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“I—I don’t know what to say—” Jess stammered into the phone. She wasn’t used to taking phone calls during work hours, and the back hallway toward the “secret” conference room on the C-suite floor didn’t seem private enough.
“Say you’ll come,” Aidan responded in a low voice. “It’s Bermuda. And it’s only for a weekend—I know this is so crazy. And so soon. But it’s your birthday—and I have the miles. It just makes sense. It’s a two-hour flight—”
“Well, I mean—” God, he had just been a random hookup in the bathroom at one of Greg’s house parties—but he was turning out to be the most impossibly nice person on the planet.
“Come on, Jess—it’ll be fun. It’s just a weekend.”
She sighed; she saw Karolina emerge from the secret conference room—a secret call, she supposed? “well, a weekend, I guess…”
“Yes, long weekend.”
“A long weekend…”
“You deserve it.”
He was right.
“I’m booking a flight tonight,” he finished. “Let me know by then, yeah?”
Jess relented and ended the call.
“I’m not one to eavesdrop,” Karolina reached out and squeezed Jess’ forearm, “but whatever the long weekend is—you should go.”
Jess didn’t say anything.
“You should go.” Karolina nodded once before leaving her alone.
After a moment of decision, Jess returned to her desk. She glanced over at Kendall, who was, oddly enough, in his own office rather than at the conference table in his father’s. He was on a call—with one DJ Squiggle—about his “surprise” for his father’s anniversary dinner in Dundee. She had been slated to go…but nothing had been confirmed yet. Jess sat down to a full calendar before her. She had ten minutes before she and Kendall had to jet off to a meeting on Pierce.
Tony sat next to her, reviewing Kendall’s talking points for the congressional hearing.
She eyed him carefully; Tony never got to go anywhere. Tony didn’t go to England. L.A. Argestes. He wasn’t slated to go to D.C.
Maybe it was Tony’s time to go somewhere. And Jess could skip off to the pink sand beaches of Bermuda for a long, much-needed weekend. With Aidan. Who had started off as that hook up, and it turned into drinks at Daisy’s Cocktail Garden, Peter Pan doughnuts on Saturdays--until he’d offered to take her on a trip. Interesting. Main character energy this morning.
A life? Outside of work? This was so insane.
Jess allowed herself to feel happy about it. But not relaxed.
“Hey, Tony,” she said—very off the cuff and not at all pre-rehearsed—”I—I may have a conflict for Dundee.”
He looked up from his document. “Oh?”
“Yeah—I—yeah, that weekend,” she said, “so—I was thinking—since Fiona is tied to the Pierce thing here—would you want to …go?”
Dundee was not exactly a destination. But Tony brightened. To travel? For work? On a jet? His passport was updated only last month. He couldn’t help but smile.
“Yeah—you need me to go?”
“Uh, I do—You have—”
“Yeah, I’ve got everything I need,” he said quickly, “yeah, I’m all set.”
Jess heaved a quiet sigh, heartened by his grin, “fantastic. OK, you can put yourself on the flight manifest, and I’ll transfer my hotel room to your name.”
“Yeah—um—does—Kendall know--?”
“No, I…” Jess glanced back at Kendall’s office. Ten minutes until the Pierce meeting. “I have to talk to him.”
Tony hesitated, looking at her, suddenly unsure. He nodded without saying another word and returned to his reading.
Jess rose from her chair and tiptoed over to Kendall’s office. He was finishing up his call.
He sat on the couch with one foot propped against the edge of the coffee table and spoke in a loud voice as she poked her head in.
“Yeah, dude,” he said, “I know you’re like the fucking best, like really fucking superior. Whatever you conjure is going to be fucking epic. I can’t wait to collab on this. I’ll see you tomorrow in the studio, man. Thanks.”
Kendall ended the call and glanced up.
“Hey Jess, what’s up?”
“Hey,” she clipped, “um—the Pierce meeting is in about ten but—”
“Oh yeah—great, thanks,” Kendall said as he scrolled through his phone for costume inspo. Needed to keep it simple—to the point.
“But I…”
“Hm?”
“I was going to put Tony on the lead for Dundee,” Jess burst forth with the words before she could stop herself.
Kendall blinked at her. “You’re not going to come?”
Jess had a sick feeling in her chest as she regarded him. Even though she knew it had been nonsensical, she was anticipating anger from him, not abject disappointment. This was somehow worse.
“Um—” she shook her head to compose her thoughts and started again: “Um—he’s all prepped, ready to go. Um—I—”
“But why--?” Kendall couldn’t help the tone, but the words seemed non-pathetic enough.
She hadn’t been there for the England trip the week before. Or Hungary. And now this?
“I—” Jess didn’t know what to say. Of course, HR would not require any explanation for anticipated time off. She’d not taken one day in the last six months. And no two consecutive days in the past year. She’d taken one day when she had the flu.
“Um—I’m—requesting some days that—conflict—”
These were not words Kendall wanted to hear. He needed her. To prop him up. To guide him. To keep him afloat, these days. The crushing sensation in his heart was much more bearable when she was there , sitting silently by him.
