September 26, 2018 | Carl Wyndham

People Share The Most Soul Crushing Questions They've Ever Been Asked

“Culture makes people understand each other better. And if they understand each other better in their soul, it is easier to overcome the economic and political barriers. But first, they have to understand that their neighbor is, in the end, just like them, with the same problems, the same questions.”—Paulo Coelho.

“Adult life is dealing with an enormous amount of questions that don't have answers. So I let the mystery settle into my music. I don't deny anything, I don't advocate anything, I just live with it.”—Bruce Springsteen.

Life is hard. There is no denying that. One way to get through it is by being there for each other. Yet, some people don’t get this and have a hard time being sensitive about the things that can be difficult for others. This can often lead to some soul-crushing moments when people ask us questions that we simply cannot answer or do not want to think about. Here are some of those question that crushed the souls of people, as told by Reddit.

Soul Crushing Questions FactsWould You Rather Questions

45. Nope, Just Bad At My Job

"First day on the job?"

Nope, I have been at it a decade and still suck. I am just too stubborn to give up.

Soul Crushing Questions FactsAdventure Time Wiki - Fandom

44. No Hobbies

“What are some of your hobbies/interests?”

I’ve never realized I don’t do anything faster than this question, every time.

Soul Crushing Questions FactsYouTube

43. That’s Not A Friendly Question

“Do you have any friends besides us?”

Soul Crushing Questions FactsGiphy

42. Asking the Wrong Question Yourself

So this is actually something I asked, but the response really sucked. I was in my freshman year of high school and was in the Air Force Junior Reserve Training Corps (AFJROTC). There was a leadership camp for students who excelled and wanted to become officers and I was selected to go. I was super shy and serious, so I didn't talk to a lot of people. The first time my parents came to visit was what some kids and teachers would say was the first time they'd seen me smile or laugh.

Anyway, I was a really good student and my teachers loved me, so I assumed that would translate to "boot camp." I did well in the camp and at one point asked my two sophomore training instructors what I could do to become a good officer and a training instructor and to give me advice.

They go on to tell me that I probably won't be a great leader because I'm too quiet and forgettable. I know I can be really quiet, but being told you're forgettable really hurts, even if it's true. It still sucks, great advice guys. High school was rough, and my 10-year reunion is next month... I know where I won't be.

Soul Crushing Questions FactsWikimedia Commons

41. Compared To The Sister

My older sister was one of the cool kids at school, I didn't talk much. One of her friends was talking to me during class.

She asked, "How come (sister) is so amazing, but you're just..." she didn't finish because I guess she realized she worded it badly. The friend is a nice person and I know she didn't say it to be malicious, but still...

Soul Crushing Questions FactsOpen Society Foundations

40. It Ain’t Easy Working at the Library

Currently, it's "Oh, you work in a library? That must be nice and quiet, right?"

In actuality, I'm considering leaving my well-paying union job that has excellent benefits because I can't take the stress of it anymore. A good day is just being surrounded by poverty and drug abuse without any incident, an average day is being called a witch by someone I had politely asked to stop using FaceTime or whatever in the library, and a bad—but not uncommon—day is having my physical safety threatened and hoping the police get there before the person decides to act on it.

It's really draining me, and the only reason I haven't left yet is that I lucked into this job despite having no college degree.

Soul Crushing Questions FactsSouth Wales Argus

39. Pies In The Tummy

"Is it a boy or a girl?"

It was pies.

The worst thing is that this was at a festival in Spain and my fiancé and I were chatting with two nice locals in the crowd who spoke no English. My Spanish wasn't good enough for "Oh, this is awkward, I'm not pregnant, I'm just a bit fat at the moment and this is apparently an unflattering dress, message received" so I put my hand on my tummy and tried to look proud while saying "no sé" just to finish the conversation.

I proceeded to get extraordinarily drunk in front of them so I like to think they went home properly horrified.

