Blind Date with an Underboss

Chapter 2: More than just Liquid Courage

Katie's POV

“Here we are, ma'am." My Uber driver said to me as he pulled his hybrid car up to the curb of some swanky Chicago street.

“Thank you, Steve," I said as I opened the door.

“Good luck on your date," Steve said as I stuck my foot out of the door, avoiding the pooling water from what I hoped was just rain, that had occurred over the last few days and not some other liquid pooling between the street and the curb. The shoes I had borrowed from Olivia were dangerously high, as was the slit in my borrowed dress. I offered Steve a nervous smile, as my stomach flopped in anticipation, and left the comfort of the vehicle.

The evening breeze of the Chicago spring evening was welcomed on my flushed skin as I avoided the brush of other people on the sidewalk. I had asked Steve to drop me a block away from the affluent restaurant I was meeting Arrow at. I wasn't sure how it would look for the woman who I had posed myself to be to show up in an Uber, plus the walk would allow me to clear my head. To focus. To catch my breath and settle my nerves.

“Katie?" A familiar voice said my name from the crowd of fellow chi-town citizens.

My heart immediately sank. I prayed that if I didn't turn around and recognize the man who called out to me, perhaps he would just think it was someone who looked like me, and then it would be something we could laugh about later. But no. Not this man. He was determined. No more than a moment after I heard my name called, I felt a hand on my bare arm and the face of the man I knew so well filled my vision as he stepped in front of me on the busy sidewalk.

“It is you!" Sam said, pushing up his glasses, which were too big for his face. His sandy blonde hair was loose around his shoulders, something I had once found attractive.

“Hey, Sam!" I said, trying with everything inside of me to sound light and casual.

“You look good," Sam remarked as he took his time appraising my attire Taking too much time on my exposed thigh through the slit.

“Thank you. But I need to be going. I'm going to be late," I said, forcing a friendly smile to my face, something that expressed kindness, but not too much kindness.

“Where are you going?" Sam asked, jealously leaking through his casual, friendly tone.

“Just drinks with a friend," I said, shrugging my shoulders.

“Drinks with a friend dressed like that? Who's the friend?" Sam asked, the jealously he had tried to mask was no longer so hard to hear.

“Olivia and some of her co-workers," I lied, which normally would have been unbelievable, but this lie came out easy and was convincing enough for Sam as he relaxed slightly, in the past Sam would have insisted that he would have come with me regardless of who was in attendance constantly fearful that I was going to meet some other man.

“Cool," he said his coined phrase.

I held back my eye roll as he stood to the side, taking it as my cue to continue my trek to the restaurant, but I was naive. I shouldn't have believed that he would let me off with just a 'Cool.'

“I'll walk with you," Sam said, stepping up even with me.

“No. I'm fine, trust me, I'll see you at work tomorrow," I said, trying to outwalk him, but his long legs were hard to outwalk.

“I'd feel better if I knew that you got there safely," Sam said, shoving his hands into the pockets of his jeans that I had bought him when we were dating.

Sam made it a habit to wear everything I had bought him, like some sort of shrine to our relationship. Even though our break-up was his idea, he had regretted his decision almost immediately and had been trying to rectify our relationship for almost two years. No matter how many times I had told him it was never going to happen Sam was determined to wear me down.

Admittedly, there were days that I had been tempted purely out of exhaustion to just give in to his pursuits, to just go back to the mundane. Perhaps if he hadn't broken up with me, I would have been Mrs. Sam Wentworth by now. Repeating my mother's story, a teacher married to a teacher, living in a three-bedroom two-bath suburban house, commuting to the city to teach together. Perhaps I would be pregnant with our first, discussing baby names. But my life was meant for more. I was meant for more, and my more was just a block away.

“You know what, Sam?" I said starting my confrontation with the man I had just allowed to push down every boundary I had ever erected. “I really am okay, thank you so much for wanting to walk with me."

“I don't mind. It'd be nice to see Olivia again," Sam insisted.

“No," I said boldly, clutching the small jewel-encrusted purse Olivia lent to me that only had enough space to hold my phone and borrowed tube of red lipstick.

“I insist…"

“I said no. Sam, and my no is final. Don't follow me. I'll see you in the morning," I said, speaking in my teacher's voice, which shut Sam down completely.

I walked away without looking back and not feeling his presence behind me. A smile of success filled out my face as I had done something I hadn't thought I was capable of doing. I thought I might need a shot to find my liquid courage, but all I needed to do was face my ex before meeting my blind date in order to find my courage.

I practically floated to the restaurant, and before I knew it, I was standing in the brick entrance of the candlelit, fancy eating establishment. Now armed with the boldness I earned from saying no to Sam, I was completely confident that I could meet the man who had let loose a swarm of butterflies in my soul.

“Hello, miss, how can I help you?" the beautiful hostess who was dressed in a skintight black dress asked me with a glowing smile.

The insecurity I had been feeling moments before my encounter with Sam threatened to overtake me again, but forcing it down, I returned her smile with just as much excitement as I felt.

“Hi, I'm here to meet a man, he has a reservation under the name Arrow?" I responded. Her eyes lit up in recognition of Arrow's name.

“Oh, yes, of course. Mr. Arrow, isn't here yet, but you can follow me, and I'll show you to his table," she said as she guided me into the restaurant.

It was more beautiful the deeper she guided me into the opulent establishment. Tables had fine linen of black instead of white. with Candles hung off of the red brick walls, shining a soft amber glow. It was more than just romantic, it was seductive, with the smell of roses mixed with jasmine wafting in the air. This, in turn, mixed with the aroma of herbs, and the variety of entrees ordered by the patrons.

The boldness I had been feeling suddenly faded, and I was overcome with the feeling that I had, indeed, gotten in over my head when she showed the reserved table, hidden in a room of its own. Dark purple wisteria hung from the ceiling. In the center of the room was a single round table with a deep red linen cloth, with crystal flutes and china.

“Mr. Arrow insists on the finest, so we reserve him the private dining room," the hostess explained.

“He comes here often?" I asked.

“Not as often as we'd like," she said with something akin to envy in her voice. “You're a very lucky woman."

I stood in the room as the hostess left me, suddenly feeling completely unprepared for the kind of man who would be joining me.