August 28, 2023 | Miles Brucker

These Are The Most Insensitive Questions People Have Ever Asked

Life is full of questions—but some are probably better left unasked. To anyone with social skills, there are certain universally off-limit topics in casual conversation. Nevertheless, there are still people out there who either didn’t get the memo or just don’t seem to care. From the hilarious to the horrific, here are wild stories about the most insensitive questions that people have ever been asked.

1. So Much for Privacy Settings

I was interviewing for a big promotion at my old job. I had put in the time, the hours, and the effort for this promotion, and I had been passed up a few times, so I was sending out resumes while trying to get this promotion. I go through the first interview, and everything seemed great. They invited me for the second interview.

I was so excited. Flash forward two days, and I go in for the interview. The interview is with the regional and site managers. Everything is going great, they are asking me, "What are your priorities, goals, etc". At the end, the site manager changes his posture and says, "Would you say that you're a loyal employee"?

Taken aback, I say, of course, I've been here almost two years, etc. And like a shark circling his prey, this dude turns his computer monitor around and shows me my PRIVATE Facebook posts that I posted that I was in the market for a job in the same field. Now, there's no way he could have seen this, as it was a friends-only post. Someone I work with had to have tattled on me here. He then proceeded to read them to me out loud, not only the posts about my job search, but personal posts about my health situation and questions that I didn't bring up to anybody other than personal friends.

I look at the regional manager and this guy won't look me in the eyes, he is shifting, obviously uncomfortable.

I tried to say that I was looking just in case this promotion didn't work out, as I am a college student paying my way through school, but he kept interrupting me and saying, "Loyalty is key". He then tells me, "We will think about it," and points toward the door. The regional manager kind of coughs and goes to shake my hand, but by that point, I was already out the door.

So I said "Thanks anyway," and then proceed to have the most uncomfortable walk back to my desk—I was wearing heels for the first time in like a year so I stumbled on my way out the door—with coworkers asking for the details if I got the promotion. I didn't get the job.

I think the whole thing was just an "in your face" type deal.

I went on to get a promotion in a different department. I worked there for about another year and a half, and then I moved on to work for Netflix, actually. So, it all worked out!

That manager was unfortunately promoted to regional, but the replacement manager was much nicer and not a huge jerk.

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2. The Life of the Party

I got really excited one day back in high school when a friend of mine invited me to a party that one of the cool kids was hosting. I had always wanted a chance to hang out with that crowd, and was elated that I would finally get it. As soon as I walked in the door, one of the kids made a face and then asked me, “Who told you about this party?” in a way that made it very clear I was not wanted at this event.

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3. Pillow Talk

I caught my girlfriend of four years cheating on me. After a few weeks of hating myself, I decided to try and rebound with someone else. I ended up sleeping with a girl who always tried hitting on me while I was still in my relationship. While we were in bed together, she asked me, in what seemed to be a bizarre attempt at being flirty, “How does it feel knowing that someone who told you she loved you every night was doing this with someone else?”

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4. This Is Not the End

I broke my back when I was a teenager in an accident that left me paralyzed from the waist down. Shortly after the accident, this girl from my school decided to ask me: “So are you planning on ending your life some time soon?” Naturally, my response was “What? No. Why would I want to do that?” She responded by saying, “It's just that if I was in your situation, that’s what I would want to do…”

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5. What a Baby!

The most insensitive question that I have ever been asked as "Why didn't you just, like, have the baby?" This was asked of me by a friend the day after I told her that I’d had a miscarriage. Not only was this question extremely insensitive, it was also extremely stupid. I mean, honestly, how does she think this stuff works?

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6. Smile Though Your Heart Is Aching

When I was 16 years old, I got asked by some random male guest at my aunt's house if I knew that I was prettier when I wasn’t smiling. I’ve always been self conscious of my teeth, and this guy just made that so much worse with this question. I’m 28 now and I still hate my teeth, but now I will at least smile in some pictures.

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7. Cheat Code

“What did you do to cause that?” is the most insensitive question that I have ever been asked. It was posed to me by a female friend after I told her about how my ex-boyfriend had cheated on me. Can someone please explain to me why anyone would ever think that this might be an appropriate question to ask someone?

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8. A Terrible Decision

I was asked if I knew how much trouble I was putting people through by having cancer. Well, I'm so sorry that I woke up one day and decided that I wanted to have cancer just to inconvenience you! If I knew it wasn't going to be convenient for you to worry about me, then I absolutely would never have decided to jump on the cancer bandwagon!

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9. Hated and Lost

The most insensitive question that I have ever been asked is: “Are you going to make your sister's passing a national holiday?” This was because my sister had just passed at the age of 43, marking the first significant loss that I had ever suffered in my life. It was the one year anniversary of her passing, and I knew it would be a hard day for me to get through, so I requested the day off from work.

When word got out around the office that I was taking the day off for that reason, a coworker asked me that question and then started bragging about how she could name so many people who she had lost over the years. Apparently, she had a brother who had passed at the age of 14, and she said she also knew about 30 other people who had passed since then. From that day on I absolutely hated her.

