The Underwear Drawer: Coulda, Woulda, Shoulda

Written by: Langston John Blaze

In dating, failure to take certain risk result in a whole lot of coulda, woulda, shouldas. In the last year, my confidence level when it came to dating coulda, woulda, shoulda took a dive in a waterless pool and hit the surface like one of those cartoon characters from Looney Tunes. What was happening to me? Had I been hurt so many times I’d forgotten the basics of engaging conversation and coming off natural? The first test of my need to be confident again was speaking to a very handsome guy I’d seen around the last few weekends.

I didn’t know his name so I started calling him Grey. A friend of mine pointed out to me that he had grey eyes, which did not make him any easier to approach. In my first encounter with Grey, I tried the most outrageously pathetic move made popular in the Reese Witherspoon sequel to Legally Blonde and made famous by the actress Jennifer Coolidge; The Bend and Snap. I noticed Grey standing next to me the entire night at a popular lounge in Atlanta, which felt more like a club atmosphere. I knew I wasn’t interested in trying to approach a guy at a club, but for where I was mentally, I needed the practice. Nonetheless, this was more like hands on work. I was attracted to Grey; well, based off the way he presented himself.

As he stood beside me, I casually dropped my cell phone on the floor to see if he would pick it up. To my surprise, as I bent down to get it, Grey beat me to it and handed the phone to me. I smiled directly at him, but I was so mesmerized that he made the effort to pick up my phone, I flaked on any other action. Damn! I remembered how to create a situation to engage conversation but now I’d lost confidence to carry the plan through?        Upon that missed opportunity, I had several chances to make a move. The following week, I spoke to Grey for the first time. “How do you put up with him?” I said in his ear, commenting on a popular Djay who was more known for groping people in the club than Djaying. He’d been groping Grey and I both when I decided to use his antics to my advantage. “He’s a hand full,” Grey replied, giggling. Seconds later, I saw him leaving after telling a friend goodbye. I headed out with my newest friend, Kel, a socialite in Atlanta, who seemed to know how to get guys, while maintaining his friendly fashion forward persona.

Meanwhile, Grey was standing outside, waiting for valet. Kel practically pushed me to talk to him, but…I couldn’t. I didn’t have that thing that made me feel so ballsy enough to talk to any guy I wanted. I had been hurt; scarred by guys I’d dealt with in the past. Rejection didn’t seem to be my problem. It was what occurred through the get-to-know-you phase. In the past, I’d discovered so much bull shit with men. For some idiotic reason, I stayed around, time and time again, letting the bull shit intoxicate my senses. I’d never got it until it was too late, but bull shit definitely had a stench.

That night, I drove Kel home. I told him how much I regretted not talking to Grey. Hell, I didn’t even know his real name. “Be yourself. Next time you get the opportunity to talk to him just say “Hi, my name is Langston. I’ve seen you around before. What’s your name?” I smiled. Kel made it sound so easy. Truthfully, it was. However, in life, I knew my greatest fault was making things harder than what it had to be. Life isn’t always black or white. Some times, there’s a grey area. You don’t always get a second chance for a first encounter, and eventually, the coulda, woulda, shouldas become more of a heartbreak than the actual emotion.

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Thanks !

Thanks for sharing this, you are awesome !