Hilariously awkward conversations you overhear are a gift sent from the comedy gods, and these 12 examples we curated from Quora are hilarious, 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!”

11. Awwwww

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.”

“Im sorry?”

“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!”

7. Unraveled

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.”

5. Bad Sandwich

I was visiting Colorado for a 2 week backpacking trip when I heard this. It all happened in a Denver airport bathroom…

A man answered his phone call while taking a pee. “Hey, babe!” he exclaimed. “Where am I? Uhm, Colorado…” he said dreadfully. You can just see the worried look on his face. It was so intense everyone stopped their business but him to watch this phone call.

He continued to talk with his girlfriend about how he was here for business (funny, he looked like a stoned high school senior). He was definitely in Colorado to get high and other stuff that definitely wasn’t “business.”

The man looked at all the men and boys embarrassingly around him before answering whatever the girl asked next.

“Yah, babe. When I see you, expect the biggest, baddest, penis sandwich ever.”

The whole bathroom erupted in laughter. I myself was almost on the floor. Once we started laughing, I am guessing his girlfriend heard us and assumed he was at a party and immediately hung up.

The man was out of there before we could say “sorry.”

4. Cold Blooded

Out at a bar, table of four girls together behind me.

Two guys walk up to them, “Hey are these seats free?”

Girls: *enthusiastically* “Yeah, definitely!”

Guys: “Oh awesome!” *pick up the two seats and walk away*

Living in the south, it was the coldest thing I’ve seen all winter.

3. Boning

I am in the elevator with three co-workers, all of whom are artists. We are going to lunch and discussing what is on our plates for the day.

Artist 1: “If you need help skinning the cat let me know. I’ve got some free time. Waiting for Artist 2 to finish boning the female.”

Artist 2: “It’s not my fault boning her takes so long!”

Artist 3: “I should finish skinning the cat before tonight, but thanks.”

I was trying so hard not to laugh at the two lawyer types who were in the elevator with us. Their look was priceless, and I burst out laughing when they sprinted out.

For the puzzled:

Skinning means adding the texture to a 3D model. So he had to texture the (big) cat model.

Boning means adding the bones (or skeleton) to a 3D model. We had one female playable character who needed a different skeleton so she would move correctly.

2. Little Chicken

I am French and my girlfriend is Indonesian. We communicate between ourselves in English, because my girlfriend doesn’t speak a word of French.

We went to my grandma’s house in the countryside of France to pay her a visit, and on this side of my family, no one speaks a word of English, even the basics such as thank you etc…

My girlfriend was using this technique that consists of repeating the last words of the sentence that has been said to you when you don’t understand. Of course you won’t go too far in the conversation with repeating the last few words, especially when you have no idea what it means, but you can pretend that you get the message.

I was trying to help both sides most of the time, but once in a while, I won’t lie, it was super fun to just sit and watch and see how it went. One moment was particularly funny. I was in the kitchen, listening to my grandma talk to my girl.

My grandma, bringing a chicken while looking at my girlfriend: “Et voilà un petit poulet.” (Here it is – a little chicken.)

My girlfriend, with no idea of what have just been said: “Petit poulet?”

My grandma, smiling: Petit poulet.

My girlfriend, super enthusiastic: Petit poulet!

My grandma, thrilled: Petit poulet!

Then everyone laughed with no idea of why this conversation even happened!

When we left, my girlfriend cried a little because she found my grandma adorable, and my grandma told me that my girlfriend was great.

From the few days we spent there, this was probably the deepest conversation they had without me translating.

1. New Tricks

I was in a local grocery store that caters to Latin customers.

Although I’m fluent in Spanish, I stand out. Like I don’t belong there. But it’s in my neighborhood. The closest market. That’s where I frequently shop. My pantry is packed with products with labels written in Spanish.

While in the housewares aisle one day, two sisters were looking at a huge toilet plunger and were arguing whether their puppy could possibly swallow it or not!

They argued if it was cheaper than a regular dog toy, probably made out of the same super-strength rubber, and wondered at the same time, if their puppy could get it down his throat and choke on it.

What? Seriously? It was huge!

Have you seen how BIG those industrial-strength toilet plungers are? They were barely able to get their hands around it. I wondered just how big their puppy was, to be able to swallow that thing.

One sister went on to refer to the time “Francisco” swallowed a beer can, whole! They laughed at this. The other, laughed and said that was nothing, “María” could swallow a baseball bat and a beer can simultaneously.

They belly laughed. So did I. I couldn’t help it.

The sisters swiveled their heads in my direction, as they suddenly realized I understood every single word they were saying. They explained their puppy was an exceptionally large 1 year-old Rottweiler, and had a chewing problem.

They explained that they had read about the Kong toys everybody was buying to curb chewing problems in dogs, and pointed out that for 1/4 of the price (and the same industrial strength rubber) they could devise their own version of the “Kong” with the plunger.

When they wondered if the puppy could choke on it, they meant, could he get his nose stuck inside with the treats, not literally that he might swallow it. That part was a joke.

They said they would trim off the inner sleeve, so that the suction would be broken, and of course, they would also remove the plunger stick.

I bought two plungers for my own dog, and cut the inner sleeve out, sanding the edges smooth. I removed the stick and filled the hole with peanut butter and stuck it in the freezer to create a solid “plug.”

When it had frozen solid, I filled it again with water, and refroze my homemade “Kong toys” and made frozen summer “pupsicles” for the upcoming heatwave.

I had backups to keep my dog cool.

Kong toys retail for $17 in my area. The plungers cost $3.69 each. I saved a great deal of money having eavesdropped on that conversation that day.

…And they say “you can’t teach an old dog new tricks!”