The Curvy's Pretend Holidate

AN UNEXPECTED ENCOUNTER

(Jaime)

Mondays.

Yeah, normally, I was part of that annoying one percent who couldn’t get enough of them, but today, I couldn't care less.

It was just one of those days when I wanted to just lounge in bed and feel sorry for myself… that time of the month for men, you know?

Wait, was that offensive?

I feel like one just can’t say what they have on their mind any more nowadays, but I do apologize if any of you found that offensive.

Anyway... where was I?

Routines.

Right.

Thank God for them, because they were the only thing holding me up right now with everything else around me crumbling.

I started the day as I normally did—early and efficient.

I was up before the sun, and by the time it reared its huge head out of the skies, I had already gone to the gym, cleaned up, and closed two major business deals for Lancaster Premiums… talk about running on super autopilot.

Lancaster Premiums, one of my family’s many companies, was rapidly thriving in its field, but growth required vigilance, and vigilance required me.

I always had to be on the lookout—a million miles ahead, and that was just business.

By noon, though, that spark of productivity had burnt out.

A growing restlessness now gnawed in my head, which was insane, because it wasn’t as though I didn’t have tasks lined up.

Hell, I had an itinerary Aaliyah had sent me from the night before to prove it, but then, all of a sudden, the thought of scrolling through another email chain or sitting through another committee meeting just had my chest tightening.

I got in my car, pulling out of the underground parking lot for a lunch meeting with a couple of investors, but instead of heading towards it, as I had originally planned, I found myself veering in the opposite direction.

I pulled out my phone, instantly dialing up my best friend and partner in crime, Chase Wharton.

Now, Chase was a real devil when it came to having fun and anything closely related to it, and if anyone could get me out of the weird stump I was in, it had to be him.

“You, me, the club,” I said simply when he picked up, going straight to the point as I loosened my tie.

“Yooooooo… what?!!!!!”

The loud, excited cackle that burst out of him was enough to have a faint hint of a smile forming on my face.

“Middle of the day, Jaime? What’s f*****g gotten into you, man?” Chase's voice rang loudly in my ears, filled with amusement, “This one’s new, even for you. Where do you have in mind?”

“Mirage. Call it a scouting mission,” I said evasively.

I mean, it wasn’t entirely a lie.

The exclusive club I had in mind had been on my acquisition radar for months now… I might as well be productive in my quest for a mood-changing experience.

But, back to the Club.

Mirage.

Overpriced cocktails, hard to get into, and exclusively exclusive… were a few of the first things that came to memory when one heard the name.

But honestly speaking, the place had the potential to do so much more.

It was being severely underutilized, and I had plans to acquire it and turn it into an ultra-wealthy destination for people who had insane money and weren’t afraid to waste it—my kind of demographic.

It was going to be the perfect addition to Lancaster Premiums' luxury lifestyle collection.

I just had to get my hands on it.

By the time I pulled up at the entrance of Mirage and stepped out, Chase was already there, leaning against his car with a sly, excited grin on his face.

“Yeah, it’s going to rain fire and brimstone today,” He teased me as we walked into the pyramid-shaped building that was a creative mockup of the Louvre.

The afternoon turned into a blur of indulgence as the manager led us into the VIP section of the building, overly eager to please Chase and me.

Expensive whiskey, music, poker, and completely naked women who eyed us with sheer lust… a couple of them looking like they’d offer us a free, exclusive package if we just gave them the chance…

I’ll be frank, it wasn’t cutting it.

I wanted to leave almost as soon as we had gotten in, but I didn’t want to disappoint Chase, who had been trying for so long to get us to hang out, since we barely did anymore, and so I chugged down as much booze as I could, grateful that at least that was numbing me, leaving me blank.

I don’t know how long we spent there… but soon enough, the whiskey burned less, the forced laughter and fake cheer felt empty, and the women—no matter how stunning and perky— just started to piss me off.

“I need to head out,” I told Chase abruptly, setting down my glass.

He raised an eyebrow. “You serious? But we…we’re just getting started, man… you promissssed,” He slurred.

I reached for him, pulling him up onto his feet. “Come on. I’ve got work to do,” I said, ignoring his drunken smirk and antics.

When we eventually stumbled out, it surprised me to find that it was almost midnight.

I was sober now since I had stopped drinking a few hours ago, but Chase was practically wasted.

I dropped him off at his condo, suddenly filled with the need to pitch a campaign to the board for the acquisition of Mirage.

The owner seemed pretty excited about the prospect of acquiring two billion dollars, and as for me, I was just eager to get started on transforming the place.

The city whizzed past me, colorful lights and festive colors blurring into one, but I couldn’t even focus on it. My mind was fixated on my day, or rather the lack of it.

I’d wasted it away, and now I can’t get any of it back.

But then, all of a sudden, I was hit with this brilliant idea, and as I made a U-turn on the empty street towards Lancaster Premiums, I felt this weird glow in my chest, like I had made the right decision.

I was going to work on my pitch.

******

By the time I pulled into the underground parking garage of my company, the odd mood swing had all but disappeared, leaving me almost back to myself.

Nighttime shifts.

Now, why in God’s name had I never thought of that before?

The peace, the quiet, the complete absence of distractions—it was genius. Double the efficiency, with none of the unsolicited interruptions.

The elevator opened up on the top floor, and I psyched myself for a productive night, only to notice the light coming from around my office.

Someone was here.

For a second, I froze.

All staff should have cleared the building hours ago.

So, who was that creeping around by this time?

I reached into my coat pocket, feeling the familiar, assuring chill of the gun I always kept on me, my senses sharpening.

