My Insufferable Boss

12

I fix my dress as I cross my ankles waiting for Winston. I was wearing a sleeveless floral ruffle wrap maxi dress that fell to my ankles, it was slightly shorter from the front and longer at the back.

He had just texted me that he's 2 minutes away so I came down waiting for him outside my building.

I was slightly nervous about tonight, I haven't been on a date in over a year not to mention Winston is my colleague who I see every day and a close work friend at this point so if it doesn't go well, I'm screwed. I'll have to face him at work every day and the embarrassment would eat me alive surely.

Winston's black car pulls up, I can see him beaming through the windows. I smile as I reach for the door.

"Hi," I say closing the door behind me. Winston was wearing a full sleeves button-down dark green shirt and dark blue jeans, his hair was styled more than usual, his green eyes sparkling as he smiled.

"Hey, you look stunning" Winston hands me a white rose and I smile taking it.

"You look great yourself" I compliment him instantly his smile grows wider.

"So where are going?" I ask.

"There's this really nice Italian spot a couple of blocks from here. Hope that's alright with you?" Winston smiles.

"Yeah, I love Italian" I smile.

"Great" Winston looks over at me one last time before driving away.

....

"So tell me about yourself," Winston says taking a sip of his drink.

I laugh, "I feel like you already know me well enough, tell me about you. Did you grow up around here?". One thing I'm insanely good at is avoiding questions about myself and basically turning the conversation on the other person. I may be extroverted but I don't feel like blurting my life story or my struggles to every second person. I'm actually quite a private person.

"No I was actually born and raised in Florida, I moved to New York for law school" Winston nods.

"Are you an only child?" I ask.

"No I'm the youngest of 8" Winston chuckles.

My eyes went wide, "8? Oh my Lanta, I hope your mom is okay"

Winston laughs, "Oh no she's great. She actually wanted 12 kids but dad made her stop at 8 because it was literally going to kill her"

I shake my head in disbelief, "no disrespect to your mom, I have so much admiration for women who have children especially those who have multiple like I don't see the point?" Winston laughs, "It's so excessive, I don't see myself ever wanting to be a mom that bad that I willingly want to birth children" I shiver thinking about labor. It is truly one of the biggest fears of my life.

"So what, no kids for Maria Reynolds ever?" Winston looks at me amused.

I shrug, "At this stage of my life, yeah probably. I might adopt one day but childbirth no" I shake my head.

"I actually want to have at least 6 kids of my own" Winston says. Yeah, this is never going to work between us.

"Wow, why?" I cover my mouth with my hand as soon as it comes out, the tone of my voice was so bitchy and mean.

Winston laughs, "I just love the idea of a large family, I want my children to have the same upbringing and family values as I did growing up" Winston shrugs.

"So what are the age differences between you and your siblings?" I sip my wine.

"My oldest brother Tyler is 47, then came Alex who's 44, then May she's 38, then Ryland who's 35, then Kara who's 34, then Jason who's 33 then there was Charlie and I and we're 31," Winston says.

"Wait you're a twin?" I ask surprised.

"Yeah" Winston laughs.

"Oh wow, are you identical twins?" I ask.

"Yeah, we are" Winston smiles.

"Oh my, that's so cool. Wow, I'm so impressed with your mother having all those kids basically back-to-back insane" I smile.

Winston smiles, "Yeah she's the best, after Charlie and I though, it was rough for her the doctors had to sit her down and tell her she physically can't do anymore which was really heartbreaking for her because she was so close to her ideal family she always wanted"

I tilt my head, "Aww that must've been hard for her"

Winston nods, "What about you? How many siblings do you have?"

"Oh just me and my younger brother," I say.

"How old is he?"

"He's 18, a freshman at college" I shrug.

"That's quite a huge age gap, you must've practically raised him growing up" Oh you have no idea.

I smile, "Yeah kinda".

....

Winston offered to walk me upstairs to my apartment because he's a gentleman. He really is the epitome of a nice guy, he's so lovely.

We reach my door and I awkwardly smile at him, "Thank you so much for dinner"

Winston smiles, "I had a great time tonight"

"Me too" I smile.

We stand there awkwardly not knowing what to do. I lean in for a hug, I wrap my arms around his neck and he wraps his around my waist. After a few seconds, we pull away.

"Well goodnight" I smile moving to unlock my door.

"See you on Monday" Winston smiles walking away from me.

I walk into my apartment and lean against the door. I cringe to myself, that hug was so uncomfortable oh my lord but I'm glad I hugged him before he could lean in for a kiss, that would've been worse.

The date was nice, it really was but it more felt like I was out to dinner with a friend which technically I was. Winston is a wondrous guy and I guess I'm fucked up in the head not to see how guys like him only come around once but there was no chemistry there. There never has been a spark since the minute I met him and wasn't there tonight and that's not to say it's because of Winston, we just don't click and vibe in a romantic way. That shouldn't be a problem except we work together. If he asks me out again, which I think he would not to sound conceited but I think he thinks we matched really well but for me, all of that was just friendly things but if he asks me out I'll politely turn him down by making some excuse. I sigh, why do I feel so bad? I can't force myself to like someone no matter how spectacular they are, if we don't vibe then we don't vibe.