“Conflict—” Kendall enunciated the word but could not keep his voice from shaking.
“—with the event in Dundee.”
Kendall’s mouth gaped, “oh—oh.”
What could she possibly be doing? he thought. He couldn’t think of anything. His mind didn’t work.
“Um—” he sputtered out some sounds, “uh, but—so, Tony?”
Kendall seriously considered contesting Jess on this. To fight her, to get her to cancel whatever stupid fucking plans she’d somehow made that directly conflicted with a huge night for his father. But he relished being the cool boss too much.
He also didn’t want to make it obvious that he was desperate for Jess’ presence to make him seem normal.
Kendall nodded, resigned, at the idea of Tony being with him in Scotland. Tony being down the hall instead of Jess.
“Yeah—um, yeah,” he shrugged, unraveling just a bit, “I mean, 3 weeks of vacation a year—you should totally take the days.”
“…yeah?”
“Ha, fuck, yeah,” Kendall bit down on the inside of his lip a little as he huffed out a hollow laugh, “of course, Jess. You deserve it.”
Kendall glanced at her as she stood just inches from his door. Her eyes were bright, maybe a little disbelieving, but the upturned corners of her mouth made him melt.
For the next week and a half, Kendall and Jess worked alongside each other—seemingly normal. For Jess, anyway. She was handing off more travel plans to Tony by the day, checking and double checking that everything was ready to go.
When they were alone together, Kendall struggled with asking her outright what her plans actually were. She’d requested off that next Thursday and Friday. Two whole days—and then into the actual weekend—she’d be off the grid completely.
Would she be taking it easy at home? Secret spa weekend in the Hudson Valley? Girls’ trip to Miami Beach? Not knowing where she would be was beginning to a consume him a little. A girls’ trip seemed safe. A romantic weekend seemed harder to conceive.
But what am I doing? he demanded of himself while they reviewed the terms for the Pierce deal. She’s allowed to have a life—even if I don’t have one. This is a job to her. She’s allowed time off—even if she’s never taken it.
She’ll miss my performance, he realized.
Maybe that was more ideal? In case he’d make a fool of himself? (No, he’d practiced too much.)
But Jess already had seen him at some of his worst points—she’d been privy to a handful of glimpses into his shadow self, and she’d never, ever hinted at a smidge of judgment. And it actually made her the best assistant he’d ever had.
And as each day passed, Kendall’s curiosity grew more intense after having made up a thousand different scenarios about the whereabouts of the person he spent nearly all of his waking hours with.
But it was on Wednesday—the day before she was slated to have off and two days before the Dundee trip—that a carryon and travel tote appeared by her desk. The day had started as any other: she greeted him with a cup French drip coffee at the elevator bank, and they reviewed the day’s schedule as they walked to his office.
But just as he was about to go in, the offending luggage caught his eye.
“Oh—um, all set?” he asked, gesturing to her bags.
“Yeah, uh—flying out of Newark tonight, so I didn’t want to go back home to—”
“Right, yeah,” Kendall agreed with her like he flew commercial all the time, “that makes sense.”
There was a pause.
“Um, so anyway,” Jess looked back down at her iPad as she and Kendall dipped into his office, “after the hearing prep, you’ve got dinner with some shareholders—”
“Oh, fuck, that’s right,” Kendall pinched the top of the bridge of his nose as he realized he’d just be eating shit for his father for the rest of his life.
“But it’s a pretty quiet day, other than that.”
“Yeah.”
“Do you need—”
“No, no—I’m good.”
Jess nodded, and she left him alone with his thoughts—which was always the fucking worst.
At around six, Jess popped her head back into his office with a reminder that Fikret was downstairs, awaiting to whisk him away to a shareholder dinner. Kendall was slightly taken aback when Jess followed him to the elevator bank with her bags.
“What time is your flight?” he asked, trying with all of the fibers of his being to be casual.
“Eight-thirty.”
He blinked, “yeah—that rush hour traffic—”
“—brutal—” Jess’s tote slipped off her shoulder. Kendall caught it.
“Oh, I got it—You have a car waiting—?” he asked as he took the bag.
“Um…” Jess stepped onto the elevator, and Kendall followed her. The doors closed and soon they were descending swiftly down, down, down. His stomach dropped.
Jess didn’t finish her thought. And Kendall wondered why—but was never, ever going to ask.
They were silent until the lobby.
“Where are you going?” Kendall blurted out his innermost thoughts—well not quite innerMOST—before he even crossed the security desk.
“Bermuda.”
“Oh—wow—what parish?”
“I mean, I don’t know—”
“You…”
“It’s a surprise…?” Jess said, dreading that if she told him where she was staying that he’d make a big deal of it. A grand show. A display. A gesture. She just wanted a quiet birthday weekend.
“A surprise--?” Kendall repeated like a quizzical parrot of some sort. How could she not know--?
