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Most Embarrassing Moment EVER.


If you’ve read my previous blogs, you’ve learned one important thing about me already–Awkward is my middle name.

Actually, it’s Lee. But, I could go to the courthouse and get it changed, because it would be F-I-T-T-I-N-G.

Awkward is as awkward does, yes?

From Adam and Eve grabbing fig leaves to ‘hide’ their nakedness as God approached to Kanye West at any public event where a microphone is nearby, there is awkwardness in all of us.

Flawed. Imperfect. Impure. And yet, our attempts to improve are still sometimes commendable.

It’s tough for me to pick just ONE awkward moment, but if I have to, I know which one I’ll use. (Please don’t judge me until you see me doing something like this again. Then, you have the right to call me out.)

It goes like this…

When I was 10 years old, I visited my Dad, Step-Mom, and Sisters on weekends. They lived in a small community about an hour north of Monticello. My family bonded over trips to a neighboring creek, cook outs, and the occasional drive to a movie theater in Danville. We had good times, and Dad always put me up to stuff.

I can safely say that I’ve swam with water moccasins, peed on electric fences, rode a not-so-wild boar fittingly named Wilbur, and ate muscadine grapes well before being seasonally ripe. But…none of this compares to the prank my dad put me up to Winter 1994.

He said, “Brian, I bet you won’t do something.”

Never one to back down from a challenge, I replied, “Name it.”

Dad came out with a dress, high heels, and the works.

(You’re probably wondering where this is going. I was too…)

“What’re you doing with that dress?” I asked.

“I think this would fit you,” he joked.

“Sure sure,” I played along. “The shoes might be a bit small.”

He said, “You want to play a prank on a your granny?”

(I’m not a punk, I promise. It was an experiment.)

“Just for fun,” he encouraged.

I stuttered and stammered over the next few minutes, and felt like I took all day to bite. Finally, I told him to hand it over. My step-mom said I should work on my act.

(I wanted to know just how a lady in a sundress acted. But, that was the beauty of it…I was too young to really know, or, understand any of it. Other than, my dad had dared me. And, I couldn’t refuse.)

I slipped the 1980s, floral print cotton dress over, and my step-mom playfully joked, “I’ll zip you up.”

(Now, I think about this today, and I can’t help but get embarrassed.)

The shoes DIDN’T fit. Cinderella gone terribly wrong. Horribly, frightfully wrong. But, we put them on anyways. And, this is where it gets really interesting. We drove to granny’s house (well, my step-mom’s grandma’s house…so that would make her my great-step-granny’s house…yes. I got that right.), and Dad gave me the foolproof plan. I was to march to the front door with dress, purse, high heels, even tights, lip stick, and a derby hat on, and PRETEND to be her home health nurse.

**I apologize to any nurses in advance that get bad reputations because of cross-dressing, 10-year-old boys like this one.

So…the prank started when I knocked on the door. Granny answered, and Dad waved and sped off. I remember foggily entering a warm, quaint house and being urged to sit down. She said something about taking medicines and not taking some as often as she should. (My moral compass flipped on at that point for me. Guilt. Shame. The works, for what privacy of hers I was invading.)

I started to speak. To say, “Oh that’s all right,” when, I remembered my voice was starting to change. To sound manly. So, I remember having to raise it a few octaves intentionally and coax out a few pleasantries from my vocal chords.

Longest 15-20 minutes EVER.

I said something about needing to leave. Stood, noticed a run in my tights, tried to cover it, and waddled to the front door. (I think I’d even been given a cigarette as a prop, and in my haste I’d lit it to look more grown-up.)

My final words had been, “Well, toodles,” and I actually said that to Granny, remembering it from a movie somewhere, and skipped to the car.

Granny didn’t see Dad driving the car. I found out later that she told my step-mom that her home health nurse was the most quare lady she’d ever met.

We laughed all the way back to the house. Dad took the cigarette away. I was a 10-year-old and had survived an impersonation, a mission. I was too young to be THAT embarrassed. But looking back on it now…I think it takes the cake for most embarrassed I’ve ever been in my 30 years on this planet.

(And hey, for those that knew me in high school, it wasn’t the only time I had to wear something contrary for initiation’s sake.)

Life is too short to be taken too seriously. What’s your MOST embarrassing moment to-date? We all need a laugh every once in a while.

I can safely say I’ve worn men’s clothes ever since. And, I hope to for many more years to come.