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Jess should’ve known that it would only be a matter of time. Her first six months at Waystar Royco went well. Really well—even though she’d been working seven days a week and pulling sixteen-hour days. So, with each passing day, a little niggling voice kept reminding her she hadn’t made a mistake. Jess tamped it down, ignoring it. The stakes were far too high. To work for Kendall Roy? To be making three times the amount of money she’d been making at Sotheby’s? To be paying off every loan she’d ever taken out? In full? To live without roommates? The thought to her was insane.
It was too perfect, but her body—and her mind—began to dull without rest. Chasing the idea of being the errorless assistant became intoxicating—and increasingly impossible as time wore on.
But the mistake. The first big mistake. It happened on a Tuesday afternoon in October. And Jess never saw it coming. She had been listening in on a call that Kendall was on about Waystar’s possible acquisition of a Taiwanese media conglomerate. The request for the meeting had been set for weeks. The idea of the acquisition was so important that Jess’ eyes hadn’t even thought to register any other meeting requests at the same time; Kendall had been talking about the meeting—his first solo venture—for months. He’d check with Jess every day for a week leading up to the meeting to ensure no one had canceled. She needed this to go off without a hitch.
So she was completely taken by horrific surprise when she saw Lucy dart across the C-Suite office and sidestep her desk, going straight into Kendall’s office. Jess’ eyes widened as she saw Kendall pop up out of his chair, hastily end the entire meeting, and follow Lucy back down to Logan’s office.
Jess could hear Logan bellowing soon after Kendall went in.
“…You took the meeting anyway?” Jess heard him yell.
There was a clamor of voices, but Jess couldn’t make out what everyone was saying. Logan’s voice cut through: “Well, get her in here!”
And with a bleak realization, she knew exactly who he meant.
Soon, Lucy appeared at Jess’ desk with a worried brow, grimacing with regret at being the bearer of the worst news. She didn’t say anything, but Jess knew to make her way to Logan’s office. She’d never spoken to him. And he had never even given a glance—let alone a word—to her. Her body felt numb as she entered the room, seeing Logan in the chair, Kendall off to the right, looking ashen, along with Gerri, Frank, and Karl on the sofas, waiting.
Logan was silent, flinty. Jess waited, feeling ill.
“There was a request sent this morning,” his voice was quiet, dark.
“Dad, Jess was only following my instructions—” Kendall tried, but Logan disregarded him.
“--for that meeting—the meeting that he was in—” Logan jabbed his finger toward his son “—to be postponed because the terms had not been finalized yet. And you didn’t see it?”
She hadn’t. She hadn’t noticed. A gross oversight. Gerri winced at what was coming next.
Jess shook her head, wordless. Kendall tried to protest again, but Logan pounded his fist on the desk once.
“Then open your fucking eyes,” Logan punctuated each word with a roar. “Now get out.”
Jess nodded and disappeared out the door. Logan turned to Kendall.
“And you,” he accused, “you should’ve known—”
“Dad, I—”
“OK, fuck off,” Logan waved his hand, “just—you’re off the deal. Frank will take lead.”
“But Dad—I have—”
“Five—I need five. Everyone out.”
Gerri, Frank, and Karl, careful and silent, filed out of Logan’s office. Kendall still stayed, trying to speak. His father rose out of his chair and went to the window. And Kendall knew what that meant; he’d been given the cold shoulder too many times not to know.
He stepped out quietly, immediately in search of Jess.
Meanwhile, in the bathroom by the elevator banks, Jess sat, sobbing noiselessly in a stall. Her vision was blurry, and her throat burned as she fought her body from devolving into complete weeping. Her first mistake was so much worse than she ever could have anticipated. Awful. Humiliating—and she’d let Kendall down.
Jess grabbed at the toilet paper to blow her nose. She sniffed a few times as she heard the door open. She grew silent and froze.
“Jess…?”
“Gerri…?”
Gerri stepped in and mused for a moment, making sure they were alone. “It’s a rite of passage, you know.”
“What…is?”
“Crying silent tears in this bathroom.”
The candor with which Gerri peppered her words brought Jess from the brink of despair.
“…Though I haven’t cried in this bathroom in over twenty years--well before this reno.”
“It—it was my fault—”
“Yes—you made a mistake,” Gerri shrugged, “but Logan can be—” she was careful “--Logan.”
“Yeah.”
“But I think,” Gerri sighed, “Kendall may be looking for you? He seems at sea—without you.”
“I don’t know about that.”
“No—actually,” Gerri pushed back even more candidly, “no, he’s—he’s been much more organized since you came on board. And that’s a major departure from his previous behavior.”
Gerri had wanted to tell Jess that he’d been much less of a shitshow since she’d been hired but held back the word choice. It was for another time.
Jess didn’t answer.
“Listen, I’ve got to get back—” Gerri sighed, stern, but her heart broke for the young woman inside the stall, “but I can get him for you—he should be the one to talk to you anyway.”