Soul Crushing Questions FactsYouTube

38. Pointing Out the Stutter

“You stutter a lot, huh?” Asked in many variations by several people I’ve met.

I’m a shy and nervous bean sprout of a human being and I stumble over my words a lot. I feel bad whenever someone points out or brings up my jittery speech patterns, ‘cause I’m trying my best.

Soul Crushing Questions FactsGenetic Literacy Project

37. Not A Funny Memory

My best friend's grandmother had Alzheimer's and was 90+. She looked at my best friend and told her she was absolutely beautiful, then looked across the room at me and was like "Who's that man sitting over there?" I'm a girl.

My best friend made a joke out of it and I laughed but it secretly crushed me inside because I've always been the less attractive between me and my friend, and as much as I know comparing myself to her is no good, I still do sometimes.

My best friend doesn't know how much that sucked for me. She just thinks it's a funny memory of her grandmother and I don't want to ruin that for her.

Die Welt

36. Disappearing in High School

"What high school do you go to?" A few people from my high school asked me this at a party once. Kinda crushed me because it reminded me how insignificant I was.


35. First Time in Nigeria

In Nigeria for the first time... a native asked: "Why are you so fat?" I died completely.

I used to get this all the time when I worked in Honduras! I wasn't even huge by any means, they're just so blunt. One time the little grandma across the street asked me and I just said, "I don't know!" And she said, "It must be all those beers you drink!" And I'm like, "...right." So now she's calling me fat and trying to call out excessive drinking?!


Just kidding. I said, "Haha, yeah, anyway, do you have any more baleadas?" because she was well-meaning and loved feeding us teachers.

Plus Mommy

34. Questions for the Teacher

I used to tutor math for grade-school kids. There were a lot of questions like these. My favorites:

"Mister, did those shoes used to be cool?"—a first grader.

"Hey, do you think we have the same handwriting?"—a kindergartner.

"What's your real job?"—a fourth grader.

Soul Crushing Questions FactsDaily Express

33. How Much Do YOU Make?

When I taught inner-city high school students, one of the assignments I had them complete was career research. It was an informative assignment for many as some still had unrealistic expectations about what it takes to enter certain fields, pay, and the day-to-day nature of the work.

One student was researching web development and said to me, “The Bureau of Labor Statistics says web developers only earn 67K a year; that doesn’t seem like a lot of money. What do you earn, Miss?”

Soul Crushing Questions - dailygreatest

32. Settling Without the Six Pack

A while back I had a huge crush on this girl, we were best friends and were spending a lot of time together. One night when I was particularly drunk I told her I hope she finds a great guy who makes her as happy as she makes me.

So she proceeded to show me pictures of this guy she had reconnected with from high school that she was infatuated with. She made sure to point out his six-pack abs in one of his shirtless pictures and told me about the wild sexcapades she was planning on having with him. I told her how excited I was for her but I think part of me died that night.

Plot twist: the other guy didn't work out, and we've been dating for a little over 3 years. We are planning on getting married next year.

Soul Crushing Questions FactsWeNeedFun

31. Heartbreaking Question From a Daughter

When my three-year-old daughter asked me if I liked spending time at work more than spending time with her... I tried to explain it to her that I have to go to work, and about money, etc. I don’t know if she understands fully but I cried inside little. To think my daughter thinks I don’t want to spend time with her and that’s why I leave for work every day... It’s heartbreaking.


30. How Did You Picture Me?

Not a question, but a family member at a gathering wouldn't stop talking about how good I looked and how much weight I'd lost.

I definitely had not lost any weight since I last saw them.

It made me wonder what their mental image of me they remembered was.

Soul Crushing Questions Facts4plebs

29. Red Headed Difficulties

My sister and her boyfriend of seven years get asked nearly every day if they are siblings because they are both gingers. It's a sore spot for them because some people imply incest.

Soul Crushing Questions Factselysejankowski

28. Looking Older

"Are you in your 40s?" I'm 30.

Soul Crushing Questions FactsShort Jewish Gal

27. The Power of Suggestion

"Are you still sick? You look sick."

