Loose Lips Sink Ships: The Best ‘I Shouldn’t Have Said That’ Stories

From announcing pregnancies to her fiance that is supposed to be a total surprise, to letting it slip to grandma that grandpa is getting married soon, people share the worst thing they let slip in a conversation. 

[Source can be found at the end of the article]

I was at my uncle's funeral and my cousin was having a hard time accepting his dad is really gone. He was asking if it was an early April's Fool prank the day before, and that day, he grabbed me, pointed at the corpse, and went, "It doesn't even look like him! He looks different! Maybe it's not even him! Don't you think he looks different?"

I'm awkward enough already in most normal situations, and my mind just went blank at this point. The first reply I blurted out was, "That's probably because he's decomposing. That's why he's kinda bloated right now.


Once when I was having "the talk" with a soon to be ex, I dropped a bomb that immediately made me cringe: "I liked you before I got to know you."

A friend heard this story and says "aww, that's cute. You liked her even before you knew her that well." Nope, it was that I stopped liking her after getting to know her. The soon to be ex fully understood the statement upon delivery.


As part of my job I go to different offices in my company and speak about various work-related topics. I am also a member of AA. At a work meeting, where I knew perhaps 5 of the 100 attendees, I stood up and introduced myself saying"Hi everybody, I'm (name) and I'm an alcoholic.


Way back when, I was dating this girl. I was over at her place waiting for her so we could go out on a date. While I was waiting there her roommate came out of the shower completely naked and walked into her room.

Later that evening for some unknown reason I said "It is so nice to see that your roommate shaves down there.


My large uncle once wiped a turd on my bathroom wall. I think he just stood up and turned and accidentally got it on the wall (small bathroom) but who knows.

Any who, his kids came over a week or two later after having been estranged from us for years. Trying to lighten the awkward mood, I told the story about my uncle wiping poop on the wall, how weird and gross, like who does that? Completely forgetting the relationship between my UNCLE AND COUSINS. My cousin just goes ... my dad? wiped poop on the wall?

Couldn't recover so I just left the room for a while.


So, one of the worst things you can do in basic training is call a female instructor "sir," for obvious reasons. There were plenty who did this and were subsequently reamed. Well, I took it a step further, and called my male instructor "ma'am." "...Did you seriously just call me ma'am?" Fortunately for me, I think he got more confused than anything and we had things to do so there wasn't time to make my day hell.


I was having dinner with my parents and younger sister when I let it slip that Santa wasn't real. I honestly have no idea what I said or implied, but I will always remember the stares that could melt a thousand candles coming from my parents' eyes when I looked up from my green beans. And then my sister ran from the room, crying.


I got tricked into admitting to one of my best friend's very recent ex that he had cheated on her.

I wouldn't have been talking to her at all, but she had a very extreme reaction to the break up. She locked herself in their apartment and had been threatening to kill herself.

At one point, she said 'You know he cheated on me, right?'

'Uh, I guess.'

'So he did!'


A guy I worked with for a couple years older brother killed himself. Fast forward a month and he comes to visit the restaurant we worked at together and somebody jokes, who orders a non-alcoholic beer? what does stupid me say? "I would rather kill myself than drink a non-alcoholic beer."

Instant shame, regret, horror, you name it. I've never felt so terrible saying anything in my life.


Happened first week of college freshman year, in the dorms. Was chatting up this super cute girl with a couple of my new found friends. I mention I had always wanted to play drums, and the girl said she could let me borrow her brothers. Wow! Okay cool. Conversation keeps going, and something else, like some mics, and again her brother had one I could borrow/have. And then a THIRD thing comes up that was her brothers that I could have - so me, being me, said Geeze, youre giving all your brothers stuff away - Did he die???! HaHahah!!

Yep. He did.


Long story short. My best friend was engaged to a girl that I had slept with in the past. I was 18 at the time. We were in our 20s when they were engaged. I had no idea it was her. Keep in mind, her, him, my wife, and myself hung out all the time. He was/is my best friend. One night at dinner we were talking about where we all used to work. 

