People Share Their Worst “Why Did I Say That?” Moment

You know, we’re not always in control of what we say. I mean, that’s a paper-thin argument, but sometimes we truly can’t help the foolish things that tumble from our mouths. There’s not really a good way to defend the poor things you say at a funeral or to your future in-laws.

#1 Webbed Feet

One time at the dinner table, my ex asked me about a slight webbing on my toe. She asked, “How do you get that?” In front of her entire family, I instinctively just replied with, “Inbreeding.” Forks dropped and they all just stared at me. I didn’t know what to do or where to look. I just wanted to disappear!


#2 Swallow Me, Earth

This happened when I was in fifth grade. There were about 300 kids in the auditorium for a D.A.R.E. presentation. A speaker started off by having all of us scream “Why?!” whenever he would say a statement. He’d then ask us “Do you know why?” Fast forward to the middle of the presentation and he asked “Do you know why?” again. I screamed “Why?!” so hard it could be heard in the cafeteria. Nobody else did. Swallow me, earth.


#3 Visiting Friends

I went to visit a friend with my sister, who was working on a college campus. She took us around and I don’t know what led to it, but she told us how she got attacked by a kid in middle school. She told us about the aftermath and how she was totally fine now. Eventually, it came time for my sister and I to leave. As we were saying our goodbyes and walking away, I said, “Don’t get attacked!” To this day, I want to punch myself in the face repeatedly and I have no clue why I said that.


#4 Into the Wall

I work in a hospital and I was taking a patient in for an X-ray. The patient was in a wheelchair. Trying to make small talk and keep things light, I said, “I suck at steering these things. I’ll try not to drive you into a wall.” The patient had just spent six weeks in bed, seriously injured after driving into a wall.


#5 Are You Sure?

On the morning of my wedding, the third time I’d met my soon-to-be mother-in-law, I was understandably jittery about the day. Probably not at the top of my game. So, I warmly greeted her by saying “Hi Linda! It’s so good to see you!” She was quiet for a moment, and then said, “Actually, it’s Laura.” I knew it was Laura. I have no clue why I called her Linda. I was mortified and felt like I had only one way out of the situation. I replied after a pause, “No. I’m pretty sure it’s Linda.”


#6 Stress Relief

I was in an interview for an administrator in a doctor’s surgery. It seemed to be going well and I got through the majority of questions with no issues. There were no real concerns about my experience or work history and they seemed pleased with what I said. Just three or four more questions and the interview would be over.

The interviewer asked, “This job can be very stressful, what do you do to release stress?” I just replied with, “I’ve always felt less stressed after I’ve been in bed with someone.” The interviewer and his assistant completely lost it and burst into laughter. The interview effectively ended there and then, and no, I did not get the job.


#7 I Do Not

Back in the seventh grade, a teacher called on me to answer a question. I guess I was a little sick at the time because I needed to clear my throat, yet decided against it because people might think I was gross or something. As you can probably guess, that didn’t work out well and I sounded like a chronic smoker. Finally, after trying my hardest to nonchalantly clear my throat, I announced to the class, “Sorry, I have a speech defect.” I do not.


#8 Care to Dance?

Not me, but my husband. He was out with his friends and a girl came up to him asking if he wanted to dance. What he meant to say was, “I only dance when I’m out of it, and I’m still sober.” But what he actually said was, “I’m not out of it enough to dance with you.” I wasn’t even there and I can feel that poor girl’s self-esteem drop every time he tells the story.


#9 How You Doin’?

My boss, an elderly dude, asked me, “How are you doing?” and he amused himself by following up with, “That reminds me of Joey from Friends.” The question was still directed at me, though. I responded, “Are you hitting on me?” He turned red and flustered and stammered, “No… no, no my wife is next door…” (She was visiting the office). Then straightened up and said, “That was inappropriate” and left my office. Why? Why did I say that?


