Kerry suppress a wince on the other end of the line.
"No—that's the place," Kerry's face contorted to keep from laughing into the phone. Jess watched her from across the table. What the fuck was about to happen?
"It's called Please Don't Tell," she finished.
"Oh—right, I mean, of course," he said, feeling his age. And his position. And his sobriety. "Yeah, um, be there in a bit."
"Wait—he's coming?" Lance asked as Kerry set down her phone in disbelief.
"Apparently?"
"Why?" Tony scoffed, "I mean—isn't it…weird?"
"Hey, if he wants to buy drinks, maybe we should head to a more expensive place?" Fiona quipped, "we could hit up the The Rose…"
"Or maybe he could get us to jump the line at Death & Co?" Tony said.
"Jess," Lance said, jolting her out of her apparent daze, "where do you think we should go?"
"I think—I think we could still go to Crocodile Lounge—"
"What? Come on! No! He's going to be paying for everything—"
"Yeah, but he doesn't," she began and then restarted, "Kendall—he doesn't need to be in a bar. I can get him to leave when he comes—"
"And miss out on free drinks?" Fiona cackled, "never. This is gonna be fantastic."
"This is gonna be weird," Jess felt slightly ill. Maybe it was the mezcal, maybe it was the sinking realization that their special private dynamic she'd kept hidden for three years would be exposed under dim lights and alcohol.
"Oh my god, Jess, relax," Tony reached out and squeezed her hand.
"Yeah, it's completely normal for our boss to crash this friendly gathering," Lance smirked, "and ply us with $20 drinks."
Jess heaved a heavy, silent sigh and watched as Kendall came through the door, putting on his faux confident strut, and sidled up to their booth.
"Happy Birthday, man," he extended his hand to Lance. His employee accepted it with a bemused, if accepting, smile.
"Thanks!"
"What are we drinking?"
Fiona was on it: "Benton's Old Fashions for Kerry and Tony, Cascade for me, Paddington for the birthday boy and a Green Light for our girl Jess."
Jess looked at her work wife and cocked her head to the side with a piercing, but fleeting, glare.
Kendall, not one to ever wait for table service, relayed the message to the under-amused bartender, who quickly changed his countenance when Kendall threw a Franklin into the tip jar and five more onto the rubber service mat.
"Their whole tab—on me," he said before giving the bar counter a little tap. "And I'll just have a bitters and soda."
He turned back to the table, swallowed hard, and slid back into the booth, next to Jess, who had to move in slightly to accommodate him.
"Look at this place," Kendall surveyed the room, "cheugy, am I right?"
Lance's eyes widened for a split second before he righted himself. With a downturned smile, Kerry nodded in silent amused agreement.
Jess crunched on a few leftover ice cubes in her glass.
After half of an awkward pause, the novelty of the boss being at the bar with them wore off and the others defaulted into a conversation while Jess was forced into small talk with Kendall, who seemed close.
"How did the RECNY go?" She stabbed the dying ice with a compostable straw.
How did it go? Kendall asked himself. He didn't know.
"Great," he replied. "All the WASPs were guilted into forking over their fortunes. All's well that ends well." He cleared his throat.
"And how was Anna?" The words left Jess' lips quietly before she had the chance to stop them.
Kendall thought of the interaction he had with Eva after Anna had left. He was still reeling from it, which was probably why he ended up next to Jess in a bar.
"Great," he repeated robotically, grateful to receive the drink from the server. "Green Light, eh? What's in it?"
"Not sure," Jess muttered after a sip; should she tell her sober boss—whose sobriety was directly connected to her livelihood and her conscience—the ingredients of the alcoholic drink she was currently imbibing?
"Hey, so it's an executive assistant huddle, I see," Kendall said.
"Yeah, we've grown incestuously close since we spend a hundred hours a week with each other," Fiona edged in, surveying Jess' seeming shift in character. "We spend holidays together, too. Friendsgiving next week!"
"Hey, now," Kendall smiled weakly, "you all, I know, put in the time. We don't say thank you enough around the office—so, uh, cheers."
He lifted his glass and so did the others; the assistants exchanged furtive glances with each other as they drank, each planning to probe one another with questions later regarding Kendall's presence. What, exactly, did he want from them?
Again, the group conversationally left Kendall and Jess to speak to one another. Jess could feel her face getting hot. He was even closer.
"Hey," he said in a low voice, "I just wanted to also say thank you to…you."
Jess' heartrate quickened, and she found herself sucking down her drink. Was there about to be a train wreck that she couldn't pull away from? Those things tended to follow Kendall around.
