People Share Their Worst, ‘It Sounded Good In My Head’ Moment

Humans are social creatures, and with socialization comes wit and mental planning. We’re always trying to think of a new comeback, reference, or a joke to make the crowd laugh. Sadly, though, a lot of the stuff we come up with sounded good in our heads then when executed, whether we can’t correctly pronounce something or use the wrong words.

Usually, it ends up alright, but these people shared their stories on the horrible times they said something that sounded good in their head but made the situation they were in very awkward.

Although awkward for them, it’ll be hilarious for us who are reading, so scroll on down to read stories on how people said something that sounded great in their head but went badly.

Don’t forget to check the comment section below the article for more interesting stories!

#1 Things Not to Say to New Parents

My friend is holding his infant daughter.

In my head: “She’s so lucky to be born in our modern world, medicine is advancing so fast she may well see the cure to old age, practical immortality.”

Out of my mouth: “I wonder how long she’ll live?”

Nobody’s ever given me a dirtier look.


#2 How To Lose Your Babysitting Gig

What worked for me: My cousin was complaining about how his kids were basically balls of energy and that it would be nice to have a few hours of peace for a little while.

Me: “You should grab a couple of my muscle relaxers, crush them up, and put them in some hot cocoa for the kids. That should knock them out for a few hours. They’re pretty decent sedatives in light doses.”

Him: [blank stare] “Remind me never to let you babysit my kids…”


#3 He Really Got Himself Into Hot Water There

I was a waiter and had a table with an African-American family (I’m white). We had a great rapport. Then the son said something to which I responded: “Well that’s the pot calling the kettle (slight pause) hot.” They stared at me for a beat then started laughing hysterically.


#4 Clean Mouth But With A Dirty Mind

I was at a dentist appointment and the doctor and hygienist were both trying to look at my teeth. While they did this, I said: “I can only handle one person in my mouth at a time.”


#5 Sometimes Love Kills

My dad, mom and I were at a funeral for an older lady we’d known for years (I was probably about thirteen). Her son, who my parents had never met, was in the receiving line. When we got to him, my mom is talking about his mother and how much everyone loved her, etc. When we’re getting ready to walk away, my mother smiles at this guy, a little misty eyed, and says, “We just loved her to death.”

Fortunately (or unfortunately, depending on your perspective) for her, this guy was a fucking boss because, without skipping a beat, he deadpans it and says, “So, you’re the reason for all this.”

I swear to god my dad and I laughed the entire way home.


#6 PerHERPS He Shouldn’t Have Said That

“I’ve got the herps.” Is what I said to the entire group of high school students from my church.

What I MEANT was, “I have a combination of the hiccups and burps.” Which I had previously, to my own amusement called “hurps.”


#7 That’ll Make Thanksgiving Awkward

My boyfriend’s family went to dinner with my family, so his parents could meet mine. His family was kind of large. Both sets of parents were talking about the price of the restaurant we chose, and out of my dad’s mouth pops, “At least I only have to feed the skinny ones.” Dead silence, other than the sound of me shoveling a hole to hide in.


#8 Unintended Innuendo

It was raining. A classmate had forgotten her umbrella and was talking about how soaked she was.

My genius quip: “Oh don’t act like this is the first time you’ve ever been wet around me.”

It may have only been a few seconds, but the silence and staring at me that followed is burned in my mind forever.


#9 Lost in Translation

My brother-in-law, who is Indian, told one of my sisters that she looked very fat in her bridesmaid dress. To him it was a compliment, he was trying to say that the dress fit her well. To her, it was the most insulting thing anyone could ever say.


#10 The Flew Right Over His Head

I overheard this on a plane coming back from Iraq.

We had just landed in the United States and a guy leans over to a portly female soldier sitting next to him and says, “So how does it feel to go from a nine to a five?”


#11 That Didn’t Exactly MEAT Expectations

I told my ex-wife that she looked like Meat Loaf. It was the hair. She had just shaken her head, and her hair was glowing sort of shimmery-like.