#10 Cute Outfit

I once complimented a girl I know on her cute outfit and asked where she got it. She named a plus-size store. For whatever stupid reason I replied, “Really? I need to gain a bunch of weight so I can shop there!” I immediately realized what I had said and we looked at each other for a moment, looked away, and sat in uncomfortable silence for the rest of class because I’m the worst.


#11 Shall We?

This was about 12 years ago. I was chatting with two female colleagues during lunch break. When the break was almost over, I wanted to ask, “Shall we go back to work?” Instead, for some reason, I asked, “Shall we go to bed?” My face instantly turned red. It was pretty awkward, but we all ended up laughing about it.


#12 Standing Out

Back in the fifth grade, all of the students were at an assembly where the presenter told a story and would hold up cards for the audience to yell. When they held up the card that said “GASP,” everyone gasped. Meanwhile, I legitimately screamed the word “gasp” as loud as I have ever screamed anything in my life.


#13 Normal Western

I worked at a movie theater and an old couple asked for their money back after the half-hour grace period had passed on Brokeback Mountain because they thought it was going to be a “normal” Western. I said, “Well, it was set in the West. There were mountains and horses and herding. What exactly wasn’t ‘normal’ about it?”

They said it was the tent. I replied that it was a pup tent and they were pretty normal back in the ’60s. They said, “You know what we mean.” I said, “So what do you want me to write down? The manager just doesn’t let me pass out refunds willy-nilly. The gay stuff? Is that it?” When they complained to the manager, I was demoted to mopping the restrooms for the next month.


#14 Look How Big You Are

My co-worker’s pregnant wife was strolling into the office. At the time, she was about eight and a half months pregnant. I saw her and my 19-year-old mouth said, “You’re almost as big as your husband.” I didn’t think anything of it until an hour later when my co-worker and I had a chat about something called hormones.


#15 Baby Names

I remember very vividly this one time I accidentally made a pregnant woman cry. So, I happened to ask her what names she was considering for her baby. Somehow, this led to a conversation about our mothers (and the names they chose for us), which caused the pregnant woman to cry. I was mortified by what happened.


#16 Call of the Pickle

I worked at a restaurant that served fried pickles and it was one of our biggest sellers. I had two ladies come in and one said, “Oh my God, let’s get fried pickles.” The other lady said, “You go ahead, I’ll pass.” No biggie, but I ordered them and brought them out with two plates anyway. Now, what I meant to say was, “I brought two plates in case you change your mind. I know how delicious they are and they might call your name.” What I actually said was, “I brought two plates because I understand the call of the pickle.” Cue the awkward smile and walk off.


#17 Second Shot

I had a job interview that was “good cop/bad cop” I guess you could say. The first interviewer came out with some pretty tough questions and I was already a nervous wreck for the interview. I bombed. I felt like a total idiot for even thinking I had a shot. Then the second interviewer came out. I just blurted out, “Boy, did I mess that up!” He had a good laugh about it with me, we talked for 20 or 30 minutes and I started the next week. Still not sure how or why.


#18 Making Soup

I was at a group fitness class and the instructor was known for having weird exercises like bending and swinging one of your arms in a circle and calling it “making soup.” He got really into it and asked the class what soup they were making. Answers ranged from chicken and tomato soup. But when he asked me, I panicked and said water.


#19 Lock Those Doors

I got let go from my job by the boss. The firing was amicable and I understood why, but knew it sucked for both of us. Earlier that morning, though, my boss had chased a robber from his house. After the firing, I tried to lighten the mood when I walked out and said, “Keep your doors locked!” He did not think it was a reference to his earlier story…


#20 Try to Stall Him

At my friend’s wedding, which I was standing up in, I walked into the bathroom, which had one or two more men in it than there are stalls and urinals for. My friend said, “I guess I’ll use the handicap stall” since it was unoccupied. But, apparently he wasn’t sure that he should use it. Without missing a beat, I said, “That’s okay, it’ll work for you too.”