"Wait. You worked there? I worked in the building right next to it..." "When?... oh wow, so you worked there when I worked there... I once hooked up with a girl named name from there..." 

Then it all flooded in... embarrassing. They got over it, but she ended up leaving him anyway over her being stupid.


My grandparents separated before I was born (I'm 23 now) and when I was 6 or 7 my grandfather was getting married and I was to be the flower girl. Well, no one told my grandma wasn't supposed to know. So one day my family was at her house along with my aunt and uncle. And I mentioned how I couldn't wait to wear a pretty dress for the wedding. My grandma asked who was getting married. "GRAMPY IS!!" I exclaimed. And that's how she found out. Oops.


My best friend and I were talking while watching my kids play outside. I didn't realize they had come up to ask a question and we were talking about some not so good stuff that happened to us in Iraq and he said, "what about the dude you beat to death?" and I said, "it's a lot different than shooting someone." My 12-year-old said, "you've killed someone?" And my oldest smacked him in the arm and said, "at least two. Pay attention."

That was a really awkward conversation to have with them. I never planned on telling them what I did in the Army. They knew I fought in the war but didn't know any specifics.

Good news out of it though now neither of them wants to join.

(For context I'm a disabled combat veteran).


Back story: my best friend and I made out once. We realized it made things awkward and never spoke about it again.

Fast forward to this last year. I just moved in with my boyfriend and asked if we could have a small house warming party.

My boyfriend asked who I wanted to have over and I said my best friend Mike.

Boyfriend: Who is Mike? 

Me: My best friend from high school 

Boyfriend: ohhhh your best friend you made out with! 


Boyfriend: I was just kidding...

Hes very sarcastic and loves giving me a hard time about virtually anything, but I couldnt believe I let that one slip. It wasnt that bad, but it was pretty embarrassing to say the least.


I asked the wife during an intimate moment if she remembered the lap dance she gave me to a song that came on Spotify, then went on to describe the lingerie she was wearing and the way her perfume smelled. After getting an I should murder you and bury your bones in the garden stare down I realized that it was not my wife in this memory and my night was ruined.


I was on the phone with a customer. We were trying to determine if I had these pool floats in stock. They came in several different shapes and colors. Finally, I get an answer over the walkie. It's a busy day, and I'm multitasking between the phone, another customer waiting to speak to me, and ten thousand other things that need to get done, so I blurt out my reply.

"Hello, Sir? Yes, we have two left. One in the pink, and one in the brown." Then it hit me. Did I just say "one in the pink?" There was a moment of pause for each of us, but to our credit, we both recovered quickly and went about our day.


At a wedding, I met some guy back at the hotel that was a cousin of the bride, and I was on the grooms side. We were in the elevator when I started to talk about how I was banging the bride's sister a while back. As soon as I said it, I realized that the sister was also the guys cousin. I wasnt about to talk myself out of this one so as soon as the elevator doors opened I was out of there.


One time I was talking to my friend and her boyfriend (who was recovering from heroine use/abuse) and I was telling them how great the movie Oslo, August 31st is. They asked me what its about and I said oh yeah its about this heroine addict... I realized as the words slipped out of my mouth that I shouldnt have mentioned it. They asked me how it ended and I told them he died…


We were at a party after a university music department concert.

I was standing behind a tenor voice major at the bar when he asked the bartender for a soda. The bartender pulled the tab and was about to pour it into a glass when the student said emphatically (for all nearby to hear), "I prefer to take it in the can."

At which point I said, "I'm sure not many will be surprised to learn of your preference."


Not me, but a girl I was dating once had told me she lost her virginity to me. Then, a few months later, we were hanging out with one of her friends and she told a story about a guy who she had slept with and then told her he had had better. So she was either A. Cheating on me, B. Lied about losing her virginity, or C. Making stuff up. She immediately realized what she had said and after a long while she apologized and admitted to cheating on me.