"You know, you've…" Kendall ran his thumbs across the cut diamond pattern in his glass, "gone above and beyond, especially with all the long hours recently—Vaulter, my father—hey actually, speaking of my dad—"
Jess' radar began to ping. Never once—ever—ever, did Kendall speak of his father without a specific project context, and even then, it was brief. Clipped. Terse. Resentful.
Jess was reminded of the time Kendall threw his phone and it ricocheted off the car partition into her knee. She recalled the melting ice-
"—Does he seem different—to you?"
"Different? How?"
"Uh, you know," Kendall chose his words with precision, or at least, he thought so, "you know…different. Like, not himself."
Jess kept her face void of emotion, but her eyes widened a little. She took another sip of her drink. "I don't know. I don't know him well enough to say. Maybe…ask Frank? Colin…?"
"Of course—of course," Kendall responded quickly, "of course. He's still recovering—I mean, he just needs time. We'll see."
Jess paused, feeling mischievous but keeping her voice low. She spoke into his ear, and Tony glanced at them once.
"Why do you ask?" She asked quietly, the strap of her silk top threatening to slip down her shoulder. "What are you planning?"
Kendall shrugged with a sigh. "No, just wondering."
Jess nodded and knew Kendall was in planning mode. She'd seen it time and time again, usually when he struggled to say something to her, something regarding their angsty, complex dynamic. But now? Now it had a different context. She couldn't quite figure it out, but given how fragile he seemed to be, how small, Jess knew it wouldn't be a good thing.
"Hey, folks," he downed his soda and slid the glass to the center of the table away from him, "I gotta jet."
Jet? What is this, 2003?
"But all drinks on me. All settled—enjoy your evening. Happy Birthday, Lance!" He rose from the booth, realized he had no close friends in his life, and gave a wave goodbye.
Once Kendall was gone, Lance rubbed his face in amazement, "I mean, honestly, I'd hatewatch that whole interaction over again."
"Oh, come on," Fiona said, "we got free drinks! Kendall's not bad—"
"Yeah," Lance agreed, "he's not, but, so awkward? I mean, I know there's a board meeting coming up, and he gets antsy with those but… What even—"
"Shh. Don't question. Just drink. Then we can go to Crocodile Lounge and get pizza," Kerry said, "whatever Kendall wants will be dealt with by Jess tomorrow at 8 a.m. As usual."
"I'm gonna run to the restroom," Jess got up and disappeared out the door. Only Tony raised an eyebrow as she went.
Jess made it out to the street in time to catch Kendall, who was still waiting for his car to pull around.
"Hey," he straightened, surprised to see her. The tight jeans, the silk tank, that lipstick—
"What's up?" she asked, searching his face.
Kendall gulped and hoped she didn't notice. He then realized she meant "why did you come?"
He waited for a moment, to see if she would fill the space.
"Listen, uh," Kendall laughed bitterly, "Anna Newman's seeing someone—and tonight was—it was, yeah, so—um—Eva's assistant might be sending an email or something or Eva—I don't know, look out for that. She told Anna to—nevermind. It's not important. I mean, if you get something from HR… Just—uh. Tonight was a lot. With my dad and everything—"
"Of course."
Kendall sighed, afraid to look Jess directly in the eye; she knew exactly what happened with Logan in Kendall's office. He settled on her collarbone and bit his lip.
"Um—walk with me," Kendall motioned to her.
"Uh—" Jess hugged herself against the late November air. He responded by shedding his overcoat and draping it across her shoulders.
"Come on, it's important," he said.
Jess' knees felt like they would give way, but she complied.
"It's like 35 degrees—you don't have a coat?"
She smiled with a streak of judgment, "not when I'm going out."
He smiled to himself.
"So…" Kendall started uncertainly, and she held her breath to see where he would go with this, "there's a board meeting coming up."
"Yes…"
"And—and I want you to," Kendall stuttered, "I want you to be saved from whatever shitstorm might come of it."
Jess' racing heart seemed to freeze inside of her ribcage. "OK…"
"Moving forward," he continued, forging ahead to turn onto Avenue A, "I might not be able to tell you everything—if only to shield you."
Jess didn't say anything.
"But I need to know if—"
"I'm with you."
Kendall stopped walking and turned to her. "Yeah?"
She pulled his coat tightly around herself and said her words in a low, easy voice: "Of course. We watch out for each other."
He wanted to scoop her up into his arms and devour her. But, tonight at least, he was not that guy.