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awkward moments
collect the set!
by jason gilmore (@JasonGilmore77)

We all have them. Often. But don’t be ashamed. Collect the set and trade them like baseball cards or food recipes. They are the extreme moments of discomfort for you and others. Here are some of my truly awkward moments:

Awkward Moment #1, 460
Summer 1981, Toledo

My Aunt Pat was dating a man named Frank, who would later become my uncle. But at the time, they were just dating, and he was the only man I’d ever seen with my aunt. So she shows up with this other guy and she and the guy and my mom and dad were in our basement, drinking and talking and having a grand old time. I sat across the room, in front of my infamous blackboard, which I wrote on frequently. As they laughed and joked, I turned to them and yelled, “Aunt Pat! Look!” and pointed to the blackboard. On it, I had written in big letters,


As my aunt, mother and father gasped in horror and her unsuspecting date probably thought to himself, “Who the hell is Frank?” I smiled and finished the sentence:


Awkward Moment # 4, 745
Spring 1989, Silver Spring, MD

I was pretty nerdy in seventh grade, although you couldn’t have told me that then. On a class trip to our nation’s capitol, I decided that I wasn’t leaving without some fine filly’s digits. There was a pretty brunette clerk at our hotel that had been (I felt) extraordinarily friendly with me all week. It was time for me to close the deal. I had always been into older women, but had a hard time gauging the age difference between us.

So I approached her and noted the lovely beige dress that she wore that day.

“You look gorgeous,” I said, fully prepared for her to be overwhelmed by my charm. “That dress makes you look ten years younger!”

“I’m 19,” she said, with the severest frown. “Are you into nine year olds? I can't believe you're a pervert already.”

Awkward Moment # 5, 222
Winter 1992, Toledo

After basketball practice, I head over to the vending machine to buy a pop (now, thanks to seven years in California, I call them sodas) to drink while I wait for my parents to pick me up. My school was the elite of the elite, and a melting pot of sorts: rich white kids, kids whose doctor parents were from India, Korea, Turkey, etc. They hd everything, really, except more poor black kids like me. Anyway, as I made my way back to the main lobby, an elderly Arab couple approached, arguing about something. I paid them no attention.

“Excuse me,” said the man, “do you know where we can find my grandson Abdul? We came for Grandparents’ Day and we have misplaced him.”

My school was K-12, but small. Still, I didn’t know anyone named Abdul. Besides, Grandparents Day was more for the elementary school set, and as I was in the 10th grade, I could’ve cared less.

“No, I’m sorry. I don’t know your grandson,” I said, and began to walk away.

As I left, the woman spoke to her husband. “I don’t know why you asked him. He’s so much older than Abdul. How would he know?”

“He should know, he’s the janitor,” the man said. “The janitors know everything!”

Awkward Moment # 8, 784
Spring 2001, Beverly Hills, CA

One of my job responsibilities during my tour of duty at a TV movie production company that shall remain nameless was to drop off any check deposits at their bank in Beverly Hills. In front of the parking structure was a loud black man in a wheelchair who asked for money each day. Normally, we had cool correspondence, but this day, for some reason, I wasn’t sympathetic. Besides, I was short on change and wanted to get this done before the minimal time someone else left on my parking meter eroded.

“Hey young brotha,” he said, as with every time he saw me, “can you spare me a couple dollars?”

“Nah, man,” I said. “I’m too busy working.”

So I went up in the bank, dropped off the checks and got the receipt. I’m strolling back outside now, to run another errand up the street, when I see a cop standing by my car, writing a ticket.

“C’mon,” I said. “I’m right here!”

“Your meter just expired,” said the cop. “If you put in another quarter right now, I’ll let you slide.”

And wouldn’t you know I didn’t have any change that day. Desperate, I looked to my left and my right. And there I saw him, the homeless dude, smiling, with a big plastic cup full of change.

“Hey brotha,” I said. “Can you spare a quarter?”

“Nah, man. I’m too busy working,” was the last thing I heard, before he rolled his wheelchair down Canon Drive.


Jason Gilmore is a film director, screenwriter, novelist and unrepentant Detroit Pistons fan. Track him down on Facebook.

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sandra thompson
11.20.06 @ 7:28a

You have the coolest embarrassing moments of anybody I know or know of. I was gonna share mine but I seem to have repressed them all. I am OLD and tend to forget things but this is ridiculous.

tracey kelley
11.20.06 @ 5:36p

I was booed off stage at a concert that I was emceeing by an angry throng of college students.

I also got the hem of my dress stuck in the back of my pantyhose once. Fortunately, the only people I flashed my ass to were family members, but, you know, still.

Awkward moment #8,784? Wow, what a story.

kasandre kirby
11.25.06 @ 3:50p

WOW... that Beverly Hills joint is real shady. That makes me think twice about the times I pass folk up because "I'm too busy working," or getting where ever I have to be.

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