14 Hilarious Stories About Really Awkward Situations

11 months ago

What do a young businessman and a pop pom hat have in common? These are some ordinary life situations that didn’t go as planned. These stories will definitely make you laugh.

Our readers and internet users shared their awkward stories. We at Bright Side love this humor and we’ve compiled the most interesting stories we could find.

  • My parents were giving me a bath, they both left the room for some reason for only a minute, and apparently, I heard the ice cream truck and ran down the street after it naked with a trail of bubbles. © pelt / Reddit

  • I started a flower-selling business. I would go into someone’s yard and pick every flower. I would then ring their doorbell and ask them if they wanted to buy any of the flowers that I had picked. That business was shut down pretty quick. © RylieSmash516 / Reddit

  • This is not a story about me. My boyfriend was picking me up after work, it was in winter, and it was cold. We both were in a bad mood. I got into the car and started talking and I saw that something was wrong. His hat looked funny, it was too high. I said, "I think your hat is inside out. By the way, it was a pom-pom hat. We were laughing all the way home and couldn’t stop.

  • I get into awkward situations all the time. I don’t even worry about them anymore, but I remember one situation well. Several years ago, I was selling a book online. A buyer called me and I was sure it was a woman. I even thought she said her name was Ann. So, I go to the place we agreed to meet and I saw no women there. There was a short guy that was looking at me. I called the phone number, “Hi, Ann. I’m here. Where are you?” And this guy waved at me and said in a female voice, “You just walked past me.” I was blushing, took the money, gave him the book, and walked away laughing. I couldn’t stop all day. © Deleted User / AdMe

  • I worked as a secretary. My boss went away and warned me that a guy named Mark was supposed to come. Sometime later, a guy comes and asks for my boss. I said, “He’s away, but he’ll be back soon. Are you Mark?” The reply was, “No. I’m Lucy.” © Alisa Selezneva / AdMe

  • My friend, when he didn’t want to go to school, went one floor above their apartment, waited for his mother to go to work, and then went back home. But once, he was so lazy that he just hid in the wardrobe and scared his mother terribly when she opened the wardrobe door to get a coat. © Andrushka1982 / Pikabu

  • I was waiting for the traffic light to turn green. A local dog (smart boy) came to me. He only crosses the road with people. Nobody knows the name of the dog, so everyone just calls him Dog. While I was waiting for the green light, I was on my phone. 2 minutes later, I saw the green light and said, “Let’s go, Dog.” I looked behind me and there was no dog. But there was a guy that gave me an angry look. I didn’t explain myself and I hope he’d seen the dog. © Panteleev / Pikabu

  • I remember I dated a girl. And once, after we went to the theater together, her parents let me stay at their place in another room. I waited for the moment when I thought her parents fell asleep and snuck into her room. As soon as I was going to get into her bed, I heard, her father’s voice, “Jack, Ann is in a different room.” © Alex / Facebook

  • When we were young, we had nicknames for each other in our family. My husband was a squirrel because he would bring a lot of stuff home, I was a raccoon because I washed everything, and my daughter was a hamster because she had big cheeks. We went camping and stayed in a tent. My daughter came up to a woman from a nearby tent and told her, “My father is a squirrel, and my mom is a raccoon.” The woman was gone the next morning. © E.L. / AdMe

  • I was at a store and the girl was preparing my receipt. I noticed that she had a funny last name on her badge. I wanted to take a photo, but forgot to turn the sound off. When the girl heard the sound and realized what I was trying to do, I was terribly embarrassed. © “Podslushano” / Ideer

  • A taxi driver forgot me. I called a taxi and I had a big bag with me. So, I put the bag on the back seat from one side and went to get into the car from the other side. While I was walking to the door, the car drove away. Fortunately, I had my phone with me, so I called the guy. He was shocked when he saw the call from me because he thought I was in the back seat. © Tanya Cheys / Facebook

  • My 3-year-old grandchild and I were going from one room to the other through a double-door. Usually, one door is open and the other one is closed. The grandchild runs to the door and opens the second door. I asked him why he did it and he said that I was too fat to squeeze in. I guess it’s time to lose some weight. © DedX5 / Pikabu

  • About 7 years ago, when I just started driving, I wanted to go to the mall with my friends. In the parking lot, I hit someone’s car. I wasn’t really sure if I scratched it or if there was still some hope. The 4 of us got out of the car and we decided to lift the car to see if there was a scratch. 4 girls trying to lift a car and 2 guys not far from us laughing. So, I asked the guys to drive my car carefully because I was scared to hit another car. One of the guys said, “No problem.” I wanted to give him my keys but he said, “I have my own keys. You hit my car.” I apologized, and he was very nice and helped me solve the problem. © “Podslushano” / Ideer

What awkward but funny situations have you experienced? Share them in the comment section below!


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Oh man these remind me of myself... I am a bit clumsy and get into akward situations all the time


I can see myself getting into the online book one... at least I wouldn't be ashamed of this situation I would just laugh


A few months ago my almost 10 year old grandson was at my place with his almost 8 year old brother. Eldest had called a friend who played the same phone game as him and I really thought he was talking to a girl. For hours. I asked the youngest who he was talking to and apparently it was his friend zach. I said are you sure it's not a girl? Nope. Even asked my daughter and she said the same thing, zach is a boy same age as my grandson.


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