After feigning illness for a few extra days off work.

Soul Crushing Questions Factsfunny memes

26. Learning About Your Bald Spot

Hairdresser asked, "What do you want to do about your bald spot?"

Didn't know I had one… thanks.

Soul Crushing Questions FactsMic

25. Weird High School Years

When I was in high school I was quite weird. My personality was weird and I had a tall gangly body that I had a poor sense of, making me awkward and bad at sports. I was a 6’0” tall blonde girl without any of the perks. There was a girl on my volleyball team, Jen, who was also my height and had the same length and color hair; we looked very similar. But Jen was... adorable. She was cute and quirky and popular and boys found her sexy.

A girl on my team one day asked me why Jen and I looked the same but the whole tall awkward Taylor Swift thing worked for her but for me it was just... weird. She wanted to know WHY it was weird for me. Like I don’t know, Gina, why are you a jerk? We all have questions we don’t have answers to.

Soul Crushing Questions FactsKancolle Wiki - Fandom

24. Wanting to See Daddy

"When can I go see my dad?" Asked by my five-year-old, whose dad chooses to not see her because he's too busy with his new wife and her five children. I have begged him to stay in her life, and he refuses. I just tell her he lives so far that it's hard to come visit... He lives thirty minutes away. It breaks my heart for her.

Soul Crushing Questions FactsADDitude

23. The Mustache Upsell

Getting my eyebrows waxed at the salon, the lady working on me asks, "Do you want your mustache done, too?" My mustache? I wasn't aware I had a mustache.

Soul Crushing Questions FactsScrewAttack - Rooster Teeth

22. Nothing Wrong With Adoption

"But why would you want to adopt? It's not the same if they aren't yours."

Because I'm infertile and riddled with a disease I would never wish upon my worst enemy let alone my own child. Also what the hell is wrong with adopting? People act like adoption is some horrible last resort thing if they can't have kids “the normal way” instead of the opportunity to be a parent to a child who just wants a home and a family that loves them. But no no, apparently I should be pitied because I'm happy with the idea of raising a kid that looks nothing like me.

Soul Crushing Questions FactsRomper

21. Acne Problems

I have severe acne scarring. I usually don’t think about it. One day I was walking home from the school bus in my JROTC uniform—it’s like an Army class for high school students here in the US.

The neighbor’s kid and his friend were playing outside and they said hi to me, then I heard them say as I walked away:

“What happened to his face?”

“He’s in the Army and a grenade exploded in his face.”

“Oh... makes sense.”

I find it hilarious ‘cause I never said that and he legit believed that. But also it made me so much more self-conscious.

Soul Crushing Questions FactsRefinery29

20. Rehearsing Answers

  • Yes, I am still single since the last time I saw you.
  • No, I'm not trying to remain single, it's just difficult.
  • No, I don't know when will I stop being single.
  • I don't know what to tell you, I must be ugly/toxic/cursed.
  • Yes, I will probably die alone, thank you!

Soul Crushing Questions FactsYourDOST

19. The One I Love

Didn’t happen to me but:

I worked in the back room of a small town food bank with an 89-year-old guy named Andy. He brought his wife Ruth in with him one day, and she sat in a chair for a couple of hours while he worked filling boxes. She had fairly severe Alzheimer's disease, and stared vacantly and muttered to herself.

When he finished, he walked over to her and offered his hand to her and said: "It's time to get going, Ruth."

She took his hand and looked up at his face and said in a weak voice, "Are you the one that I love?"

Soul Crushing Questions Factslanguageties

18. Dealing With Tragedy

My father was murdered less than six months ago by my younger sister and her boyfriend. Because my father was so influential in my life practically any question about how my life has been or what's new rips me up inside.

One night my father got jumped by her boyfriend because of something incredibly petty, money—which he never really had much because he was ALWAYS so generous with it. My father even took him out that night to go grocery shopping and cooked them dinner. My younger sister and her boyfriend stabbed and beat him. I got the call about it a couple hours later by my older sister. I will never forget her tone and the shaking in her voice. She picked me up from my girlfriend's house to tell me what happened in person.