It was at that point that I realized that it wasn’t my friend who said it, just some guy I didn’t know who was in his 40s or 50s. Silence. I quickly went into the other stall, which someone had just exited, did my stuff as fast as possible, and left without washing my hands so I would get out of there before the other guy left the stall.


#21 Say Hello

At one point, I was out having some lunch with my girlfriend at the time. I remember asking her if she wanted to say hello to her friend, who I spotted. She told me that she didn’t see her. I pointed to her and asked, “Do you not recognize her bent over?” After I said that, all she could respond with was, “Do you?”


#22 Think of the Money

I have never responded well to random uncomfortable news. Once when I was in college, I was getting a haircut and asked how the stylist’s day was going. She said her day was going well but her dog passed away the night before. Without thinking I said, “Think of all the money you’ll save on dog food.” Instant regret. It’s one of those things that pops into my head randomly as I try to sleep at night.


#23 Is This a Joke?

When my husband proposed, he completely caught me off guard (we had talked about it, so I knew it was going to come, it just came when I was completely unsuspecting of it). He was on his knee, holding a ring with tears in his eyes and telling me how much I meant to him. I responded with, “Are you kidding me? This better not be a joke. If this is a joke, you’re the biggest idiot on this planet.”


#24 Belief in the Pope

I had a girlfriend in high school who had a super Catholic family. I met her dad and he asked, “Do you believe in the Pope?” I had literally seen a comedy special a week before where the comedian made a joke about that and used that exact question. So, I tried to lighten the mood and I used the comedian’s response, “Don’t you kind of have to? He’s a real guy.” Her dad didn’t like that.


#25 The Bus Stop

Seven years ago, I was working with event staff security. It was my responsibility to make sure the partied out people were standing by, in position for their shuttle buses after a baseball game. I saw these two friends, one was holding up the other. As I walked by, I heard the one say, “Shhh, c’mon! The bus is almost here.”

To which the other responded, in what I thought was a sarcastic tone, “Ooh, the bus.” I chuckled and commented, “I remembered my first drink.” Turns out, the guy helping the other was the father, taking care of his son that had had a traumatic brain injury two years earlier. I apologized profusely, but still feel like garbage.


#26 Mexican Wedding

My seventh-grade teacher was telling us about her sister’s wedding in Mexico. It was the first day back from summer vacation. I raised my hand and waited for her to call on me. I then asked if they had “mucho sexo” and immediately got kicked out of class. Now here’s the thing. On Letterman the night before, a guest was telling him about his Mexican wedding and Letterman asked if they had “mucho sexo,” which got huge laughs. Not everyone watches Letterman, especially not my teacher.


#27 Wow, That’s Strange

An ex was explaining she was self-conscious about something, and it was slightly odd. So, I intended to say something reassuring and comforting. What I actually said was, “That’s strange, of all the things you could be self-conscious about.” Her face dropped and I realized immediately what I said and unsuccessfully tried to backtrack.


#28 No, You Idiot

I took my girlfriend to a very beautiful park and served a gourmet picnic. After we were finished, I nervously took her hand in mine and asked her to marry me. I mumbled, or her ears failed, or I don’t know what but she replied with, “Sure, whatever,” obviously missing what I had said. In my mind, I thought, “You idiot. You messed this up.” But out of my mouth came the words, “No, you idiot. I’m proposing.” Yes. I called my wife an idiot as part of my marriage proposal. After that, I kind of blanked out until I saw her crying and saying yes over and over. Our 18th anniversary is coming up in the spring.


#29 Something in Common

I was 15 and in the early stages of my emo phase, so I wore skinny jeans. Except they didn’t make skinny jeans for men at the time, so I wore girl jeans, just as many of my male, skinny-jean-bearing friends did. I went to a birthday party at a local restaurant, but I didn’t normally speak to anyone there except the birthday girl and another one of my buddies.