They got outside—and much to Jess’ distinct horror—Aidan was waiting by the car he’d called. Two worlds were about to collide in an intersectional supernova, and Jess was not at all prepared. Her eyes became saucers. In spite of her excitement for the first true vacation since the start of her tenure at Waystar Royco, she was immediately filled with extreme dread.
Jess watched, in terror, as she saw Aidan dip his hand into the backseat of the SUV and pull out an overflowing, blousy bouquet of pink peonies.
Kendall, meanwhile, who could not believe his eyes, was about to approach Aidan and say, “excuse me, man, do you know this woman?” The very idea was outrageous to him. Every other evening they’d either part at the front entrance or continue whatever meetings they were conducting in the back of his car as Fikret drove Kendall home. But Jess slowed her pace as she saw the flower delivery guy—and gave a smile.
So, who was this fucking guy?
But Kendall, against all of his erroneous instincts, stayed silent. And tried to keep his mouth from gaping as he watched the scene unfold before him, still gripping the carry-on, like some frozen voyeur.
Aidan held out the flowers to Jess and, with a sheepish laugh, declared, “Happy Birthday!”
Kendall paled at the words.
Those flowers look really fucking stupid. Fucking Seymour Krelborn over here.
Jess wanted to crawl under a large rock, but there were none to be found in the Financial District. She accepted the flowers with a self-conscious huff; the scent was heaven. Aidan leaned in, super chill, and kissed her on the lips easily. Her cheeks felt warm. This was nice. And weird. Ah, the beginning of a maybe relationship—in front of the guy she spent seventy hours a week with. Totally normal. Everything was fine.
Kendall couldn’t stop staring. The hurt ambushed him. He wasn’t proud of it. The one comfort he could cling to was now being taken--
“Ready to go?” Aidan asked her, taking her rolling suitcase in one hand before turning to Kendall to accept the carry-on, “oh, thanks, dude.”
Kendall blinked several times, “and you are--?”
Aidan loaded the bags into the back of the SUV without waiting for the driver (seemed he worked out a lot, Kendall surmised) and then came back around with his right hand extended.
“Oh, this is Aidan—” Jess sprung in.
“Aidan Blackstall,” he said with a friendly handshake.
Kendall nodded with a cool, dismissive air. This guy was what? 6’5”? Sickening. And devastatingly well-adjusted. Infuriating.
“Aidan, this is Kendall—” Jess tried.
“Kendall Roy.”
Aidan’s demeanor shifted and broke the handshake. “Oh—oh.” He looked at Jess, who was standing off to the side with a smile pressed to her face.
“It’s—it’s nice to meet you,” Aidan said with a genuine fucking grin. “I’ve heard—a lot about you.”
Kendall allowed an eyebrow raise as he tried to process what he was hearing.
“Ah, yeah,” he responded, “well, yeah…wish I could say the same.”
Jess’ eyes became saucers.
“Where are you staying—in Bermuda?” Kendall couldn’t help it now.
“Um—the Hamilton Princess—”
“Oh, sure, sure.”
“You—you’ve been?” Aidan asked, making nice conversation because he was a normal person. Jess’s heart broke a little at his earnestness. He was not of this world.
“Oh—no,” Kendall scoffed, “no, my family has a house in Southampton.”
Aidan nodded. Jess closed her eyes for a moment.
“Yeah—I mean,” Kendall shifted his weight as a gust of wind blew through the streets, creating a wind tunnel. “If I had known—you—” he glanced at Jess, who looked nauseous, “you were going—you could’ve stayed there. At the house. If I had known.”
There was a pause between the three of them.
“Well, next time,” Kendall finished.
Jess took a huge breath. “Next time.”
Kendall nodded at her, and she watched in real time as the momentary bravado drained from his face. Four days to him would seem like a lifetime.
“Great to meet you,” Aidan said, smiling, before he got into the backseat of the car. Jess hesitated as she assessed Kendall.
“I’ll—I’ll see you Monday,” he said in a soft voice, daring to glance at her in the eye.
“Yeah—and I’ll be—” she waved her phone at him.
He shook his head, pained, “no, no. You—turn off notifications—it’s…it’s your birthday.”
Kendall laughed a little, “happy birthday—I didn’t—I didn’t know.”
“Yeah—well, with everything that’s been—” Jess brushed it off like she hadn’t been working for him for four years. Like he’d noticed her birthday before.
“Uh-huh,” Kendall’s shoulders sank under the realization that not only was he not a cool boss and never would be a cool boss, but he was also a terrible one. And a terrible friend.
He grasped her hand, “Happy Birthday. Go to the caves—they’re—they’re amazing.”
She smiled, nodded.
Kendall watched as Jess got into the car next to her tall surprise maybe-boyfriend. The vehicle pulled out into traffic and disappeared down Broadway. He got out his phone.
“Hey, Tony—yeah—um—contact the Hamilton Princess—yeah, I’m gonna need champagne delivered to a room. And flowers. Nice flowers. Like, classy flowers. Not like, stupid fucking peonies or some shit.”