Clearly, I am a moron, but in my defense, we were both very under the influence. She cried really hard.


#12 We All Use to Love Denny’s

My sister had just been dumped by her fiance. She was devastated. We were at Denny’s, where they use to eat a lot, and we were thinking about what to order. She said “You know what Bryan use to love?” meaning something he always ate there. Without skipping a beat, I said, “You?”

She cried.


#13 That Quickly Escalated

Once my wife asked what I thought was “Do you want a Twinkie?”

My response was “Heck no. I just ate.”

She cried and went back upstairs. Only for me to find out it was “Do you want a quickie.”

That was the worst trip back home on my lunch break ever.


#14 Brains Over Beauty

I told my wife “I didn’t marry you for your looks” when attempting to compliment her intelligence.


#15 Whoever Said Math Was Boring?

I was in a Computer Science class, and we were converting binary to decimal and vice versa. I asked the teacher “Can you do 69?” referring to converting 69 from decimal to binary. He and the rest of the class howled after he responded with “Yes I can.”


#16 Cutting Edge Customer Server

It was my first week working at a jewelry store. I’d been told by the manager to listen to how other associates interacted with the customers and then come up with some icebreakers to try and get the customers interacting with the jewelry (a customer is more likely to buy if they hold the jewelry or try it on).

One night two older ladies come up to the front counter…

Me: “Hi, how are you tonight?”

“We’re good, just looking.”

“Ok, let me know if there’s anything I can pull out for you to fondle.”


#17 The School of Awkward Silence

I was at the movies years ago with my then boyfriend, now husband. When we were buying the tickets, she asked if I was a student (students get discounts).

In my head, “I go to the School of Hard Knocks” sounded terrific. It sounded like a rebellious guitar riff. It sounded like unicorns. It sounded like eagles screaming. Like I would pull down my shades and saunter away.

OUT LOUD? Sounded tremendously lame. Groans. Facepalms. Deep burning shame.


#18 Hands-On Experience On Learning What Not to Say

I was in art class, and my teacher only had half a hand (till her elbow) on her right hand.

She was carrying some equipment, and without thinking, I said, “Do you need a hand?” The whole class gave me a horrible look, and I had just realized what I had just said. The funniest part was her response.

She looked at her hand and said, “Well, I need half.”


#19 They Will Start Calling it Leg Camp After This One

I was in boot camp (Navy) and we did these things called stealth jumping jacks. All eighty of us had to do them in two lines, only clapping on the fifth repetition. After two hours doing these things, starting all over with five more being added every time someone messed up, I got put in charge of getting our timing down. I had everyone freeze with their legs open and hands up, then went around behind one of the lines of recruits. I said in my loudest voice, “Everyone look between your legs. If you can see me there, you’re doing it right.” We laughed so hard that the chief came in and exercised us all night.


#20 How To Get Arrested At The Airport

I packed my carry on bag really full for a flight to California and when my bag was pulled for additional search I said to the TSA officer

“Careful when you open that, it might explode.”


#21 That Joke Isn’t Going to Slide

I am out at Dallas barbeque and my girlfriend and I noticed this African-American family arguing next to us. The kids (around 15 and 9) couldn’t do anything right by their mother who seemed to be mad at the world. The 15-year-old, pants sagging and all, gets up to go to the bathroom and as he slides through our table his butt passes over my coffee. The mom starts scolding him. Here’s my chance to make everyone feel better by making a joke. I say “don’t worry, I like a little chocolate in my coffee.” I was ultimately trying to make a poop joke.


#22 That’s Pretty Harsh

A girl that had an obvious crush on me in high school flipped me off for something sarcastic I said while we were hanging out in a big group and I responded, “Only if you were pretty and I was desperate.” I thought I was funny, but I found out she went home and cried. I still feel bad 15 years later.