This, alongside my social awkwardness, made it difficult to think of a conversation topic. The girl across from me got up to go to the bathroom and I noticed that she had a familiar pattern on her jeans. As she came back and sat down, I immediately said, “So, I noticed we’re wearing the same jeans.” I still think about it eight years later.


#30 Sort of Punk-tual

I was interviewing for my first job and was probably 15-16. It was a job bussing tables and washing dishes at the golf club. During the interview, the interviewer asked, “Are you punctual?” I replied with, “I think you can tell from my appearance that I’m not punk at all and I don’t really like that kind of music.” Next question, “Are you frequently on time to appointments?” I answered normally, thinking it was just the next question.


#31 I Don’t Know You

I was at a water park with some friends and I ran into an old work buddy who was there with her friends, one of which I also worked with. She was really cute and wanted to give me a hug. The problem was I didn’t recognize her at first because she was in a bikini and we didn’t really talk outside of work. I was really nervous, so I backed off and said, “Well, I don’t really know you that well.”


#32 Bowl of Punch

My friend and I were at our mutual friend’s birthday party when we were about six or seven. The mother brought out a bowl of strawberry punch. To be fair, it really didn’t look super appealing but my friend couldn’t keep her mouth shut and said something along the lines of, “Wow, that looks like a bowl of poop.” The mother got super upset and offended and I could see immediately the look on my friend’s face that she knew she messed up.


#33 Yeah, Go Spongebob!

Do you remember that one episode of Spongebob where Squidward is in a talent show and no one will clap for him, but then when Spongebob comes out to mop the floor, everyone cheers? Well, one time in college, I was at this performance and after one of the acts, this tiny nerdy guy came out to mop the stage because there was spilled water or something. I screamed, “Yeah! Go Spongebob!” The auditorium went silent and everyone around me turned and stared. I left shortly after.


#34 What to Say

I went to a funeral for a friend’s dad, who I had never met. My friend wasn’t crying so I asked him, “Why aren’t you crying? Did you not love your dad?” I suddenly realized that my brain filter had grossly failed me. He replied that he was all out of tears as three days had passed since his passing. I felt like an idiot and left within just a few minutes. Ever since that, I worry about what to say at funerals.


#35 Taking Everything

One time, I was talking to my mom, who was recently divorced from my dad. I asked about an old door that used to be in the garage rafters at their house, asking if she had that or not, which she said she didn’t. I then stupidly said, “I’m surprised you didn’t take that since you took everything else from him.”


#36 Math on a Saturday

I was a math tutor for grade school kids at a franchise place. One day, a middle-school-aged girl came in several hours after the time she usually does (we didn’t do appointments, the kids usually followed routines). I asked why she was coming in later than usual, just making small talk. She said she went to her grandmother’s funeral that morning.

So I said, “Well, at least that’s better than doing math on a Saturday!”, trying to joke around. She kind of sheepishly faked a smile and I immediately realized I’m an idiot and walked away. Yup, I walked away from her instead of apologizing. I didn’t speak to that kid again for a while. Because I’m an idiot.


#37 Look in Your Pocket

Before I was proposed to my girlfriend, I had everything all planned out. I casually handed my now-wife the ring box and said, “Hold this for a second” from behind. I then got down on one knee. She just pocketed it and turned around, wondering why I was on one knee. I then said, “Look in your pocket, you idiot.”


#38 Um, Excuse Me

A few years ago, my wife actually walked in on a burglar in our living room. Thankfully, she was totally fine, the guy ran away and didn’t take anything or hurt anyone. However, when my dear wife saw him there, she just screamed, ” Um, excuse me!” For days after the event, she kept asking me, “Why was I polite?”


#39 Haha, Dang

I was at the store a while back, making small talk with the cashier during checkout. The dude was telling me about how one of his friends got hit by a car down the street a few nights ago. The major injuries were sustained, but they still got hospitalized and freaked everyone out. My response? “Haha dang, well maybe you should have less friends!”

