Glimpse Into the Unexpected Questions People Confess They've Been Asked

We've all been in an awkward situation. Someone asks something you didn't see coming or makes a comment that leaves you blindsided. The following people share their stories of the innocent, but crushing questions they’ve been asked. They also explain how the experience affected them in heartbreaking, awkward, or enlightening ways. Read on to explore the stories of these Redditors!

IT'S NONE OF YOUR BEESWAX

Image Credit: Wikimedia Commons

Image Credit: Wikimedia Commons


My four-year-old cousin once looked up and down at my acne and then asked me, “Why do you have so many bee stings on your face?” I had been suffering from bad skin for a while and even though this question was harmless, it sure stung like a bee! I wanted to cry!

In my sadness and anger, I wanted to tell her that what was on my face was none of her beeswax but instead I just walked away. Afterall she was just a child and in a couple of years when she went through the same phases, she would know exactly why I had so many "bee stings" on my face. 

THE SYMPATHETIC HAIRDRESSER

Image Credit: Pixabay

Image Credit: Pixabay


I went to get a haircut for my fiancé’s funeral which was happening on the weekend. He passed away on Tuesday and my hairdresser didn't know. So she, all bubbly, said, “It’s been a while!! The last time I saw you, you were just about to move in with your boyfriend! How’s it going?” The words stuck and I kind of couldn't get out any words.

To be honest, though, her reaction was so wonderful and sympathetic. She was behind me, and just put her hands firmly on my shoulders and looked me in the eyes in the mirror. No shock, no stupid comments, just silent, genuine empathy. The rest of the haircut was pretty quiet, but she did her best to make me feel okay.

BABY TROUBLES 

Image Credit: Pxfuel

Image Credit: Pxfuel


I teach first grade and was talking about how I’ve been married to my husband for five years. One student asked, “How could you not have a baby by now?” Not wanting to explain all my issues with trying to get pregnant to a classroom of six-year-olds I said something more fitting for the occasion.

I said, “Being around all of you makes my heart so full that I don’t think I have room in my heart for a baby!!” They all smiled. I smiled too. I’ve learned from my experience to never ask couples when/if they want to have a family. May we all become more sensitive when we speak to people because we never know what they are going through.

THE NOSY FRIEND

Image Credit: Peakpx

Image Credit: Peakpx


What happened to me was downright sad and humiliating. A friend looked at me and said, “I know we’ve talked about it before, but how did you break your nose?” We had never before spoken about my nose and to make matters worse, I’ve never broken my nose. This is just how it looks. Ouch!

ADAPTED PLAYTIME 

I am disabled and though I have come to make peace with it, some questions still hurt and remind me that I will never be like other people. My niece asked me this seemingly innocent question, “When will you get better so you can play with us?” It hurt even though she didn't mean for it to hurt.

Image Credit: Needpix

Image Credit: Needpix


My niece who was too young to understand what disabled meant really meant her question back then. She’s older now and understands I will never get better. And we have adapted playtime to do things I can handle as well. But, the fact remains, her question broke my heart a little.

THE THREE SHIRT HURT

I grew up lower-middle class and my parents had been severely injured by a drunk driver at the end of my eighth-grade year. They were disabled and no longer able to work so our lifestyle was very limited. We basically had no money for school clothes, but my mother tried to get me a few cool shirts. I wasn’t a popular kid and most people didn’t really know me.

Image Credit: Peakpx

Image Credit: Peakpx


In my freshman year of high school, one of the popular girls in my class asked a question that I will never forget. She asked, “Don’t you have more than three shirts? I only ever see you wearing the same three shirts.” While I don't think she meant to insult me, the question crushed me because it reminded me of my situation. 

CASHIER'S HAVE A HARD TIME

One day I was working the tills and I had an awkward checkout, to say the least. “What’s on her face, mom?”—A little girl who had not yet gone through puberty. I used to be a cashier and had terrible acne at the time. She really had no idea what was waiting for her a few years down the line. Good luck to her!