#23 I Bet She Didn’t See That Coming

A blind lady who had lost her guide friend had gone up to a friend of mine to ask for help. My friend decided to call me over and asked me to help her find her friend.

I had no idea what to do, so I just asked what her friend’s name was, and after that… I don’t know why, but I asked: “what is she wearing?”

This blind woman looked so distraught after I asked that, and only said “…I don’t know.”

As soon as those words came out of my mouth, I was like “Oh no…” so I just walked away because I didn’t know what else to do. Which probably wasn’t the best thing to do either.


#24 She Couldn’t Handle the Naked Truth

“You look even better with your clothes on.”

Not at all what I meant. I meant that the girl I was talking to looked beautiful no matter her level of undress. Nerves and speaking before my brain worked out the words made for an awkward moment. As if being undressed in front of somebody for the first time isn’t nerve-wracking enough, I had to blurt that out.


#25 That was Literally the Worst

I worked at a Christmas Day soup kitchen several years ago. One of the guys I was serving asked if there were any whole wheat rolls instead of the plain white rolls. Without any hesitation, I said, “Sorry, beggars can’t be choosers.”


#26 You Should Have Thought That One Through First

My wife is pregnant and we were getting ready to go to a wedding. She put on her dress and said she felt fat because she was a few weeks pregnant. I told her, “you don’t look any different than you usually do,” which to her sounded like, “You always look this fat.” I know what I meant. After that, I said, “Your hair is pretty. I think I hear the phone ringing! I’d better go and answer it!”


#27 He Probably Had to Pay Extra for that

A very friendly ticket counter girl was being chastised to be faster and less chatty by her supervisor at the next counter. I smiled and said, “Wow, she’s really a slave driver…”

The ticket girl was black, and of course, the supervisor was white. Yeah, engage brain before opening mouth.


#28 Never Compare Anyone to Hitler

In a group therapy session, one of the other people was saying they felt like a horrible person for being under the influence and driving while their kids were in the car. I attempted to explain how in my opinion people are not inherently evil but we can do bad things, not making us bad people. Instead, I said I don’t think anyone is a bad person, we just make bad choices, even Hitler or Stalin. Instant silence followed by extreme facepalm by me.


#29 That Joke Will Make You Lose Your Appetite

My group and I had a party to celebrate our friend returning from rehab for anorexia. I took some bagel bites out after she arrived and said, “I hope everyone’s hungry!”


#30 I Hope you Had a Good Read

While I was cashiering, the old man I was checking out was basically telling me his life story. Before he left, he said “I hope you have a good life” and I responded, “I hope you had a good life.”


#31 Forgot How To English

I was on the phone with somebody that was struggling with depression and life problems. Before I said bye, I wanted to say,” I hope everything will fall in place for you,” but ended up saying, “I hope everything falls apart for you.”

Dearest friend, forgive me. I couldn’t English that day.


#32 Always Stay Hydrated

Sophomore year of high school. During sports seasons, I always made a conscious effort to stay hydrated. However, this led to me using the bathroom every other class.

One day, my History teacher noticed me walk out of the bathroom for the fourth time that morning… “Lumpaford, are you feeling well? You’re not sick or anything are you?”

“No, sir, I think I just drank too much.”

“……Well okay then.”


#33 Whatever It Takes To Get The Game

I was into a game buying mood one day and had enough money to make a purchase. I needed my Mom, however, to authorize the purchase since it was to be added as a charge to her card (I did not have one at the time). I was going to ask her and I meant to say, “I have a proposition for you” as the beginning comment.

Unfortunately, it came out as, “I would like to proposition you.” Cue awkwardness on my part when she explains to me exactly what I just said. I proceeded to back-pedal ask if I could buy the game. The answer, fortunately, was yes.


#34 They’re Just Being Honest

Server here. Woman asked me what I recommended. I said, “Middle aged women usually like the salads”.

I don’t even know what is wrong with me.


