Blind Date with an Underboss

Katie’s POV

“Katie, just put on the dress,” Olivia yelled at me through the closed door of my bedroom in our small two-bedroom apartment in the heart of Chicago.

“I’m just not sure it’s my style,” I repeated the same excuse, which must have been for the twentieth time in the last half-hour.

“You said that about the last three dresses you tried on. You’re going to have to wear something. You can’t go to your date naked. I mean you could. That would be an amazing first impression,” Olivia said her head hitting the door in a sassy thump, completely exhausted by my procrastination.

“I just think the color sends the wrong message,” I said, trying to stall the inevitable.

You see what my best friend of eight years and roommate Olivia didn’t know is that I might have fudged on my bio on the dating site just a little. Alright, I lied altogether. I shouldn’t even have been on that particular dating site. I didn’t even meet the baseline requirements to have a profile on the site.

The site was designed for those who made met a specific income bracket, and as a teacher, I didn’t even dream of ever brushing the lower bar. But I was tired of the same kind of men asking me for coffee after school, tired of the men who were okay with living in the suburbs—life in the middle of the lane.

Maybe it was the way I was raised, or perhaps it was because I could see myself repeating the same story of my parents. Not that they were unhappy, or necessarily unsuccessful, but it was always the same. My parents had worked at the same school they met at as kids for all of their professional lives.

They were all comfortable, nestled in the same small town in the suburbs of Chicago they'd grown up in. Surrounded by the same couples, who had children at the same time, who did the same things. Everything and everyone was the same. I craved different. I craved mystery. Someone different than the story I already knew so well.

“Katie? You didn’t get the dress stuck around your head and pass out again, did you?” Olivia’s voice filtered through the soft pressed wooden door of our apartment.

If she knew I lied and had gotten myself in over my head, I would never hear the end of it. Olivia wasn’t like me. She was always walking the thin line between dangerous and reckless, and she did it with such confidence that she would never bat an eyelash at my anxiety about my little white lie.

“That’s it, you better cover up what you don’t want me to see. I’m coming in,” Oliva said while she opened the door, barely giving me any time to cover myself up.

“Cute bra,” she commented, winking at me as she pushed by me, plopping on my made bed, pushing half of my decorative pillows off the bed in the process.

“Olivia…” I tried to scold her for coming in like a wrecking ball and destroying my little piece of Zen, the one place in our apartment that she couldn’t completely wreck, but I knew my chastising her would be meaningless. She was a woman with a mission, and at the moment that mission was to get me to squeeze myself into one of her questionably fashionable dresses and boss me around while I applied too much makeup and curled my hair to her liking.

“It’s not about the dresses. It’s not because the black one is too short, or the red one clashes with your only tube of lipstick. You’re stalling because you’re keeping a secret. You’re a horrible liar, Katharine Anne Wagner. You’re not afraid of the red dress clashing with your lipstick, which is awful by the way, and completely washes you out. You’re afraid it’s going to clash with the hives that are creeping up your neck. So, I suggest you confess what you’re keeping inside now,” Olivia said kicking her dirty, studded, heeled boots up on my white down comforter.

“I might have lied about my profile,” I said trying on the red dress again, slipping the silky dress over my head, avoiding my best friend's prying eyes.

“Like you lied about your height or something? So, what? Everyone else does,” Olivia responded, boredom leaking into her voice.

“No… No, I got that one correct,” I said, still avoiding looking at Olivia on the bed as I walked over to my closet to look for shoes.

“So, what did you lie about Katie?” Olivia asked me.

“Which shoes do you think? My nude chunky heels? Or my black stilettos?” I asked.

“Neither. You have terrible shoes that are covered in glue and glitter. You can borrow a pair of mine. Stop avoiding the question. What did you lie about?” Olivia asked, but this time with more intensity.

“That’s not true. Not all of my shoes have glitter. I mean, it’s not convenient for me to wear stilettos to work with five-year-olds…”

“Katie!”

“I joined an Elite dating site!” I said in a rush, turning around to gauge my best friend’s reaction.

Olivia’s face went through all the emotions, starting with surprise and eventually landing on being somewhere between impressed and entertained at my emboldened lie.

“You joined an Elite dating site?” Olivia asked, more to herself, and less to me.

I was breathless, panting, standing in my bright white bedroom, in a bright red silk dress, holding one black stiletto and one tan chunky heel in my hands as my friend processed the mess I had willingly walked myself into.

“Who is this man?”

“His username is Arrow underscore Shot Thirty,” I replied.

“That’s hot. You have a picture?” she asked me.

“It’s on my phone,” I said nodding to the bedside table.

I watched as she picked up my phone. Of course, she knew my password to unlock my phone. I was confident no matter how many times I changed it, Olivia would hack my code. I watched her dark eyebrows that framed her almond-shaped eyes raise in surprise as she looked from my phone to me.

“The red dress, with my nude patten leather strappy wrap sandals. I’ll go get my grandmother's diamond studs. Put on a wing liner, do your eyebrows, and put on mascara. I better grab a tube of red lipstick too, and my bottle of Versace bright crystal. You’re going on this date,” Olivia said hopping off my bed.

“But I lied, Olivia,” I said, stopping her from leaving my room.

“Trust me, Katie, one look at you and he’s not going to care about what kind of money you make. He's not going to want to let you leave him. Ever.”

“How do you know?” I asked. Insecurity washed over me like a cool breeze.

“It’s just a feeling, and you know what I said about my feelings,” Olivia said as she walked out of my bedroom, down the hall towards her room.

Surely Olivia was just gassing me up for my date, knowing that I was nervous and insecure about meeting Arrow. She truly wasn’t serious when she said what she said was she? That one look at me would be all it took for him to never want me to leave his sight? Chills cascaded down my spine in anticipation of the unknown, as I dampened down any spark of hope or want.

Alone in my bedroom, I walked to the full-length mirror that stood just next to my bedside table, picking up my phone. Arrow’s picture still showed brightly on the screen of my phone like a welcoming beacon.

His dark eyes, tan skin, and black hair that was neatly brushed back from his face wasn’t what I loved about this photo. No. It was his smile. Something about how the way the corner of his left lip quirked up like he knew the best-kept secret and the way his eyes sparkled made me believe in what I knew from the moment I saw his profile photo, only to be confirmed by Olivia’s gut feeling.

“Never doubt a gut feeling,” I said to my reflection. Tonight I would meet Arrow, the man I had only seen through a picture on my phone, the man I had only spoken to through the chat on the dating site, the man who I had only known as the name Arrow. Tonight, I would trust my gut.