Image Credit: Wikimedia Commons

Image Credit: Wikimedia Commons


A SHACKY QUESTION 

“Rough night last night?” is a question I am usually asked with a big smile. I was asked that all the time when I was younger because I had an obvious tremor and would shake all the time. The thing is, I did not drink or do drugs at all and I had no idea what was wrong with me. It was hell brushing off the questions which actually had nothing to do with the person asking it.

Later in my life, I was eventually diagnosed with Graves’ Disease and treated for it, but that doesn't take away the years of humiliation and crushing experiences. I still have a bit of a tremor in my body and people still ask me questions about it when in fact, they should rather just keep quiet if I'm being honest. 

THE AWKWARD NON-VERBAL QUESTION

Image Credit: Pixabay

Image Credit: Pixabay


The question was nonverbal, but it was a loud question none the less! The nurse at the flu shot station seemed unsure whether to give me the under-65 or over-65 consent form. I could see the confusion in her eyes and I didn't know if I should tell her my age or just let her guess.

I let her guess and soon realized how old I looked... If I’m going to be mistaken for being that much older than my actual age, at least it should be in the context of me getting a senior discount. Next time I'll be sure to use my mature looks to get some kind of discount benefit out of the deal! 

A GREY AREA

Image Credit: Pixabay

Image Credit: Pixabay


My grandma’s hair has been a pale white since she was 23, and she has been getting offered senior discounts since she was about 30. She used to get offended by it and their comments would hurt. To be fair her hair did make for a grey area. But now she sees it as a kind of life hack that gets her free stuff sometimes. She still isn't 65!

MISTER UNPOPULAR 

I've often been called a staying homebody. This is because I have never been popular and always sat b myself. Someone once asked me this stinging question, “Why don’t you ever go out?” Well, because I don’t have anyone to go out with. Dang…the truth hurts sometimes. I still don't have many friends but have made peace with it.

Image Credit: Wikimedia Commons

Image Credit: Wikimedia Commons


A PAINFUL DETAIL

I was at a specialist appointment and they did the normal thing of checking my contact details and address. Everything was going fine until they asked about my wife. They asked if the contact number and details for my wife were still correct, and I just started crying. I wasn't prepared for the question so soon after her passing.

My wife passed away this time 12 months ago. Although it's been a year, the reality of it still hasn't sunk in. Surprising how much one simple question asked in total innocence can bring you to your knees. I can't blame the specialist for just doing their job but the experience was rather crushing. 

AN UNFRIENDLY QUESTION

Image Credit: Wikipedia

Image Credit: Wikipedia


I once had a friend who gave me a rather tough friendship quiz. I had no friends in summer school and a girl asked me if I had any friends. Like straight up and to the point, “Do you have any friends?” She then became friends with me, but still, the question kind of burned as I realized how lonely I was. 

THE MASTER OF NONE

“So, when are you going back for your master’s degree?” Now, this was a question I didn't see coming. I was so proud of getting my bachelor’s and had no intention of going back because of how rough school was for me. I thought now that I had studied a bit more people would have respect for me.

Image Credit: Pixabay

Image Credit: Pixabay


I never knew how wrong I was in thinking that! I just began to see how much leaning there still was to do and how little a degree actually meant these days. After slaving away at school I still got no recognition. I may have an undergraduate degree but to many, I will simply just be the master of nothing. 

MOM DIDN'T GO FOR GOLD

When I was 13, my mom got a divorce from a man who I can only refer to as a “step monster.” I worked all summer to save up money since we didn’t have a lot and I was worried we wouldn’t have enough to pay the bills. I ended up having a few dollars leftover and wanted to buy my mom a gift to spoil her. 

Image Credit: Needpix

Image Credit: Needpix


She mentioned she needed a new watch, so for her birthday I went to the jeweler and got a $100 gold Citizen Evo Drive watch. It was functional and it looked really nice. When I gave it to her, her first response was, “Thanks honey, did it come in silver?” I was crushed. Insult to injury: she started dating a guy who e bought her a silver watch. 

