The Curvy's Pretend Holidate

ON THE THIRD DAY OF CHRISTMAS A DRUNKEN NIGHT MADE ME PROPOSITION MY BOSS

***Slight trigger warning***

(Aaliyah)

I sank to the floor in a messy heap, my back pressed against the door, my chest heaving with quiet, shuddering sobs.

I don’t know, but now that the house was stripped of all of Logan’s presence, the house felt eerily silent… naked.

Trust me, it was a relief, because I knew how worse it could be having to be that vulnerable girl who took his cheating ass back… to have him walk the halls and parade my rooms rubbing the fact that he got away with betraying me in my face…

What I didn’t understand was the heartbreak that continued to grip my entire being despite having mentally accepted my fate.

Of course, with the heartbreak came the shame. Shame for crying over someone so utterly undeserving, when what I ought to have been doing was celebrate my triumph at how wonderfully well I had handled him and kicked him to the curb.

But the tears wouldn’t f*****g stop.

They came in torrents, reminding me of everything that could have been,

Of that tainted illusion, I was clearly holding on to.

I took in a shuddering inhale to remind myself to breathe, to soothe that aching, ripped-out, pain in my chest.

For what felt like hours, I let myself break… let myself cry until I didn’t think I had any more tears left within me. Eventually, I wiped my face with the sleeve of my sweater, the fabric dampening against my skin as I sniffled, straightened my spine, and then slowly forced myself to my feet.

Sitting here, surrounded by the freshness of Logan’s betrayal honestly wasn’t going to help.

I grabbed my coat, my keys, and my wallet, barely caring about my tear-streaked face and the puffiness under my eyes.

I just needed to get out.

The cool night air hit me like a slap as I stepped outside, clearing my head just enough to make me painfully aware of my surroundings. On second thought, I decided against using my car, preferring to walk around instead, so the fresh air would ground me and get me out of my head.

But all it did was remind me of everyone else’s happiness.

The city was so alive with Christmas cheer, with strings of lights twinkling in every shop window, tiny choirs singing in corners, and couples strolling arm in arm, laughing and stealing kisses beneath wreaths and mistletoe, the f*****g snow that always used to be my favorite time of year…

My heart clenched at the sight, a pang of longing that cut deeper than I wanted to admit hitting me.

Those couples should have been me and Logan.

We should’ve been planning our holiday, sipping cocoa, talking about the future.

Instead, I was here—alone… broken.

I wandered the streets aimlessly, feeling that familiar urge to numb my pain lurking like a long-forgotten shadow.

It had been four years since I’d last touched a drink.

Four years of hard-fought sobriety that had been surprisingly easy even with everything I constantly went through.

But tonight, that urge was even more tempting than usual… more insistent, cruel.

I found my feet dragging several times as I passed by cozy, inviting-looking bars, and like the devil’s advocate, they just kept appearing in their numbers.

“No.” I muttered fiercely under my breath, clenching my fists at my sides as I willed myself to stay strong, to fight it. “Not tonight. Not like this.”

The pull was so f*****g strong, but one thing kept holding me back...the fact that I might meet someone I knew in there and have to go through the rehab process all over again.

But my mind apparently had a plan to deal with that little hitch.

Before I knew it, I found myself ducking into a nearby wine shop, because why the hell not?

I could have as much wine as I wanted all to myself that way anyway.

I grabbed a bottle without even looking at the label, handed over some cash with trembling fingers, and stepped out onto the street with my secret package.

It was at that moment that I wished that I had taken my car, but hey, I was a responsible drunk, and I knew the dangers of drinking and driving.

But I couldn’t go home.

Not yet.

That house was suffocating me, but the good news was that I knew of another place where I just could get away with renewing my bad habit. And so I continued to walk, and after what felt like ages, I got to the underground parking lot of the tall building where I worked, Lancaster Premiums.

Yeah, I know… office… bad idea, whatever, but this place was completely deserted at night, save for the cameras, and I knew all the few blind spots.

This was really the only place I could think of where no one would judge me or ask questions.

The office was dark and cold when I successfully snuck in, but I welcomed the emptiness.

It reflected how I felt inside.

I curled up in my desk chair, clutching the bottle in one hand, my phone in the other, and with each sip of wine, I scrolled through i********:, deleting every picture of Logan… every memory, every reminder of the life I thought we were building together.

Each deletion felt like ripping open an actual wound, but it was the only way I could breathe.

The bottle was halfway gone when a sound startled me. A door creaked open, followed by soft footsteps.

Shit.

Someone was here.

My heart leaped into my throat, panic sobering me up just enough to make me shove the bottle under my desk.

I wiped my face with the back of my hand as I turned toward the noise, mentally preparing an explanation for the late-nighter.

Imagine my surprise when the figure came out of the shadows only to reveal none other than my boss and the CEO of Lancaster Premiums himself,

Jaime Lancaster.

“Mr. Lancaster!”

I shot to my feet with a start, only to collapse on my chair again from a spell of dizziness, and the poor confused man, bless his heart, was by my side in a minute, trying to figure out what was wrong with me.

His tall frame hovered over me, brown eyes narrowing slightly as he took in the sight of me.

“Aaliyah?” His voice was low and calm, laced with curiosity. “Aaliyah, what are you doing here this late? Is everything okay?”

I froze, scrambling for an answer, but the alcohol dulled my usual quick thinking. “What are you doing here, boss?” I mumbled back, my tone a tad sharper than I had intended.

Even in my state, embarrassment and frustration rolled off me in waves, further heightened by the wine.

“Sorry,” I apologized sheepishly, “I…I just needed some space, and this felt like the right place to be,” I finished contritely, avoiding his gaze.