My ears started burning immediately and he kind of let his voice trail off while finishing up the transaction. I later called the place, asked to speak to him, and apologized profusely for saying such a stupid thing. He was laughing about it, thankfully, but agreed that it was out of left field and that he had no idea how to respond.


#40 Boss’s Baby

My wife and I were having dinner with her boss (B) and B’s husband and new baby. The baby had a loose pocket of skin on her head. My wife had mentioned it before, so I was aware but not really thinking about it. I couldn’t see it at the angle that the baby was being held at. B moved the baby to hold her with the other arm, and I saw it move. It was like a large, fleshy blister. I quietly exclaimed, “That baby needs a hat!” B shot daggers out of her eyes at me while her husband suppressed a laugh.


#41 What’re You Trying to Do?

I went to a funeral last year for my co-worker’s father who had just passed away. I was standing there with a couple of other people when someone accidentally bumped into me and quickly apologized. However, the first thing that came out of my mouth was, “What? Are you trying to kill me?” Cue the painfully awkward silence.


#42 Typical Teenager

My mom’s mom passed away when she was young (maybe seven or eight). We were at dinner when I was about 14 and typical teenager me was arguing with my mom about something and she said, “Well I’m the mom, that’s why.” I followed up with, “How do you know that you’re being a mom the right way? Yours is gone, so you don’t even know what a good mom is like.” My mom promptly started crying and walked out of the restaurant, leaving my dad glaring at me. I apologized profusely many times, but she never forgave me.


#43 Hoping for the Best

My friend was talking to me about some random stuff while she was getting changed, and I wasn’t really paying attention. My replies were mainly “yeah” or “no.” I heard her ask me something (but I had no idea what), so I just smiled at her and said “absolutely” and hoped for the best. Turned out, she asked me if she looked fat.


#44 Can You Stop Eating?

My husband proposed to me at a restaurant. We had just finished dessert, which was some sort of cake. He started to say something and I casually picked up my fork and used the back of it to smush the crumbs and eat them. Of course, he got all flustered and said, “Oh my God, can you stop eating for a second?!”


#45 Free Desk

In eighth grade, there was this pretty girl that I sat next to who had a reputation for being depressed and sleeping around. In retrospect, she probably had a lot of emotional issues from her upbringing. One day, she asked me, “What would you do if I passed away?” The first that came to mind was, “I’d probably use your desk to put my books on.”


#46 After School Plans

I was in Spanish class (I suck at Spanish) and we were going around the room, saying what we were going to do after school. After we answered, we’d then say who we wanted to speak next. I’m a dude and I was sitting next to my friend, who I’ll call Hannah. My plan was to say, “I was going to do homework” and then say Hannah so she’d go next. But I forgot the homework part and just said in Spanish, “After school, I’m going to do Hannah” The whole class started laughing (including the teacher).


#47 Like the Bathroom

Before my brother came home from university, we cleaned the house and everything smelled pristine. After he got back, he went into the bathroom and noticed how nice it smelled. Then he went into the kitchen, where my mother was cooking dinner. He proceeded to tell her that her food smelled like the bathroom.


#48 Fair Game

Luckily, nothing ever came of it, but one time in 11th grade, this girl in my algebra class fell asleep in the back of the room. My friend was recording her cause she was snoring, and on the recording you could hear me say, “If this was a party, she’d be fair game.” I meant drawing on her face, not anything else.


#49 Brightest Tool

This one time, I was having an argument with my partner. The main reason we were bickering was because she had a problem with me correcting her all the time. She said, “I know I’m not the brightest tool in the shed, but there’s no need to always correct me.” I couldn’t stop myself and all I said was, “Sharpest.”


#50 I Love You

Back in college, I was hanging out in my apartment with my roommate and a couple of girls came over, two sisters. We knew one of the sisters, but the other had been away doing a study abroad, so we were meeting her for the first time. My roommate introduced himself to this girl as “I love you.” I’ve never cringed so hard for someone else in my life.