DADDY'S GIRL

People thought my girlfriend at the time was my daughter. It was always very awkward because we could see people stare at us. We were only two years difference in age which made it even more insulting. People tell me I look super old but I was only 22 and now a very insecure 22-year-old... 

CARTOON DREAMS 

Image Credit: Pixabay

Image Credit: Pixabay


I work at a pretty boring convenience store and my neighbor down the street, a 12-year-old kid was there. The good kid usually hangs out there and talks to me. One day I was drawing cartoons for him by his request and he said, “Wow you’re really good at making cartoons, why don’t you just quit this job and make comic books?!”

It really bummed me out because when I was his age that’s all I wanted to do but was never financially given even the slightest opportunity to go to school for something like that and I’ll never have the motivation for stuff like that when I’m working 50+ hour weeks in retail just to barely make ends meet. 

CRYING EYES

Image Credit: Pixabay

Image Credit: Pixabay


Someone jokingly asked me if I was high because my eyes were red. I had just been diagnosed with an eye disease and told I would go blind before 50. My eyes were red from my medicated eye drops and partially from crying. I was only sixteen and having a hard time coming to terms with it so the question really stung.

THE WEIRD QUESTION

People can be very mean and insensitive sometimes. I learned this the hard way. Someone once straightforwardly asked me, “Why are you so weird?” I knew that I never really fit in, but I’m not sure why this question crushed me so much. It was like a confirmation of how different I was and it made me sad at the time.

WHERE'S GRANDPA

Image Credit: Pixabay

Image Credit: Pixabay


My five-year-old cousin asked me where Grandpa was when we were getting ready to head to his funeral. Everyone went silent and we just kind of stared at each other until my dad managed to distract her. It was brutal and made us all face the reality that our grandpa was in fact never coming back. 

THE ONE MEAL MAN

A co-worker innocently asked, “Who does the cooking at your house?” While the question would seem normal on any given day it really crushed me. I had very recently separated from my wife and was living alone. Her question just reminded me that I was alone and it brought back all the emotions. 

Image Credit: Flickr

Image Credit: Flickr


THE FOOD BABY

This question was harsh but it did give me a rude awakening to turn my situation around. Someone asked me a question no one should actually be allowed to ask until you tell them you're expecting. She asked, “When are you due?” I wasn’t pregnant and it was awkward. I have since lost over 60 pounds though.

GREEN WITH ENVY

I've never really been a jealous person but this question left me green with envy. I was a freshman in high school in 1992-93. My high school science teacher asked me if I was ever jealous of my older brother (he was a senior). I was kind of confused. The reason left me speechless and opened up huge insecurity in me. 

Image Credit: Piqsels

Image Credit: Piqsels


She said, “You know, since he is so smart, popular, and just has everything going for him…” It was the first time I had ever, in my entire life, considered that people viewed my brother as better than me. It has honestly kind of stuck with me to this very day. That was 26 or 27 years ago. I still remember it. 

MOM SAID NO TO PSYCHOLOGY

I always wanted to study psychology in college, but my overbearing mother wouldn’t have that, so I studied chemistry. In my last semester, I took an abnormal psychology class just for fun and I crushed it, ending with a 99% average. A mark I was proud of until I was asked the following question.

Image Credit: Needpix

Image Credit: Needpix


After the final, my professor took me outside the classroom and said, “Why didn’t you major in psychology? You would have made a great psychologist.”That really crushed my soul. I think about that day a lot. I can't help but wonder how different my life would've been if I followed my gut. 

CONSTRUCTIVE CRITICISM

Why are you so stuck up and never talk to anyone?” I was cripplingly shy all through school. This was asked by a girl I didn’t even recognize, at the end of summer school after my senior year. It was the last credit I needed to graduate. At the time it was shocking and crushing and left me feeling heartbroken.

Image Credit: Pixabay

Image Credit: Pixabay


But later it helped me reevaluate things I was doing, like body language, that I realized made people think I was antisocial. I’d always wondered why people reacted so badly to me when I really wanted to make friends. I managed to change a few small things that led to small positive interactions.