“Well, you know the office isn’t exactly the best place for that, right?” He came closer to me, looking as pristine as ever in his suit.

At this point, I was pretty sure he wore them to bed if I was being honest.

Heat rushed to my cheeks at his question, and I nodded, trying to stand to my feet.

“I have some work to catch up on, and if I’m being honest, some company won’t be bad. Stay, Aaliyah.” He said gently, “And if you want to talk about what’s bugging you too, I’ve got a few minutes to spare.”

I must have really been wanting to vent to someone, for before I knew it, my mouth was opening up, pouring out the embarrassing words, “Fine. My boyfriend cheated on me. I kicked him out. I am a mess, and I just broke my four years of sobriety on alcohol.” I rambled,

“I just… I needed a place to hide so no one would see me unravel, you know?” The tears were streaming down my face now, and I noticed how uneasy it made my playboy boss.

Seriously, it would have been an incredibly hilarious moment if I didn’t feel so broken.

Mr. Lancaster’s expression softened as he took a step closer, “I’m sorry, Aaliyah. Is… is there someone I should call? Your sponsor? A friend? You really deserved better than that.”

Wow.

His soft tone caught me by surprise, but I tried to act all tough.

A bitter laugh escaped my lips as I sank to the floor, and I almost winced at how the hollow sound filled the otherwise empty room, “Yeah, well, the universe doesn’t seem to agree.”

A silence settled between us, one that was calm, and peaceful enough to have me open up even more.

I like to think that it was the wine, but it felt more like it had to do with the vulnerability of the moment instead, for I found myself saying the words I’d been too afraid to admit out loud. “You know what’s sad? I had seen the signs and overlooked them anyway. The only reason I stayed with him for so long is because I thought… I thought no one else would want me.”

My boss frowned. “Come now, that’s not true, Aaliyah.”

I shook my head, looking away with an amused scoff. “You sound like my friends right now, Mr. Lancaster. But here’s the thing: Guys like Logan don’t fall for girls like me, not unless they’re trying to gain something. I should have known that it was all too good to be true. To think that I had only kept him for my family’s Christmas reunion… and we didn’t even make it to that stupid event, and now everyone’s going see me, and think I made the whole boyfriend thing up.”

His jaw tightened, but he didn’t argue. Instead, he crouched down, meeting me at eye level. “Listen to me, Aaliyah. You’re smart, talented, beautiful, and strong. Logan was an i***t to lose you.”

“I know,” I smirked proudly, even as a tear slid down my cheek, “I really am a full package, aren’t I?” I tried to joke, but a sob got caught in my throat, “I just wish that the grieving part would be over soon, so I can put all of this behind me and move on.”

“Oh, Aaliyah…” Mr. Lancaster whispered huskily, “You know what? You look like you could do with a hug right now. I’m coming in.” He barely gave me time to react before he was wrapping those buff, yet incredibly soft, warm arms around me, offering me the comfort I didn’t even know I needed. “There, there,” He cooed softly, “Everything is going to be alright. I really wish that there was something I could do to make you feel better…”

I wanted to push him away, but it felt… nice.

I savored the hug as much as I could, thanking the stars that they had at the very least provided me with someone to comfort me in this trying moment.

A reckless plan formed in my head at his offer just as I pulled away. “Actually, Mr. Lancaster… there is something you can do for me,”

His brows furrowed. “What’s that?”

“You could just… help me forget everything by being my Holidate. My pretend Holidate.” I shot him with the words.

My boss froze, turning slowly to face me.

I could see the confusion in his eyes, in how his lips twitched as though he wasn’t sure whether to laugh or be concerned. “Your what?”

“My Holidate,” I repeated, my cheeks burning, though I wasn’t sure if it was from the wine or the sheer audacity of my suggestion. “You know, like in that cheesy Christmas movie with Emma Roberts. 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.”

Mr. Lancaster’s mouth opened and closed like he was trying to find the words. Finally, he settled on, “You’re drunk.”

“Oh, not that drunk,” I 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. Lord knows I can’t go through it again. Plus, I know all about your flings… and hooking up with any of them in this magical period is going to give them the wrong idea… have them thinking you want commitment!”

I watched him visibly shudder.

I was close to breaking him!

“Aaliyah…” He ran a hand through his perfectly styled hair, his usual confident composure cracking just slightly, “This is just the wine talking,”

“Maybe,” I admitted, shrugging. “But come on, it’s also genius, don’t you think? Anyway, the point is, it’s a win-win. You get to dodge girls with hidden agendas… I get to make my family eat my farts… and their words when I pull up with you, because look at you—” I stopped myself just in time, taking a deep breath. “Uhm, you get the idea. So, what do you say?”

For a moment, Jaime Lancaster just stared at me, his expression unreadable.

I braced myself for the imminent lecture on professionalism and whatnot. But instead, he did something I wasn’t expecting.

He laughed.

Not a polite chuckle or a dry, businesslike laugh, but a real, deep, belly laugh that echoed through the empty office and sent a ripple of warmth through my chest.

“This has got to be the most ridiculous thing I’ve ever heard, Aaliyah… but what the f**k, I’ll do it,” he said, shaking his head.

“Really?” My eyes lit up like golden saucers, my heartbreak momentarily forgotten.

“Yes. I’m serious.” He rose to his feet, pulling me up onto mine and hauling me over his shoulder, making a surprised ‘oomph’ escape my lips at how easily he had lifted me. “Now, come on… let’s get you home. I know you’ll regret this moment tomorrow, but no take-backsies.”

I scoffed in amusement.

Seriously, why the hell would I want to take it all back?

It was exactly what I wanted!