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


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.

  • 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.


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!