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10. Waiting on a Foe

I worked as a waiter for a few years back when I was in high school. On one occasion, an elderly gentleman came up to me and asked “Are you sure that it’s okay for you to be handling people’s food with all that acne on your face?” That was definitely the most insensitive question that I’ve ever been asked. Who talks like that??

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11. Did You Deserve to Hear That?

Shortly after I finally managed to get out of a horrific relationship once and for all after many years of trying, someone who I thought I could trust decided to ask me, “Do you really think that you deserve better than (insert name of ex here)?” Not sure that I will ever be able to look at that person the same way again…

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12. A Sick Thing to Do

When sitting my dad and stepmom down to tell them that I had been diagnosed with cancer, my stepmom’s immediate reaction was "Are you sure? You're always overly dramatic like your mother. She watched too many soap operas!" Yes, for real. That is really what she said. Needless to say, it was the most insensitive question I had ever been asked. But it got so much worse.

As if that wasn’t bad enough already, she then decided to start telling people that I didn't have cancer and that I had faked it. This continued throughout the many difficult months where I was undergoing treatment and a major surgery. Note that she and my dad were both there for this major surgery and all the treatments, so they clearly knew that I wasn’t faking it.

From that point on, at every family gathering, I was constantly asked, "Did you really fake cancer?" Seriously, what the heck?? Anyway, the good news is that I ultimately won my battle with cancer and I now choose to keep very limited contact with this woman due to her awful nature. The only reason I maintain even my minimal level of contact is for the sake of my siblings.

I have since confronted both my stepmom and my dad on the way they acted during that horrible period of my life, but they just act as if they don't remember any of it and don't know what I'm talking about. I've shown my medical records to my other family members to prove to them that I was telling the truth. They were all shocked. At least my biological mother supported me…

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13. When Size Does Matter

The most insensitive question that I’ve ever heard was when a guy I liked asked me, "Why is your chest so small?" Like, bruh! How do you ask someone that? Like, were you literally born yesterday? Are you not aware that people are extremely self-conscious about the way their bodies look? I honestly have no idea how people like this can exist...

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14. A Sick Request

I have a seizure-like disorder called chorea-athetosis. It’s a very unpleasant ailment that often presents itself in these really inconvenient episodes where I lose partial control of my body parts. One time, I was on a date with a dude. After I told him of my situation, he said, “Wow, it’d be pretty hot for you to have one of your seizures while we’re sleeping together. Do you think you could arrange that?” I didn’t bother with him again after that…

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15. Losing My Appetite

I’m of Indian descent and am currently dating a white dude from the Midwest. I made a delicious melted cheese appetizer for his family one Thanksgiving. After tasting it, one of his aunts told me, “That was so good! But next time, would it be possible for you to make us something that your people eat on Thanksgiving?” She said this with the emphasis and everything.

Umm, excuse me? I was born in this country. “My people” eat turkey and dressing for Thanksgiving. We just actually season it all, Karen.

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16. Misguided Guidance

I had a mandatory one-on-one meeting with my high school guidance counselor about college preparations and planning. The first thing he did when I walked into the room was scan me with his eyes and say, “Well, I guess we don’t need to worry about filing your college athletics form now, do we?” He then proceeded to put the form I came in there for (to swim in college) back in his desk.

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17. Loved Him as a Friend

"Why didn't you just date him?" was the most insensitive question that I’ve ever been asked. Now, it probably doesn’t sound too awful...but if you know the whole story, it's absolutely horrific. This was said to me by my best friend’s mother shortly after he had tragically taken his own life. He had a crush on me for a while and I loved him dearly...but I'm gay.

He wasn't going to be able to change that and he never really tried to, but his mom thinks he passed because I rejected him.

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18. Let’s Not Talk About Work

As a first responder, the most insensitive question that I get on a regular basis is, "So what’s the worst call that you've ever been on?" People constantly ask this as soon as they meet me and learn what I do. People, don't ask firefighters or paramedics this question. Don't ask nurses or doctors this question, either. Just stop it. Dealing with emergencies is a very difficult experience.

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19. Adopting a New Attitude

“Are you adopted?” is the most insensitive question that I have ever been asked. I’m an Asian female. I was working at a restaurant in college part-time and one of the white male customers just asked me that out of the blue one day, with no preamble or context. He explained that he was asking because “all Asian girls are adopted” in his experience.

I told him that I was not adopted after I got over my shock. Like, why on Earth would you ask a stranger that?? I wish I had been able to think of some witty comeback at the time.

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20. Two Days of Infamy

When I was nine years old, my best friend passed suddenly from a stroke. I was the one who brought her to the school office and stayed with her as the paramedics came to take her to the hospital. She passed four days later. It was an extremely difficult experience and caused a lot of pain and mental health issues for me over the next few years.

I eventually learned to cope by giving myself two specific days of the year devoted to thinking about her and letting myself feel my emotions fully. Those two days are her birthday and the anniversary of the day she passed. This is something very personal and emotionally significant for me, as you can no doubt imagine.