The soft hum of the air conditioning was the only sound at first, but then I heard it too—

A faint rustle.

Then sniffling.

I stepped further inside, my gaze scanning the room.

And that’s when I saw her.

Aaliyah Walker?

She was sitting at her desk, her back to me, her shoulders slumped in a way I’d never seen before.

The usually composed, put-together Aaliyah looked... lost… broken.

Her hair was slightly disheveled, and there was a half-empty wine bottle on the desk next to her.

A faint hiccup escaped her lips, followed by another sniffle.

Oh, God.

Did I have to go through this?

She still hadn’t noticed my presence… maybe, I could leave while I still had the chance?

I’d never been one for playing hero, but something about the sight of her like that made me pause.

“Mr. Lancaster!” she exclaimed in fearful surprise.

“Aaliyah? What are you doing here this late? Is everything okay?”

She froze like a deer caught in headlights, and for a second, I thought she might bolt, but instead, she searched for words, clearly thrown off by my presence. “What are you doing here, boss?” she mumbled. Her tone was sharp, but she instantly winced, an apologetic look crossing her features. “Sorry. I… I just needed some space, and this felt like the right place to be.”

I raised an eyebrow, trying to figure her out.

Was she being honest?

Or was this something more?

The office wasn’t exactly the top pick for people looking to escape their troubles, and I let her know this, but who was I to judge?

“I’ve got some work to catch up on, and if I’m being honest, some company wouldn’t be the worst thing right now. Stay, Aaliyah,” I said gently, surprising myself. “And if you want to talk about what’s bugging you too, I’ve got a few minutes to spare.”

What was I doing?

I needed to stay as far away from her as I could, but instead, I was offering therapy sessions?

Her lips parted, hesitation flickering in her eyes before, to my surprise, she started to talk.

I wasn’t expecting the flood of words that came next.

She told me about her cheating boyfriend… how she kicked him out, breaking her sobriety. By the time she was done, the tears were full-on streaking down her face, and I’d be damned, but it was like someone punched me in the gut.

Seeing her so torn up—hell, I didn’t know what to do with that, given that comforting people wasn’t exactly my strong suit.

But I couldn’t just stand there, either.

“I’m sorry, Aaliyah,” I said quietly, stepping closer. “Is… is there someone I should call? Your sponsor? A friend? You really deserved better than that.”

Her bitter laugh cut through the room as she sank to the floor, her brokenness making my chest ache unexpectedly. “Yeah, well, the universe doesn’t seem to agree,”

I shook my head, crouching to meet her at eye level, the urge to say something—anything—pushing me forward.

I faintly wondered how my family would react if they caught me in this setting, fraternizing with the enemy like this,

But in that moment, it all seemed irrelevant… inconsequential.

I just wanted her to be okay.

“Listen to me, Aaliyah. You’re smart, talented, beautiful, and strong. Logan was an i***t to lose you.”

“I know,” she smirked, but the tears didn’t stop. She tried to joke, but her voice cracked, and a sob slipped. “I just wish the grieving part would be over soon so I can put all of this behind me and move on.”

Her words hit me harder than I expected, and without thinking, I reached out, wrapping her in my arms, with her permission, of course.

It wasn’t the most professional thing to do, but screw professionalism.

She needed someone, and I was here.

That was all that mattered.

“There, there,” I murmured, my voice softer than I thought possible. “Everything’s going to be alright. I wish there was something I could do to make you feel better…”

I felt her stiffen slightly before relaxing into the hug.

She clung to me for a moment, and I let her, holding her as the weight of her sadness slowly lessened.

It was almost like magic, for as her grief seemed to drain, so did the rest of my depressed state.

Aaliyah pulled away from me, way better than when I first came in, “Actually, Mr. Lancaster… there is something you can do for me.” She told me determinedly.

“What’s that?” I found myself asking, eager to help in any way I could.

“You could just… help me forget everything by being my Holidate. My pretend Holidate.”

Her what?

“My Holidate,” she repeated the words, her cheeks flushing in embarrassment as she told me about some Christmas movie starring some famous actress.

“You’ll be my fake date for the holidays, basically pretending to be my boyfriend just to make me look less pathetic in front of everyone who expects me to show up broken and alone.”

Oh.

I stared at her, torn between amusement and sheer disbelief.

When I finally managed to find my voice, I shook my head at her. “You’re drunk.”

“Oh, not that drunk,” she shot back, waving a hand. “Okay, maybe a little. But I’m serious. It’s perfect! You’ve got nothing to lose, I’ve got everything to gain, and we both avoid awkward holiday small talk with strangers.”

I opened my mouth to argue but stopped short when I saw the hopeful look in her eyes.

This was stupid.

Insane, and very dangerous for her… what she was proposing, but what the hell, she had stopped crying and feeling sorry for herself at least, and it all had to do with her strange request, which she had oddly defended with some very compelling points.

I laughed, shaking my head at her, “This has got to be the most ridiculous thing I’ve ever heard, Aaliyah…” I told her honestly, “But what the f**k, I’ll do it,” I said.

“Really?” Her eyes lit up, and she looked genuinely happy for the first time that night.

“Yes. I’m serious.” I rose to my feet, pulling her up and swiftly hauling her over my shoulder before she overthought it.

The surprised ‘oomph’ that escaped her lips made a pleased smirk form on mine.

Clearly, she had underestimated my strength.

I’d be honest, this was the first lengthy conversation I’d had with my assistant, and while it was… raw, and open on her end… it was also the most fun conversation I’d had in a while.

It showed me a side of her that I wanted to get to know more… a side that I wish I could know more of…

Too bad she was the enemy.