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Late Nights with Jack Sinclair

Summary:

Jack Sinclair is an enigmatic talk-show host with a dark secret: he has a deranged split personality, one that he isn’t fully aware of himself. When a new intern begins to work at his studio, her presence irreversibly awakens the dormant part of him that sleeps deep inside his psyche. Assigning her to be his personal assistant only makes matters worse, and as she struggles to ply herself out of his web, his obsession with her begins to form cracks in the public-facing, charming facade holding his career and life together.

Notes:

This story was vaguely inspired by a super young 1993 Conan O'Brien. Back then he was still green and in my opinion gave off a slightly more unhinged, erratic energy.

Pair that with my love for passionate dark romance (and I mean REALLY dark, with irredeemable, horrible men as the male leads) and here we are! This is also my first shot at writing something long-form, so please be gentle! :)

(See the end of the work for more notes.)

Chapter Text

Jack Sinclair is a household name for a reason. His voice—steady and smooth—drips with charisma and effortlessly commands any room he’s in. Even right now—the hum of the lights, the distant buzz of the crew members as they busily communicate through their headsets, and the occasional muted laughter dissipating from the live audience—all of it falls completely to the wayside in the wake of Jack’s fast-paced banter. Exceptionally tall and lithe though he is, his presence somehow fills every corner of the studio.

Primrose Lee stands off to the side, clutching her clipboard tighter to her chest as she watches the magic unfold with wonder. She’s recently become just another cog in the grand machinery of this show—unseen, unheard, and left behind the scenes. Still, as she watches him from this new angle she’s now privy to—as opposed to what everyone else sees from up on the screens or in the seats below—she feels a deep sense of gratitude. After all, despite her position as an unpaid intern, she gets to be far closer to his magnitude than she ever thought possible before.

Up-close like this, she isn’t left disappointed: he’s exactly the same as he was when he first sprang onto the scene back in her freshman year of high school. With his fiery locks swiped back into his signature slicked style—he is the absolute picture of youthful ambition. Though it’s hard to remember a time before his current status as universally adored—she recalls the very brief moment of skepticism that hung like a question when his first episode aired, long before he’d proven himself a worthy contender for the role. As the youngest man to ever take up the mantle of this coveted position as host—especially coming in on the heels of one of the oldest, longest-running, and most beloved predecessors—he had big shoes to fill. But back then, just like right now, he’d easily won everyone over with his conventionally good looks and unconventionally unique sense of humour. 

The live broadcast is now in full swing, and Jack is smiling knowingly at his guest—the washed up movie star John Daniels—who is rattling on about an anecdote that has nothing to do with the action film he’s supposed to be promoting. Every time Jack laughs, it fills the air with rapport, and every time Jack interjects or interrupts his guest, he successfully veers a lifeless story back into the land of engagement. Every word Jack speaks is deliberate, always serving as a punchline to a carefully crafted joke. Right now, he is gently poking fun at himself in a way that only those who are truly cemented in their own skin can, and the audience is eating it all up. They always do. 

Primrose can’t help but feel starstruck by him. She’s seen almost every episode that he’s been on, and being here—being a part of it now—makes her feel like some small, girlish dream of hers has been realized. She watches Jack’s every move, every twitch of his lips when the cameras pan his way, every movement of his eyes as he shifts his attention between his guest and the audience. He’s always performing, always controlling the pacing and tone of his show, but there’s also something else that’s there too—something she can’t quite put her finger on yet.

As a fan, Primrose has heard all of the rumours: the long nights of overworking his staff, the womanizing ways, and the utter ruthlessness behind his scorching success. At best, she thinks most of it is just tabloid drivel, and at worst, the kind of gross over-exaggerations that follow most celebrities of his ilk. But regardless, even though she knows it should bother her more, it simply doesn’t. She wants to be here, wants to be in his outer orbit, just close enough to watch him work and to hopefully absorb some of the confidence that radiates off him like a forcefield, but also just far away enough that she can keep herself safe from the harsh brutalities that make up the bulk of show-biz.

