Living For The City: Do You Meet More Men In Stilettos Or Sweats?

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It never failed.

Despite my best efforts to turn heads, I rarely encountered any eligible bachelors worth a damn.

While I was out here on the dating scene four to five years ago, as a newbie in the city, I went out of my way to be seen. In my attempts to be a bootleg Black Carrie Bradshaw (like every other Black woman writer who moves to NYC from any place much different than NYC), I wore flashy dresses, heels that made my feet hurt, and makeup that made my face break out trying to catch eyes and numbers in lounges with friends. I was in New York, so men were supposed to be at every corner, available and fine. Or at least that’s what I thought.

But despite my sexy bandage dresses, caked-on MAC makeup and smile, I was rarely approached or talked to by anyone other than the people I came with.

Womp. Womp. Womp.

And yet, it is when I’ve looked like I’m on my way to make laundry runs, grab groceries or go to the gym that I’ve been approached most out here. (Seriously, though. Those are just a few of the examples of times I’ve been approached by men while living here.)

And while being approached at your roughest is likely typical for women in most places, I’ve noticed this most here. That’s because before I moved here, I lived in the suburbs of Chicago. I only went out once in a blue moon and drove most places, so my interactions with men for courting purposes were brief and far between after college.

But living here, walking everywhere and taking public transportation, my interactions with men are pretty constant.

Most recently, I stood at the train station, wearing cropped Nike workout pants, an anorak jacket, glasses and a Loc Soc to cover my hair as I prepared to go to yoga. Out of nowhere, a guy walked up to me asking if I knew when the next train was coming. I told him one had just left the station, so it would be another 10 minutes or so. That should have been the end of our correspondence.

“You look very nice tonight,” he said.

“Huh?” I responded, clearly confused.

“I said you look very beautiful tonight,” he stated slowly with a smile.

Considering that I looked as tired as I felt, trying to get it together for headstands and downward dogs before class, I could only laugh and say, “Thanks.”

As he attempted to share more about who he was — a doctor trying to figure out whether he should walk to the bus or wait for the train to get to work on time — and asked me if I had a boyfriend, I quickly told him that I was engaged. He decided to walk to the bus after all.

Standing there during that day, it made me think about the time when I was doing laundry in one of the few clean sweatpants I had left, in an oversized T-shirt, when a man literally hounded me as I quickly tried to gather my undergarments (period panties included…) in the hopes of getting my number so he could take me out on a date.

And then there was the time I was followed through the grocery store, sick as a dog with a runny nose (and a bad attitude) as a guy walked around with me trying to learn more about me like we were on a first date (“Do you go to church?”). I was just trying to get chicken noodle soup and return to my bed.

And then there was the time I met my fiancé. I didn’t look fancy, just hungry. And still, before I left the restaurant I encountered him at while out with a girlfriend, he asked if we could hang out sometime–to my surprise.

Ever since then, it’s been in my more laid-back states, wearing tights with my hair in a ponytail, that my fiancé has complimented me most. Told me that he likes to see my face (as my locs are usually down and in said face), and said that I don’t need makeup. It’s without all the accoutrements that my future husband seems most drawn to me.

Except in sweatpants. He doesn’t like sweatpants three days in a row. But what can I say? I’m not dressing up to be trapped in the house due to Hurricane Sandy (*shrugs*).

Anywho, I say all that to say that I never understood why some men seem to pursue you more when you look or feel run down. Maybe it’s because they think you’re not going to be so high maintenance. Maybe you don’t seem closed off and appear more friendly. Or maybe, just maybe, there is a light in you that’s shining out. You’re more confident than you think when you’re dressed down because you’re stepping out in the most confident of ways–as who you really are. Without the makeup, without the flashy clothes and jewelry. You don’t care what you look like, and you’re showing yourself to the world in a most stripped down way. Who knew that could be so appealing?

Note: This isn’t a recommendation to try and meet men in your most raggedy of states. But if it works…why not?

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