Hilariously awkward conversations you overhear are a gift sent from the comedy gods, and these 12 examples are hysterical, sweet, and everything in between.
Sit back, relax and enjoy the funny!
12. Totally Real Call
I was on the train heading to work when a middle-aged guy wearing a suit starts talking on the phone to someone who was supposedly a ‘business partner.’
After a bit of smalltalk, he started talking with a loud, obnoxious voice telling this man that, “I think we can both make around 3 million on this deal. But that’s nothing compared to the contract I signed last month! Hah!” Or “the wife wanted new tint on our BMW so that’s at the workshop, and I had to take the train.”
The train was moderately full, so obviously he was getting a few looks from other passengers. He seemed to thoroughly enjoy being the centre of attention.
And then, at the most hilarious moment possible, his phone actually started to ring. He quickly declined the call and starting looking around to see if anyone was looking, which we all were. You could see the whole world collapse in front of him.
It’s safe to say that the train burst out with laughter, and this man’s face went more red than I thought humanly possible.
A few people made little comments as he hurried off at the next stop, but my personal favorite was from a young guy who shouted “best of luck with the deal! And I hope your wife enjoys the new tint!”
I was standing in line at the store when I heard two old ladies talking.
“I bet I’m older than you.”
“Yeah? I just had my 75th birthday.”
The first woman grinned.
“I’m 89 years old.”
“Wow! You don’t look a day over 70.”
“I color my hair,” she said, pointing to her roots.
I smiled. I can’t wait for the day when the phrase “you don’t look a day over 70” is a compliment.
10. Mighty Pussy
I was standing behind a lady in Starbucks, in LA. She orders unnecessarily complex coffee with whipped cream and a bunch of bagel bites. Then she asks for a small cup of milk. “”Make sure it’s whole milk. Not 2%.”
“Ok, sure. Would you like that in your drink, instead of the soy milk?”
“No, mine has to have soy. This needs to be in a cup. A small cup.”
“What name should I put on that?”
“‘Susan’ on the coffee and ‘Mighty Pussy’ on the milk.”
“Mighty Pussy. That’s who the milk is for.”
I start laughing.
And then Mighty Pussy stuck her head out of this lady’s purse-closet, and meowed loudly.
And they did announce Mighty Pussy when the order was ready. I laughed so hard I snorted. Everyone was so serious. This whole scene still cracks me up.
9. Get Some Sleep Officer…
Very early one morning, I was third in line at the counter of a deli/convenience store just outside of Harvard Square, right behind a fairly tall, imposing policeman.
The person at the front of the line was taking a long time, and the policeman obviously zoned out.
Finally, the first person finished and stepped aside.
The policeman stepped forward, and firmly demanded of the clerk, “License and registration, please! …Oh, sorry, sorry. A pack of Winstons, please.”
8. Lost in Translation
Overheard on a train between two apparent friends in their teens, a girl and a boy.
The girl spoke American English, the boy accented English, and she was helping him practice.
They closed their book and were quiet for awhile when the boy says to the girl, “I am boring.”
In an exasperated voice she replies, “NO Bill, it’s BORED, you are BORED, not borING. This is why no one wants to hang out with you, you are always telling them you are boring!”
It was on the bus. From the Valley to Los Angeles. A guy and his girlfriend, I assume. Here is the conversation as close as I can remember. It started as we rolled onto the freeway to go over Cahuenga Pass. She starts it.
“Well, then I started pulling on it. And it just kept coming and coming, so I kept pulling, and wrapping it around my fingers.”
“Wow! How long was it?”
“I don’t know… a few feet, maybe… ten, twenty? And I tried to break it, you know, snap it off but it was just too strong. So I kept pulling and winding. I knew I was unraveling something but couldn’t figure out what! So I just kept on pulling.”
“Was it from your bra?”
“Nope, it was at my waist. I’m pretty sure it was from the bottom part of my clothing. Pretty soon I had a whole handful of it and I was wadding it into a ball and wrapping that.”
“Had to be your panties! I’ll bet it was your panties.”
“No, I already told you I was certain it wasn’t them. Wrong color. Anyway, so this went on and on and I was sure my parents would notice. But you know them. Oblivious.”
By this time we had left the freeway and gotten into L.A. I was transfixed!
People started getting on and off as the bus went down Broadway.
“Anyway this big ball was in my left hand and I was using my right hand to wind it. Oh, here’s our stop.”
“Wow, so what was it?”
“Well it turned out that I had completely unraveled my-”
At that point they had arisen and stepped off the bus! As the bus doors closed, one lone voice could be heard as it pulled away…
I never DID find out what she had completely unraveled!
6. The Scottish Way
Two old ladies were sitting on the bus in front of me, in Edinburgh.
One had just come back from a holiday to the US – or maybe Canada, I forget which.
She spent about five minutes expounding on how much better the service over there was, how friendly the shop staff were, how helpful everyone was, how everyone wished you a nice day.
This was followed by a thoughtful silence and then she added, “It gets on yer nerves.”