After which I was able to become more and more confident. I still feel really shy, but I’ve learned how to fake it until I actually get comfortable with people, and now nobody even believes me when I say I’m shy. So in a way, that once crushing question really helped make me who I am today.

SAW RIGHT THROUGH MY BRACES

Image Credit: Flickr

Image Credit: Flickr

Someone once asked me a question that left me both embarrassed and ashamed of myself. On my see-through braces: “Why didn’t you just get yellow ones?” Suffice to say I soon went to the dentist to get them cleaned. I also never ever spoke to that person again. I'd been embarrassed enough. 

LONGHAIRED LADIES

I was rudely made aware of how I looked one date night. At a restaurant with my wife. The server walks up from behind and says, “Ladies, how are we this evening?” I’m a guy. It must've been my long hair that confused him but it still got to me. The server also felt really bad afterward so that was at least a consolation. 

Image Credit: Piqsels

Image Credit: Piqsels

MUSICALLY CRUSHED 

I worked for years as a professional musician, mostly doing cruise ship gigs, but also live shows and a bit of studio work. I really enjoyed my job with music but I was never able to fully commit to it. This question hit me hard. “Why aren’t you doing music anymore?” Cause my passion got crushed by the industry, that’s why.

DIRECT-OR ATTACK 

A veteran actor on set two days into production asked me who the heck the director was. It was me. I never got over the look on his face when I told him I was the director. His question really crushed me and stuck with me for many years. I still doubt my directing abilities and to be honest, I think I always will. 

Image Credit: Wikimedia Commons

Image Credit: Wikimedia Commons


SINGLE BUT NOT READY TO MINGLE

I get this question a lot and it hurts every time. “Do you have a boyfriend?” “No.” “Oh. Why not?” Because I’m a loser, lady, and nobody wants me. It's not that I don't want a relationship it's that I don't really know how the whole dating thing works. I've been single so long I wonder if I'll ever find a boyfriend.

A LIPPY BEAUTY THERAPIST

I changed beauty therapists after the subtle rude comment at my last appointment. I may have been too sensitive but she shouldn't have asked me the question. I went to get my eyebrows waxed and the lady said, “Lip too?” No, I never asked for my lip. If I wanted it waxed I would've said so. She did my lip anyway.

Image Credit: Flickr

Image Credit: Flickr


OFF TUNE 

Me: “Babe, do I have a good singing voice?” Babe: “I don’t know, have you ever sang around me?”……I sing almost every day. After the question, I realized that he was either being nice y avoiding the question or he really never paid attention to me. Either way, I knew my voice and our relationship was off tune. 

HAPPILY NEVER AFTER 

“How’s married life going?” It was a good six months that acquaintances kept asking me the question after my fiancé broke up with me days before the wedding after a two-year engagement. It made it so much harder to get over it. What made it worse was the reason for our breakup. It haunts me more than the question does.

Image Credit: Flickr

Image Credit: Flickr


He was cheating on me, and on the same weekend as our wedding. The story gets even worse because he went and married the other chick in Vegas. So, he didn’t have to deal with the same awkward questions I did. I'll never forgive him for the shame and embarrassment he put me through. At least I got away from the cheater.

THE UGLY DUCKLING

The following question has always stuck with me. It changed the way I view myself and my relationship with my sister and of course my friend, Danielle. "Does it bother you that your sister is so much prettier than you?” Yes, yes it does. Also, if you don't have anything nice to say, keep quiet Danielle!

EXPIRATION DATE UNKNOWN

Image Credit: Flickr

Image Credit: Flickr


The following question was equally as cute as it was saddening. My five-year-old daughter asked me the other day, “When do humans expire?” Followed by, “We’re gonna be together forever right? Until you’re 100?” Little does she know that our time together is always limited and we should make the most of it.  

IRISH OR ALBINO?

I was living in Las Vegas for a while and I was asked by my local liquor store clerk if I was albino. I’m just Irish. The comment was insensitive and took a knock at my self-image. I don't know if he was serious or not. But what I do know is that I certainly won't be buying liquor from his store in the future!