Without realizing it, as Jack begins to gesture animatedly with his hands, launching into his own relevant anecdote, Primrose finds herself leaning forward in oblivious rapture. She wonders how he’s able to stare so intensely at the audience without ever flinching under the harsh glare of the bright studio lights. He flashes an easy smile—the kind of smile that could instantly sell anything he wants— and then she observes how—just as seamlessly— he transitions the conversation back to the publicity circuit surrounding his guest’s latest project. He gives a wink and a nod, and on his cue, the obligatory clip from the movie begins to project behind them. He’s only a handful of years older than her, but the way he carries himself—like he owns the whole world—makes it seem like he’s been doing this for decades, even though it’s scarcely been even half of one. 

As the movie’s advertisement starts to wind down, Jack briefly turns away from his guest to face the general direction of the production crew, out in the wings. His vivid green eyes, so disarmingly alert, swiftly sweeps over the area. There, among her fellow peers and higher-ups, Primrose stands politely out of the way of the others. 

Suddenly, time seems to still, and Prim’s breath catches in her throat as a singular realization dawns on her.

He’s…staring at her.

Not only did he somehow spot her through the crowd and the dim lighting— but he’s set his gaze upon her with such an uncharacteristic solemness that she feels her palms start to sweat under the force of it’s tension. Primrose pries her eyes away from him for the first time since the director called action, pretending to look down to check her notes, and trying her best to ignore the distracting quickening of her heartbeat as it drums a bit too loudly in her ears. 

When she glances back up, he’s already moved on, back to his guest, and back to his larger-than-life, cheerful persona.

It was so brief—too brief— that by the time she fully registers what happened, she’s already doubting herself, and feeling a little silly, even, for the thought of it. 

He was just looking into the distance. Grow up, Prim, why would he be looking at you?

Jack’s voice cuts through her frazzled thoughts.

“And that, my friends, is why I’m not allowed in a zoo after hours!” he jokes, easing the mood into a slightly self-deprecating, lighthearted place that he knows his audience loves to bask in. But Primrose isn’t laughing with the rest of them. She’s still stuck on that tiny flicker of a moment, still considering it in her mind. 

Was it really just a coincidence? 

“Alright, that’s a wrap!“ the director’s voice calls out from the speakers connected to the control room.  “Everyone, great job tonight.”

The studio is starting to come down from the high of the show’s lively energy. Crew members begin shuffling about the place in a whirr: moving props, rolling cables, dimming lights, packing up cameras, cleaning up. The pace is quick but practiced; after over twenty seasons on air, it’s an incredibly well-oiled machine. 

Jack is looking at his phone, and he is standing now instead of sitting at his usual desk. It’s a bit of an uncanny sight at first, and Prim is slightly startled by it—by the aloof way that he leans his arm against the tabletop, pristine suit folding at the edges and draping flatteringly against long bones, his legs and perfectly shined dress shoes casually laced one on top of another. Somehow, it feels a little dissonant to his over-the-top public persona—and she realizes it’s because he never stands up that much on the show to begin with. For good reason, too: he would look far too imposing next to most guests, looming over them like a behemoth, and it would most likely humiliate the stars (especially the men) to be dwarfed by such a frivolous, eccentric comedian. 

Primrose begins to look around, hoping to find any last-minute errands she can tend to. As her eyes dart all over the giant sound stage, she hopes to find at least one other person who looks just as out-of-place and overwhelmed as she feels, but to no avail. Upon failing to find someone who might need help, she decides to make herself look busy by doodling on the margins of her pre-show research notes. 

Before she can finish the happy face on the crudely scrawled cat in the corner of her page, a voice cuts through all the ambient sounds of hustle and bustle. 

“Okay guys— can we get a quick second?”

It’s Damon Grey, one of the producers, and Primrose immediately recognizes him as someone that was in the room during her preliminary interview. Alarmingly, he’s fast-walking towards her, and she braces herself, expecting some sort of corrective remark. But instead, he places a hand on her lower back with a jovial smile. Prim smiles back awkwardly, feeling uncomfortable by the sudden contact. 

“Everyone, this is Primrose, our new intern. She’s been shadowing the team for a few days, but tonight I thought I’d give her a proper introduction.”

Prim feels herself flush at the sudden swivelling of heads in her direction. She reflexively looks back up at the set to see if Jack is also looking, but he’s already long gone and—Primrose figures—probably already decompressing back in his dressing room.

