That time I was mistaken for a prostitute
The “Pretty Woman” moment that happened to me in real life

My name is Shamontiel, and I like hooker heels. I can laugh about it now, but I was (mildly) offended the first two times a man accused me of wearing them. The first time I heard it was from my brother, who teased me for wearing glass slippers the day of my college graduation. But what else was I supposed to wear with a periwinkle skirt set? I had to find something that went with this outfit, and my Cinderella shoes were cute.
I’m not a shoe fanatic like my mother, but I do like a good pair of heels. A college friend of mine told me that everything about me seems a little rough around the edges, so he was stunned to see me walking around a dorm room with bare feet and perfectly polished toenails.
It’s rare that I go to a spa or get a pedicure, primarily because I used to give everybody else manicures and pedicures throughout elementary school and high school — my grandfather included. But I’ve always been a stickler about neat feet. And if I’m wearing heels, I’m damn sure not going to have chipped toenail polish.
Even before the twisted ankle that made me guy up on heels, my shoe collection almost got me arrested. I was on my way to work, put on my favorite black sweater dress that I scooped up before my mother could donate it to charity, and climbed into a pair of knee-high black boots to match it. The sweater dress was a little longer than my knees so the top of the dress and the boots almost kissed when I walked. I thought it was a fairly simple outfit to wear to work the night shift at the newspaper I was employed with at the time.
Before I headed out the door, I got an email from one of my past interviewees. He was in town during a music tour and wondered if I was available to hang out. I was ecstatic. He was cool as ever, funny and with talent dripping from his fingernails. I agreed to meet him in downtown Chicago an hour or two before my work shift started. I headed downtown in that outfit, texting him a couple of times to let him know how close I was.
Although he’d been to Chicago before, he wasn’t super familiar with the neighborhood. Meanwhile, I’d spent 75% of my life in the Loop or the Magnificent Mile. I could walk those blocks in my sleep. He suggested that I meet him in his hotel lobby, and I agreed, rerouting from a nearby coffee shop (where we were supposed to meet) and heading his way. I got to the lobby before he came downstairs and flopped down in a chair.
A few minutes later, he came downstairs and I stood up to greet him. Instead of heading toward the lobby door, he sat down on the hotel couch so we decided to catch up right there. I noticed a couple of men nearby, but I didn’t pay them as much attention as my interviewee friend did. I was too busy chatting and catching up on his music career, but I eventually noticed he stopped making eye contact with me.
“Let’s head out,” he finally said.
I followed him, still talking a mile a minute.
We strolled to the coffee shop a few blocks away, got our order and decided to sit outside. It was a cool day but not so cool that I needed a coat over my sweater dress. In the middle of us talking, I watched the smile drop from his face and his face harden. I turned around to see what he was looking at, and I recognized the same two guys from the hotel lobby.
“That’s the same two guys from the lobby,” he mumbled under his breath.
“Are we being followed?” I said and got ready to laugh.
He didn’t laugh. He just stared at them. I looked over at the two men, who seemed far more interested in me than him. I was clearly missing something. I watched an eye standoff between the three, and then finally the two men walked away.