A BAD JOKE 

Image Credit: Needpix

Image Credit: Needpix


Sometimes jokes are funny and sometimes they are not. I’m an actor and I work in a restaurant. One of the girls got an acting job, and my manager turned to me and half-joking said, “Why can’t you do that?!” I brushed it off, but later that night I cried my eyes out and I never gained my confidence back completely. 

THE NOSY KID

In seventh grade, a girl I became friends with asked me: “Did you get made fun of because of your nose?” I had never seen a problem with my nose until this moment. 11 years later and I still haven’t forgotten and am incredibly self-conscious about my nose. People should think before they speak because words have power.

Image Credit: PxHere

Image Credit: PxHere


ACNE ADVISE 

“Have you tried this medicine?” I have adult acne and have had acne since puberty. I HAVE LITERALLY TRIED EVERY MEDICINE AND NATURAL THING IN THE UNIVERSE, please stop reminding me that my face is horrifying to you. I never understood why people felt the need to give advice that I didn't ask for. 

A REAL-LIFE FAT SUIT

Audience member after a performance: “Were you wearing a fat suit under your costume?” I was not. But thank you for reminding me about my weight problem. I never got over that comment and instead of losing weight, the question actually made me put on more weight. So thanks, rude audience member!

IS DAD PREGNANT?

Image Credit: Flickr

Image Credit: Flickr


My daughter who is seven years old asked me the following question while my wife was pregnant: “You have a big tummy like mommy. *suspiciously* Do you have a baby in there too?” And that’s the origin story of my 50 lb. weight loss. I guess her question spurred me to lose weight and was a good wake up call. 

A DUSTY SITUATION 

We keep our home clean and neat and we especially look after it when we have gues over. But a dinner guest once said: “You have such a nice home. How often do you dust it?” (as she looked with disdain at the furniture). Her question annoyed me and suffice to say, we never invited her over again. 

THE GOOD TEACHER

Image Credit: Flickr

Image Credit: Flickr


My third-grade teacher asked me why I don’t sit with my friends at lunch. I told her it was because I didn’t have any. From then on out, she became very adamant about me never changing for anyone and encouraged me to pursue the things I was interested in, like music. I really wish she knew the kind of lifelong impact she’s had on me.

THE NO MAKE UP TRICK

I wore no makeup the day before I planned to call in sick. It was all part of my plan to look a little bit more down and ill. Somehow it still hurt a little when my boss said, “Yeah you looked awful, don’t blame you.” I guess I brought the comment on myself. At least I got a day off as a reward for his mean comment. 

Image Credit: PxFuel

Image Credit: PxFuel


NO LONGER A WITCH

I used to work at a tutoring place and at the time my skin was filled with acne and I had a very pointy nose. A little girl I was helping with homework asked me if I was a witch because of all my pimples and big nose. It broke my heart but fortunately, one nose job and many acne treatments later, I’m no longer insecure.

A WEIGHTY QUESTION 

I was running a tray of food to a seat at a dine-in movie theatre. There was A LOT of food on the tray and when I brought it to the single person, I asked, “Is this all for you?” I didn't realize how weighty the question was until I saw her, She responded “Yeah” in a depressing tone. She was overweight. I still feel bad. 

UNFRIENDED

Image Credit: Needpix

Image Credit: Needpix


“So, this thing happened at [insert Friend’s name here]’s party/bonfire last week.” My friend had a party/bonfire last week? Nobody told me…And just like that, I realized who my true friends were. In a way, I was glad about it because I was able to make new and true friends in the future. Good riddance to them!

DREAMS ARE BETTER THAN REALITY 

“I had a dream that you had lost a lot of weight and we were getting married!” Those were words said by my best friend who I had a crush on. He was dating someone else and I was shattered by the comment. Why did he even say anything? His words were both crushing and rude. I'm still not over it and we're still not married. 

Image Credit: Public Domain Pictures

Image Credit: Public Domain Pictures


We feel so sorry for these people who were tormented and forever impacted by seemingly innocent questions. Have you ever been asked questions that left you feeling awkward or crushed? Leave your comment in the comment section!

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