It felt like my entire being was torn out of my body. He is my best friend and always motivated me to be the best that I could. He was so giving and had this aura of positivity and happiness. We never had the best of things and we moved a LOT. But he always made me and my sister's feel loved and incredibly special. I miss him every day. His name is Thomas Heath and you can look up the article if you'd like to read more about it.

My older sister and I talk about him and all of the incredible things he has done for not only his children but even strangers. I mean, he once picked up an absolute stranger caught in the rain just because he felt empathy.

It's tough but without the lessons he taught me I would be in a much worse position than I am.

Soul Crushing Questions FactsTakanta

17. Stop Shaking My Hand

"Oh, did you just wash your hands?!"

Nope, just really sweaty palms sometimes. Stop trying to shake my hand all the time.

Soul Crushing Questions FactsYouTube

16. It Is Tough When Your Friends Don’t Like You

“Can you pass the ketchup?”

This was at a dinner date with a bunch of my friends after they had just planned an awesome trip together and asked everyone if they could come. They asked everybody but me.

It took a lot not to cry right there at the table. The worst part was that some of them kept looking at me because they saw what just happened but no one spoke up. I’m glad to say I’m not friends with any of them anymore but it’s tough when all your friends don’t like you.

Soul Crushing Questions FactsNorthwestern Mutual

15. This Can’t Be Your Home

Oh god, I got asked if my parents were home by a door-to-door salesman a few months ago. I’m 32.

Soul Crushing Questions Factsnytbas

14. Freelancing is Harder Than You Think

Great question.

I've spent 30 years building a career as a writer. Freelance work has become very lean since the recession and I've taken what I can get, including lots of product web descriptions and SEO.

The mom of one of my daughter's friends said to me one day "I'd like to go back to work and I was wondering if you thought I could do what you do with no previous experience?"

Yes. Dammit, the answer is yes. It sucks to work so hard for 30 years and find yourself back where you started. Copywriting is a commodity product.

Soul Crushing Questions FactsHNstyle - HNonline

13. Sometimes You Get Lost

When I was unemployed for a little while it seemed like everyone and their moms asked me “So, what do you do for a living?”


Soul Crushing Questions FactsLinguistics Research Digest

12. Finally Getting Noticed

"Have you been working out?"

Yes. Consistently for 10 years. Glad I'm finally getting visible results.

Soul Crushing Questions FactsFashionBeans

11. Do You Really Need to Ask?

People who saw my hair thinning for years and then ask me why I shaved my head. Come on, did you just want to hear me say it?

Soul Crushing Questions FactsYouTube

10. Growing Into Yourself

When I was about 13 I overheard a little girl ask her mom about me. "Is that person a boy or girl, mommy?" I was devastated. I know she was just a little girl and that she wasn't trying to be mean but the fact she was so confused about me hurt. How could I possibly attract the opposite sex if they couldn't tell I was a male? When I was 13 I was a chubby guy with long hair that went past my shoulders. Now, I'm a bearded, short-haired man that has lost some weight and is OBVIOUSLY A BOY.

Soul Crushing Questions FactsHair to stare at

9. Alzheimer’s Sucks

My grandfather had Alzheimer's and it was progressively getting worse and worse. Every time we would go over to my grandparents' house we could tell he knew we were important but never really remembered who we were. So every time we went we reintroduced ourselves and who we were to him.

One day, before it got really bad, he was walking around and just looking at us (me, my mom, and my sisters) and he stopped, grabbed my hand and asked, "I'm supposed to remember you. Why can't I remember you?" I had to smile and tell him it's okay but my heart completely broke. This disease sucks.

Soul Crushing Questions FactsHelp For Alzheimers Families

8. Teenagers Can Be Mean

I was 15 or 16 at the time. But I was walking down a hall in high school and one of my cousins was up ahead talking to an acquaintance of mine.