“No—no, you don’t have to—”
“Well, I think it’s best—”
Jess wasn’t about to argue about anything with Gerri. She heard the door open and then close once more, leaving her alone again. It was then that Jess burst into tears, thinking about the further humiliation; this was not some nightmare. This was real. Kendall was searching for her? She wanted to dissolve into the marble wall and never show her face again—especially not to him.
Meanwhile, Kendall was trying to keep his cool as he scampered about, looking for her. She wasn’t at her desk. And she wasn’t in his office. Her circled around the floor once, checking empty conference rooms, at a loss. He came across Gerri when he’d returned to his office. She was there, seemingly waiting for him.
“Looking for your right hand?” she asked with an arched brow.
“Yeah—she—”
“Follow me,” she said, and Kendall dutifully trailed her as she brought him to the hall that led to the women’s bathroom. “She’s inside.”
“Oh—um—” Kendall, immediately awkward, stepped back a little, “um—I—do you want me to—"
“Listen,” Gerri shrugged, “can I say that you should enter the women’s bathroom? No. But do you want to keep the best executive assistant you’ve ever had? Yes—I think you do. And I need to get back to Logan—so, it’s up to you.”
She shrugged again and gestured to the door before leaving him. Kendall stared at the bathroom sign, weighing whether or not to go in. He knew that he honestly couldn’t function for the rest of the day without her. For one, she had all of the access to his calendar—which he had completely forgotten.
Kendall placed his hands on the door and took them off—and then did the same again. Alejandro passed by, on his way to the men’s room, and Kendall tried to act casual.
“Hey, man,” Kendall muttered.
Alejandro nodded with a quizzical look before entering the men’s room.
Kendall cleared his throat and steeled his shoulders. “Hey—um, hey, Jess?”
No answer.
“Is—Is there anyone—can I—um—” Kendall cleared his throat again, “can I come in?”
“Yes,” came the muffled response from within.
And Kendall pushed the door open. He saw Jess’ feet in the second stall.
“Hey—um,” he paused, “actually—do you want to come out--? So I can…”
There was silence for a moment, but he heard Jess shift and then unlatch the door. She came out, biting her bottom lip to keep from exploding into tears, and he was immediately taken aback. He didn’t know what to say, and so they stood there for a moment, in front of each other, him by the sink and her by the stall. The bathroom door swung open, and Karolina stepped in, emitted a tiny gasp, and then immediately registered the situation.
“I’m—gonna—” she pointed to the exit and disappeared.
Kendall spurred into action and locked the door behind her. He glanced back at Jess, who had turned away from him. Her head was bowed. More humiliation. Couldn’t she have her first work breakdown in peace? Without anyone noticing? Even encased in the windowless marble bathroom, she could feel the office gossip topic switch towards her.
“Hey—” he said softly and stepped toward her. He saw that she held a mascara-smudged bit of toilet paper to her eyes. She was quivering. “You—you wanna come out of the bathroom?”
He needed prep for the next meeting—and had no idea when it was. But then he became aware: Jess’ shoulders were shaking. She was crying—or at least trying not to cry and doing a poor job of holding it in. Kendall blanched at the idea that his words just then had pushed her to tears. The last thing he wanted to do was to make her cry.
To be like his father.
“Hey—it’s OK—” Kendall reached out, placing his hand on her arm haltingly. He patted it, really not knowing what to do. Jess couldn’t hold back the tears any longer, and one soft sob escaped from her lips before she held her breath again. Kendall reeled back, panicked by her emotion.
“I’ll—I’ll understand if you want to fire me—” she whispered, turning slightly—daring to glance at him over her shoulder-- “It was such a stupid mistake—”
“Hey, hey—” Kendall couldn’t think of another word to say. He held out his hands to her, as if to stop her from crying. But in her despair, Jess mistook his arms out as an invitation for a hug. Her all-encompassing humiliation had rocketed her to another plane of existence—otherwise she would’ve realized hugging her boss in a locked bathroom would’ve been…weird.
“Um…” he mumbled, accepting her arms around him with an ease that shocked him, “I know—my dad—can be tough.”
An understatement.
“It’s—it’s only because he’s so passionate—” Kendall continued. He glanced at her face’s reflection in the mirror and gauged her reaction. His sentiments didn’t help, even though it happened to be the thing he’d told himself over the years: he’s so passionate, he can’t help it.
“I’m so sorry,” Kendall whispered, staring at her reflection. And he realized something grim: that by her very association with him, he’d subjected her to the same abuse he’d endured for years. He knew it wasn’t logical to blame himself, but he did. He held onto Jess, leaning his head against her hair and felt her lay her head on his shoulder in return. He vowed in that moment to protect her, to shield her—if she wanted to continue working for him, that is.
“I’m so sorry,” he said again. “But—heh—welcome to the club.” There was a pause.
“What?” Jess stepped back, searching his face for some explanation. Her eyes were red. Some eyeliner trailed down her cheek.
Kendall shrugged, wincing at his glib choice of words while he fought the urge to wipe the errant eyeliner stain away from her cheek, “well, I guess…I know how it feels when my dad—when my dad gets angry…I’ve known all of my life.” He laughed humorlessly.
