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Your most awkward moment

A long time ago I got a new boss who had been promoted from among our ranks but in a different division. He was a guy I had met and seen but didn’t know. So he picks me up at the hotel we drive to a restaurant and park. We both get out and had walked twenty feet when I notice he is limping.

“Hey Dave, what did you do - twist your ankle?”

Long pause.

“Actually I have an artificial leg.”

Another INTERMINABLE long pause.

“I was eighteen at the time - went down on my motorcycle - and .... come to think of it ... yes, now that your bring it up... I have been living longer without my leg than with it."

S-I-L-E-N-C-E ...
 
That's not too awkward. It was probably way more uncomfortable for you than it was for him. He's already living without the leg, so explaining what happened isn't a big deal.
 
I have many. :blushing: In my defence I am not a morning person (don't get enough sleep). Here is one:

After getting to work in the morning, my girlfriend at that time called me over the phone and told me how much she loved and missed me....so I ended the conversation with, "Love you too baby." With a smile on my face I got up to get some coffee and ran into my co-worker David.

David: Good morning Noah!
Me: Good morning baby.

FUUUUUUUUUUUUUUDGGGGE!
 
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I have many. :blushing: In my defence I am not a morning person (don't get enough sleep). Here is one:

After getting to work in the morning, my girlfriend at that time called me over the phone and told me how much she loved and missed me....so I ended the conversation with, "Love you too baby." With a smile on my face I got up to get some coffee and ran into my co-worker David.

David: Good morning Noah!
Me: Good morning baby.

FUUUUUUUUUUUUUUDGGGGE!

Wasn't it popular at one point for a man to call another man "baby"? Like in an urban/ghetto slang sort of way. "Hey Baby, what's happenin'?"
 
Been way to many times I've been on the phone with some one and started to say "I love you" as we said goodbye.

So far, I haven't said it, but one of these days....
 
Try this one on. Years ago I was attending a semi-annual sales meeting. There were about 25 in a small meeting room all of us sitting in a horse shoe shaped set up. Most of us only knew each other in a very general way. Just as we had been dismissed for a short break I turned to a young lady in her mid-twenties whose name tag was different from the last sales meeting.

As everyone was rising from their chairs I said in a loud voice to her, “Say, congratulations!”

She paused and with a confused look said, “For what?”

Stating the obvious I said, “Hey, you’re married - you have a new name!"

With that the room went deathly silent. Somewhere a guy snickered.

She replied, “Oh, actually I am now divorced and I took back my maiden name."

That is when for the first time I looked at her ring finger, her bare ring finger...

And yes, later I got to listen to the guys reliving it over and over and over again.
 
My friend had a pretty similar thing happen. He works at an electronics store, and they're supposed to walk around asking people if they need a hand. On one occasion, he said it to a guy who turned around, revealing that he was missing an arm.
 
Gender confusion is always awkward. I was at Wal-Mart buying a phone service card for my Straight Talk phone, and the young man ringing up in the electronics store was pretty effeminate -- long way hair, soft voice, wearing sort of like a blouse type shirt on. After he was done with me, a woman asked him: "Ma'am, can you please help me with the cameras? I don't know which one to buy." He didn't seem offended. He might actually be trying to be more female like.
 
Gender confusion is always awkward. I was at Wal-Mart buying a phone service card for my Straight Talk phone, and the young man ringing up in the electronics store was pretty effeminate -- long way hair, soft voice, wearing sort of like a blouse type shirt on. After he was done with me, a woman asked him: "Ma'am, can you please help me with the cameras? I don't know which one to buy." He didn't seem offended. He might actually be trying to be more female like.

Had the same thing happen.....
I was substitute teaching at a middle school once and during one of the periods, I had a student who had long curly hair with neon colored bracelets on. I passed out some worksheets and told one of the students to pass the paper back to her. Everyone, just stopped for a second and starting laughing. The student I was referring to was male and laughed along with everyone else. I apologized to him and he said, "It's okay. I get it all the time."
 
Try this one on. Years ago I was attending a semi-annual sales meeting. There were about 25 in a small meeting room all of us sitting in a horse shoe shaped set up. Most of us only knew each other in a very general way. Just as we had been dismissed for a short break I turned to a young lady in her mid-twenties whose name tag was different from the last sales meeting.

As everyone was rising from their chairs I said in a loud voice to her, “Say, congratulations!”

She paused and with a confused look said, “For what?”

Stating the obvious I said, “Hey, you’re married - you have a new name!"

With that the room went deathly silent. Somewhere a guy snickered.

She replied, “Oh, actually I am now divorced and I took back my maiden name."

That is when for the first time I looked at her ring finger, her bare ring finger...

And yes, later I got to listen to the guys reliving it over and over and over again.

Change 'divorced' to 'widowed', & then you have a scenario I witnessed. Now THAT'S awkward.
 
Here is one that happened to a pastor that I know.

The congregation was large enough that he didn’t always see everyone very often. So he saw a woman who clearly had a bulge going on. As the rest of us have learned he did not dare say anything unless he knew for sure a lady was expecting.

With the confidence that only comes from certain knowledge and with a happy face he approached her and said, “Congratulations on your big news!”

She looked startled and glancing down answered by saying, “Oh, I had my baby four months ago..."
 
This one didn't happen to me but i witnessed it:

I was at Walmart one day looking in the sporting goods aisle and there was a guy there that had a perm in his hair and was bent over looking at something on the bottom shelf and a Wally world employee came up and asked "can I help you find something maam". I had to walk away very quickly to keep from busting out laughing.
 
Not mine, but I witnessed it. When I was a kid we went to church with some regularity. In our specific religion, members often stood up to speak to the congregation. An elderly member stood up to share a story about a trip involving her family and their new boat. She said that her son had gotten a new POONTANG boat obviously meaning pontoon. You could have heard a pin drop.

Jim
 
In college I was in an amusement park with my buddy and his family. At one point in the day, we got turned around, and as we were trying to find our bearings I referred to the situation as the blind leading the blind... yeah, his mom is blind. Awkward!
 
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