They don't see me walking as they are at the lockers.

First thing I hear is "[That person] is your cousin!?! Ewww, I'm so sorry for you". She realized shortly after that I was standing behind her as she said it.

She looked at me, apologized, and didn't look at me again.

Soul Crushing Questions FactsTimetoast

7. Learning About Your Father

My aunt asked me, "Did you ever find out who your father is?"

I had no idea. That’s how I found out I'm only half as related to my brothers and sisters as I thought. And I'm not related to my dad at all, but he raised me and he loves me and I love him. I don't know who my "real" father is/was, but I care; I just try not to show it.

Soul Crushing Questions FactsYouTube

6. Family Problems Leaking Into School

"Why didn't you try harder?" Seems like something small, but this was asked to me by my then-English teacher when I was 15, when I “only” got a B+ on an essay.

I’d had less than five hours sleep during the whole week, my mom had run off to Cornwall in the middle of the night five days prior because she was stressed, leaving me to care for my 70-year-old terminally ill disabled father.

I'd written the essay during the early hours of the morning whilst also needing to be on call for my father who had just had an aggressive round of chemo and needed me to spoon feed him and hold his drinks so he could sip through a straw.

I literally fell to my knees in the hallway and burst into tears. My head of year (like a tutor) came to my rescue and sent me home. My mom came back that night after an angry phone call from a District Nurse about me.

Soul Crushing Questions FactsPhotos Public Domain

5. It Shouldn’t Matter

Everyone who has ever brought up my race/the fact that I’m mixed within the first three minutes of being introduced. I’m really ethnically ambiguous and I get that curiosity is natural but just once I’d love for it not to matter.

Soul Crushing Questions FactsNotey

4. The Guilt of Lying to Parents

It all started when I was young. I can't even remember how young I was, but I'm talking elementary/middle school age. I would go to school, do my thing, then come home. Like most kids, I had my backpack full of books. I couldn't wait to get home, throw that backpack in my room and then go ride my bike, or do something else.

I wasn't "against" school at that age, nor did I have a hard time learning, but I did have a problem with sitting down and doing boring stuff. At night, my parents would ask me if I had gotten my homework done. After spending the whole day in school, the last thing I wanted to do was more work, so I would tell them "yes."

The next day would roll around and I would rush to get my work done on the bus, and typically would have great success in doing that. However, that didn't always happen. When I didn't get my work done, the teacher would go around and collect assignments and ask "did you get your homework done?" Immediately, with a quick rush of blood flowing to my face I had to look at the teacher and say "No" but inside, I felt so guilty that I not only didn't complete my homework, but I lied to my parents about doing it.

Soul Crushing Questions

3. Remembering Mom

My mom died a couple weeks before I got engaged. Went dress shopping with my bridesmaids a couple months later. I found the dress I liked and the sales girl goes "Did you want to buy it now, or did you want to bring your mom in to see it first?" Everyone just froze as I muttered, "I' it now...thanks..."

Soul Crushing Questions FactsRole Reboot

2. Question of Kids

"How many kids do you have?"

I lost my oldest son a few years ago, whenever people ask how many children I have trouble answering. Usually, I just say I have one because I don't want to confuse people. I always feel bad saying one because it makes it seem like my first was never here, and he was.


1. Last Words From Grandma

My grandma had quite bad Alzheimer's by the time she died and didn't recognize me or any of my cousins anymore. When we got the chance to go and see her (this was like a once-every-few-years occurrence since we lived in different continents), she told my brother he was a lovely, handsome young man and asked to hold his hand.

Then she looked at me, with genuine concern, and said, "Is your face okay?"

It was super well-meaning and it didn't bother me at the time, but I was a bit crushed later that the last thing I remembered her saying to me before she died was a comment on my acne. But hey, I guess there's something to be said for the fact that she still cared about my well-being, even though I was essentially a stranger to her at this point.

Soul Crushing Questions


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