2 years ago, I was talking in a group with basically the girl of my dreams. And my buddy, who is a football player, started talking about his weight and asked how much us guys weighed. And I'm a cross country runner so I'm fairly skinny. I was like "Oh I'm really light, like 115lbs, I wouldn't be suprised if [girl of my dreams] weighs more than me."

In my mind, I was thinking that since she was the next smallest person there, I would compare myself to her, because we were both light weight. But how it came out to her was, I called her fat straight to her face.


About six months ago my mother said that my cousin's parents where going to get a divorce but not to tell anyone. I forgot about it and on thanksgiving dinner last weekend someone else said it was weird how much the aforementioned parents where fighting. I than said "They are getting a divorce after all." The room when silent and my mom just glared at me. The worst part was that that thanksgiving was the first time I was seated at the adult table and it was a test run. Now I have to eat Christmas dinner at the kids table.


Growing up, the running joke in my family was that every time my grandma spent a good amount of money on something, it'd give my grandpa a heart attack. Rewind to 3 years ago, when my grandpa died of a massive heart attack. A few weeks later when I'd flown in for the wake, my grandma mentioned having bought something expensive (a bracelet or something) and I just blurted out "Jesus grandma, Grandpa'd have a heart attack."

Never have I felt so terrible or awkward - luckily my grandma is a hard lady and just smiled at me, knowing it was just a joke.


Years ago a lady at work whose husband had been super sick and on life support for months finally died, and a few weeks later, she was back to work.

I was the Safety Director and her department was having issues with a very old forklift. Me and my assistant were talking to her and she was telling me how it kept needing to be fixed and was always breaking down, and I said "Yea we're just keeping it in life support and it's time to let it die."

I swear at the time I was just using an analogy, about 10 minutes later my assistant was like "Oh my GOD! DUDE! why?!?!".....

I then realized the connection and went back to apologise. She was of course crying since our conversation.


I let it slip that my dad had cheated on my mom multuple times with two different women, one woman who she was close with. And that myself and my younger sister were present during some of these occasions.

I was too young to understand what had happened. I just remember the look on her face when I told her. My dad later blamed him getting caught on me and called me every other name in the book.

My parents got divorced. I'm not on speaking terms with my father.


I accidentally told my best friend that his fiance was pregnant. I'd heard through mutual friends and no one told me that it was a secret or surprise. She'd even posted it on Facebook!!

Come to find out, he'd deleted his Facebook months before in protest of something stupid and hadn't found out yet.

"Hey!! Oh my god I can't believe you're gonna be a father!! Have you started freaking out yet??"

Yes he did freak out. Right then. Loudly.

In the middle of an olive garden...


I noticed an attractive woman at my gym one year but never thought much about it after that moment as she was much shorter and I tend to prefer taller women. A few months later, we matched on Tinder and I figured I'd at least give it a try. Eventually we caught each other at the gym and over the span of a few weeks we chatted pretty heavy at the gym, texted a lot and even went on a few dates. While stretching together at the gym one day, she asked me why I wasn't making a move. For some reason, I blurted out I wasn't into short girls. The look on her face made me realize I was probably the biggest jerk she's ever dated. I felt so horrible as she was an amazing woman. She never talked to me much after that and I learned a lot about myself that day.


One of my friends had recently broken up with her boyfriend. He was a very big guy. Very. Big.

Anyway, she was showing me old pictures of the two of them from high school. In these pictures, they were both dramatically skinnier. Almost unrecognizable.

Immediately, upon seeing the photos I said, " Wow, you both used to be really skinny!" Not realizing it was an insult, until she replied..."Thanks" very sarcastically. Oops.



When in doubt.... be a Karen! LOL

We've all seen them and at times we may have been one A KAREN! You know who that is.... a difficult person, that's describing it politely. Karen's make scenes and do all that is necessary to get anything and everything their way. Working in any form of a service job, Karens are your worst nightmare.

Redditor u/externalodyssey wanted to hear from everybody about their Karen encounters by asking.... Managers of Reddit - what is a Karen experience like ? What was you worst experience ?

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