What is the most awkward situation you have experienced? Why was it so awkward?


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Most Helpful Guy

  • An acquaintance of mine named Bill had been dating a girl Rebecca for nearly six years, and when I saw him and some other people out at a restaurant, they asked me if I had heard what had happened to the two of them. Now I've known a lot of people in my circle of friends and acquaintances who either are married or just got engaged, and without thinking first, I blurted out "Congratulations!". This was a huge miscalculation on my part though, because the news wasn't that they were engaged, but rather that they broke up.

    I quickly apologized and explained why I had said what I did, but Bill has such a good sense of humor that he laughed about it over a round of beer (which I insisted on paying for, lol). It has now become known in our group of friends as the "congratulations" story, and they won't let me ever live it down. 8-)

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What Girls Said 2

  • Most awkward? I was out with a bunch of friends two years ago and went to a club. I had run into some friends that I hadn't seen in a few years. I then blurted out, "Congratulations that baby bump is looking so adorable." to a former co-workers wife. She froze and said, "I'm not pregnant." She then glared at her husband and said, "You see! I'm ugly and fat!" I have never felt so stupid in my entire life. I apologized and high tailed it out of there.

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  • A few summers ago, I was heading to the subway station. I got there right before the door was about to close, and I ran for it. It had been raining and I was wearing flip-flops, the platform was very slippery, and as I reached for the closing doors, I slipped and fell face down on the train, half my body was inside and the other half was outside the closing doors. It was awkward, embarrassing, and intensely painful.

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What Guys Said 1

  • In a room with my girlfriends who family and I was ment to say something was getting on my nerves and I said nob instead! OMG her nan just looked straight at me along with the rest of her family! even the baby!

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