#35 Well, That Backfired

My girlfriend and I had a chance to move out of the country for my work and the company would pay extra if we were married. I suggested that we quick hit the courthouse and do a legal wedding. Followed it up with “It’s not like we would really be married.” Big mistake.


#36 Wrong Question

Ran into a friend at a bookstore once and chatted a little. Was trying to be nice so I asked about her family. What I said was “So how’s your mom doing these days?”

Then I suddenly remembered her mom passed away a couple years ago.


#37 Too Soon

My boss is pretty laid back. More than I am. He was making borderline disrespectful ‘too-soon’ comments about Paul Walker. This is the day after Mandela passed. So someone says “maybe it’s too soon for walker jokes” and without thinking I chime in, “Did you guys hear that Morgan Freeman died?”


#38 How To End A Friendship

Me and my best friend were at Outback eating some cheesecake for dessert. She eats hers really fast and proceeds to say, “Where’d my cheesecake go? I only meant to take a bite.” Then I being the genius I am said, “Your thighs.”

She wouldn’t talk to me for the longest time….


#39 An Accidental Psychic

Sister-in-law was getting married and I meant to say something about how I always knew she’d have a beautiful wedding, but it came out, “She’ll have a beautiful wedding no matter who she marries.”

My mother-in-law clearly thought I meant I didn’t think this wedding would work out. Interestingly enough, it didn’t. Also now I think I’m psychic.


#40 Creepy Pick Up Line

I met a woman who had the most beautiful eyes I’d ever seen, like swirling green galaxies of a million shining stars.

In my head: “Wow. Those are gorgeous. Like works of art. They’re so beautiful they should keep them on display for all mankind to see forever.”

Out of my mouth: You have pretty eyes. I bet they’d look good on a pedestal.

Happy ending: We’ve been married for six years now.


#41 Her Husband Was Amused

I do martial arts, and I was out at the pub with some non-sporty friends, I bumped into one of the guys from the gym and it took me a few seconds to recognize him. I tend to recognize people by the gis they wear. Of course, stupid me comments on this “Oh, hi Jim, I almost didn’t recognize you with clothes on!”

My husband thought it was hilarious.


#42 The Reason We Watch Sports

I was at a baseball game with a few friends and one of the guy’s girlfriend.

Being a girl, she was talking about how she liked the players tight pants and that it made their butts look good. She didn’t care about the game, she was just happy looking at the players. I immediately thought about how way back in high school I would stay after just to watch the girls volleyball games. I didn’t care about the game, just checking out the girls.

Well, she says, “I don’t really care for baseball but damn! That player right there has a really nice butt”

What came out of my mouth was a simple, “I know what you mean!”

Everyone for a few rows in front and behind us heard it and started chuckling after I said it, and I was too frozen with embarrassment to explain what I really meant.

I just left it at that. My friends didn’t, they still bring it up


#43 It’s The Thought That Counts

A co worker of mine lost a ton of weight and was looking really good. Well, when we got bought out by another company, we had a party and I put together a slideshow.

She was standing next to me and an old picture of her came up and I said, “Woah! Look! It’s fat Heidi! That’s so weird. You look so good now.”

I thought I was complimenting her, but later that night I realized how mean it really sounded.


#44 Bad Memory

My friend had the worst week of his life recently. He lost his job, his dog died, and his house was foreclosed so he had to move out.

At the job he worked at he had to wake up really early so when we hung out I accidentally asked him if he had to go to sleep to wake up for work on time.

I immediately apologize for bringing it up and we started laughing. in the midst of our laughter I say forgetting the rest of his circumstances, “If something terrible happens to me like my dog dies, you can make fun of me.” Then I remembered again.


#45 Unintentional Double Entendre

I delivered a large pizza to an extra large fella. It took me awhile to find the place. Well I finally got to his door and handed this robust man his pizza– I looked him square in the eye and said, “I’m sorry about your wait.”


Sources: 1,2