“Yes, let’s officially welcome Prim!” a woman’s voice lights up the room. It’s Susan Reid—one of the head writers.

“She’s been helping me out with my pre-show research, coffee runs, and, well—all the little things. She’s been great so far!” 

Susan tends to speak in an overly enthusiastic manner, one that daunts Primrose, making her feel like she’s bound to disappoint. 

The rest of the crew considers her for only a brief second before resuming whatever task they were trying to wrap up prior to the producer’s interruption. Damon gives Prim a reassuring pat on her shoulder, and Susan offers one final smile of acknowledgement in her direction, before going their separate ways. Seeing that the commotion is dimming and that people are beginning to slowly file out of the studio, Prim decides to make her own way back to her car. On her walk to the door, she runs into a taller, chubbier woman with freckles on her nose and sparkles in her eyes.

“Hey, I’m Amy! I’m another intern— er— well I used to be. I just got hired for real like a month ago. I basically just make sure none of the guests get coffee on their dresses in the green room. It happens more often than you’d think!” 

It occurs to Prim that this girl would keep talking endlessly unless deliberately interrupted, which is what she decides to do. 

“Nice to meet you! I’ll be honest— being here feels a little nerve-wrecking, so I hope you can show me the ropes sometime.”

“Girl, of course! Let me tell you a little secret— there’s no real job description. You’ll do everything and anything—I even cleaned the toilets once, believe it or not— so if you have any questions, I’m your gal!”

At the janitorial imagery, Prim can’t help but laugh. This girl seems warm and genuine enough to her, and at the appealing prospect of creating a budding friendship with her new co-worker, she decides to exchange her own secret with her. Well, less of a secret, and more of a sick question that has been bubbling in her since the moment she was hired by that producer. The grin on his face when he said we’ll definitely be in touch, the way he lingered just a second too long when he took her hands in his to shake, and just now—how he snaked himself beside her with his hand on her back, too close for comfort—all of it gave her an unpleasant impression. 

“Actually, um… can I just ask you something…about one of the producers?” her voice comes out as a hushed whisper. Amy is immediately intrigued and eager. 

“Of course! I’ve only been here for a year, but I have plenty of gossip to share.”

Standing just outside the main doors, Prim looks around to make certain of their privacy. The last stream of people talk fervently about making it to the post-show debriefing, before scattering away in haste. Then, they’re left entirely alone. 

“So…the guy that introduced me earlier, Damon, right? He’s been super…touchy-feely. Is that just a thing he does? It’s probably nothing, right?”

Amy rolls her eyes with recognition. “Oh, yeah. It’s not in your head, girl. He’s a bit of a sleaze, but he’s like that with basically every non-middle aged woman here. I’d try and be careful around him…especially because he’s up there pretty high on the totem pole.”

“I see…” Prim considers this confirmation with dread, and suddenly a new curiosity is sparked, one that she tries to put away, but can’t bring herself to.

“What about…Mr. Sinclair?”

“Are you asking if Jack’s a creep, as well? Well, he does like to flatter his female guests—so yeah, honestly I thought he’d be a huge flirt, too! But no, from all that I’ve seen—he’s as sexless and professional as they come! Totally disinterested in the people that work for him. I’m pretty sure he doesn’t even know any of our names.”

Primrose blinks, a little taken by the bluntness, but more surprised by the answer. Sexless? She knows she’s definitely not the only one who’s had a small faraway crush on him, and can only imagine how many co-workers and guests must have at least tried to come onto him in the last five years of his run.

“Really?”

“I mean, the man’s an enigma, so take it with a grain of salt. None of us bottom-feeders know much about him at all. It’s disappointing, but we don’t really see him much outside of the show, or outside of important meetings, anyway— and they rarely let interns sit in on those.”

Before Amy can continue digressing, Prim thanks her as earnestly as she can. They exchange numbers and niceties, before she pushes past her to get to the outside world, where the sky is pitch and void of stars and where the air begins to bite at her cheeks.

Sexless. Totally disinterested in the people that work for him. An enigma. 

It echoes in her head as her breath begins to come out in puffs of cold clouds. But then she remembers those piercing eyes—so intense and so intent on her own—and she knows that the goosebumps that begin to erupt along her neck are not from the November chill.