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-)1