Jess inhaled, watching him. Kendall’s face fell, and he stared at the bathroom counter. The designers had chosen marble, even though it stained. While he searched for words, he grabbed some paper towels and handed them to her. Jess accepted, grateful to toss the toilet paper in the trash.
“So, you’re not going to quit, right?” he asked, only half joking.
“You mean—you’re not going to fire me?” Jess’ brown eyes were wide, blinking, defeated, and Kendall’s heart broke at the site of them.
“Fire—fire you?” Kendall choked on the words, “no. No. Not at all.”
“But I—”
“Yeah, that’s—that’s nowhere near the worst mistake I’ve seen an EA do. Let alone me,” Kendall laughed, but he felt like crying along with her.
Jess smiled a little, covering her face with her hands, and Kendall felt encouraged. Why was she ending up making him feel better?
“If anything,” he huffed, “the only feedback I’d give you is that you’re just bad at making mistakes.”
Jess’ lips curled into a reluctant smile—and Kendall smiled right back. “Um, so, you’re fine. Well, you’re more than—but, no. I’m not firing you. I wouldn’t dream of it.”
She gazed at him as a wall broke down between them. He lifted the corner of his mouth in tender way, tipping his chin down as he looked at her.
“You good?” he asked her.
Jess nodded.
Someone pushed at the door.
“Oh, fuck,” Kendall glanced back, realizing he had locked himself in the C-Suite women’s bathroom with his assistant. “Uh—this—this is out of order!”
“What?” came the reply; it was Joan, Logan’s longtime secretary. She knew Kendall’s voice anywhere.
“Yeah—if, um, you could call maintenance?” Kendall called.
There was an awkward pause. Jess was afraid to laugh and clasped her hand to her mouth. After a moment, they heard Joan’s footsteps retreat from the door. Kendall took a breath.
“Um,” he rubbed his temple in thought, “maybe you need to check—if the coast is clear.”
Jess nodded, ready to conspire. She turned the deadbolt—which, oh my god, why was there a deadbolt on the bathroom door?—and poked her head out of the cracked door like a small animated mouse.
The coast was indeed clear; she didn’t see Roman emerge from the elevators—fresh off the plane from L.A.—so she could never have calculated a chance meeting. Her second major mistake of the day.
She stepped back in and gave him a nod. Kendall took the opportunity to stealthily slip back to his office and stepped out into the hallway; he had to admit it was kind of fun? To be sneaking around? With Jess at his side? He put the idea in his back pocket: nefarious, high stakes things with his trusty assistant at his side—could be useful.
Eager to get back to business, Jess allowed herself a quick glance in the mirror, wiped the eye make-up marks from her cheeks, and jumped out—maybe too soon—from the bathroom.
Kendall had encountered his brother at the end of the hall. They stood, chatting. Roman, not one to miss a beat, glanced past Kendall’s shoulder toward Jess. Roman watched her slide past and continue on toward her desk. Kendall quickly attempted to bring Roman’s attention back.
“So how’s that screenplay coming, bro?” Kendall’s attempt at small talk was hollow. Roman narrowed one eye as he put what he had seen together: he saw his brother emerge from the women’s bathroom, quickly followed by his new assistant…
Roman ignored the question: “A little bit of the ol’ afternoon delight?”
“Excuse me?”
“In my experience, these bathrooms are just impossible to have a good fuck in—” Roman was nonchalant, “but you found a good position?”
“What the fuck, Rome,” Kendall withered at the audacity of the question.
“Oh, no worries,” Roman hit Kendall’s chest with a limp punch, “every basic Yuppie always needs a midday refresh. Take the edge off. Glad you could fit one in—even if it is with someone who’s been here for five fucking minutes.”
“Yeah—it’s not—it’s not like that.”
“Oh?” Roman laid one finger against his cheek, in sarcastic thought, “no? So, it’s not fucking? It’s just some staid Victorian crush absolutely filled with self-flagellation and pining? Get the fuck out of here with that shit, Mr. Rochester.”
Roman left him before Kendall could come up with a retort. Kendall watched as his brother crossed through the C-Suite, toward his father’s office, and was hailed as a returning hero from the West Coast. And Kendall cursed him for being right.
He stood at a distance from the activity of the office and didn’t allow Roman’s caustic presence to ruin the moment he’d had with Jess; that type of moment, especially at the office, was entirely rare. He took a moment to savor its tenderness, however ephemeral and fragile it was, before returning to his desk. He threw a glance at Jess as she made up for lost time at her desk.
She could feel his eyes settle upon her, and she glanced up.
“You good?” he asked her—once more.
She nodded, offering up a small smile. “The Webex room is set up for your two o’clock.”
And she was back. The quiet, the closeness? Gone--completely replaced by a flawless veneer of professionalism. God, she was so good at it that it made Kendall realize just how upset she'd been. He wondered if they’d ever get another chance to recreate what had happened between them that day--because he was chasing that feeling.