Gina Heslop
What do a young businessman and a pom-pom hat have in common? Both are featured in ordinary life situations that took unexpected and hilarious turns.
These are some of the funniest and most awkward stories shared by people online.
- When I was a little kid, my parents were giving me a bath. They both left the room for just a minute, and I heard the ice cream truck. So, I ran down the street after it, completely naked, with bubbles all over me.
- I once started a flower-selling business as a kid. I would go into someone’s yard, pick all their flowers, and then ring their doorbell to ask if they wanted to buy the flowers I had just picked. My business got shut down very quickly.
- This happened to my boyfriend. He was picking me up after work in the winter. We were both in a bad mood. When I got into the car, I noticed something strange about his hat; it was sitting too high on his head. I told him, “I think your hat is inside out.” It was a pom-pom hat, and we laughed about it all the way home and couldn’t stop.
- I often find myself in awkward situations, but one really stands out. Several years ago, I was selling a book online. A buyer called, and I was sure it was a woman named Ann. When I went to our meeting place, I saw no women, only a short guy looking at me. I called, “Hi, Ann. I’m here. Where are you?” The guy waved and, in a female voice, said, “You just walked past me.” I blushed, handed over the book, took the money, and walked away laughing. I couldn’t stop laughing all day.
- When I worked as a secretary, my boss told me that a guy named Mark would be coming in. Later, a guy showed up asking for my boss. I said, “He’s away, but he’ll be back soon. Are you Mark?” He replied, “No. I’m Lucy.”
- A friend of mine didn’t want to go to school, so he would go up one floor in their apartment building and wait for his mother to leave for work, then go back home. Once, he was so lazy he just hid in the wardrobe. When his mother opened it to get a coat, he scared her terribly.
- I was waiting at a traffic light when a local dog, known as “Dog,” came and stood next to me. The dog only crosses the road with people. While waiting, I was on my phone. When the light turned green, I said, “Let’s go, Dog,” and looked behind me. The dog was gone, but a guy was giving me an angry look. I didn’t explain myself, hoping he had seen the dog earlier.
- I once dated a girl and, after going to the theater together, her parents let me stay at their place in another room. I waited until I thought her parents were asleep and snuck into her room. Just as I was about to get into her bed, I heard her father’s voice say, “Jack, Ann is in a different room.”