One day when I was in high school, I think around the age of 15 or 16 years old, I was hanging out with my friends at the local park. We were discussing what we were going to do the next day and I told them that it was the anniversary of my friend’s passing and that I might not go to school that day. Their response made my blood run cold. 

That's when one of my friends turned to me and sarcastically said, "So what are you gonna do? Sit around and mourn?" and then laughed like it was a joke. All I could say to that was, “Yeah, of course.” That was the first time I noticed that my friends didn't respect me like they did each other…I no longer hang out with them.

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21. A Hair-Raising Level of Insensitivity

I used to be a redhead. One time, in the middle of a big family reunion, my creepy uncle got super tipsy and decided to loudly ask me in front of everyone "Do the curtains match the carpet?" Being a young teenager, I had no idea what he meant by this. I told him that I didn’t understand, and he loudly replied, “What color is the hair on your privates?”

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22. Don’t Bring Innocent Passersby Into This!

My ethnic background is Hispanic. One time, an older coworker of mine saw a random Hispanic family walking by us and genuinely asked me whether they were my family. She was fully serious and totally oblivious to the fact that assuming something like that based solely on someone’s appearance is totally insensitive and ridiculous.

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23. A Weighty Issue

One time when I got back from the bathroom at a restaurant, my mom asked me in front of my entire family, “Do you go into the bathroom to throw up after you eat?” Ever since then, I’ve been feeling extremely self-conscious about my weight and I worry about everything that I eat. I’m not sure why she couldn’t tell that a question like that would be insensitive.

To clear up any confusion that people might have about this story, my mom has spent many years of my life telling me that I’m too skinny, that I don’t eat enough, etc. I think she is legitimately concerned for my well-being, but she has no idea how to handle that properly. I was borderline underweight for a long time because of an untreated thyroid condition.

Ever since that incident, my mom has been gaslighting me about the body shaming that she used to encourage in me and in the people around me. I have a complex about not going to the bathroom around mealtime now because I don’t want people to think I have an eating disorder when, in reality, I really just need to pee.

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24. What Was This Guy Thinking??

Soon after I got home from cremating my young child, someone actually had the gall to ask me if the cremation process leaves any chunks of bone intact and, if so, whether they grind them down or just leave them that way. Thankfully, I was able to see the humor in the situation and not lose my mind. This was probably helped by the fact that his wife looked like she wanted to ruin him.

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25. Three Square Meals a Day

In this case, it wasn’t so much the question itself that was insensitive, but rather the follow-up comment that came after it. My father-in-law once asked me if my husband and I were eating okay while we were away at college. My response was yes, that we were able to make ends meet and get groceries regularly while still having a little money left over.

He then said, “Yeah, I can tell that you've been eating plenty. It looks like you ate the whole darn grocery store!” I was 5'4 and weighed 110 pounds…

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26. Raining on His Parade

When I told my mother that I finally had a girlfriend, her reply chilled me to the bone. She said, "I recommend that you be very cautious of any girl who shows an interest in you. What do you really have to offer anyone? Not much to be honest." That was definitely the most insensitive thing that anyone has ever said to me, question or otherwise. Gee, thanks mom!

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27. Managing a Bad Situation

About three weeks after my brother passed, I went back to work. While I was there, this lady and her daughter came into the store. I had never seen them before in my life. She proceeded to introduce herself to me as a good friend of my mother’s. I had never heard her name before, nor seen her face, nor seen her at the funeral.

My manager was close by. She started to say how sorry she was to hear of my brother’s passing and started going on and on about it. I started getting upset. Then, a couple minutes later, my manager again starts to approach us. The lady then says, “Oh, by the way, how did your brother pass? I heard he took his own life. Is that true?”

I immediately froze up. My manager finally grabbed me and said to the lady, really angrily, “Excuse me, she's needed in the back, and if you're not going to buy anything you need to leave.” I turned around and walked to the stock room with tears running down my face. She was the best manager I ever had. Thank you, Johanna!

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28. Alternate Reality

The most insensitive question that I’ve ever been asked is “Don’t you find it weird that you’re gonna be a virgin for life?” Now, there’s nothing wrong with being a virgin for life, of course, but I’m not celibate. I’m just a lesbian. This comment was made to me by a straight boy who doesn’t believe lesbian intimacy is “real” intimacy.

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29. Not My Idea of a Joke...

I had a best friend pass in a freak camping accident. I was taking care of her cats at the time and, since her parents were completely distraught, I ended up taking care of most of the logistics of cleaning out her house, canceling out her graduate program of study, collecting stuff from her place of employment, etc.

I also helped coordinate the funeral and spoke at the wake. Because it was a friend and not a close family member, I couldn’t take much time off of work. As a result, I was back at work much sooner than I should have been. All of the faculty and staff I worked with were informed that I was going through some hardship, and mostly everyone kept their distance and acted professionally.

However, this one faculty member was horrible. He was a creep and had hit on me repeatedly. He came up to me one day and said something along the lines of: “So why do you stupid Americans go camping outdoors anyway?” while laughing. I was washing my lunch dishes in the public break room space at the time, and it was just the two of us.

Enraged, I closed my eyes and took a deep breath. Then, I slowly turned to him and calmly said that if he didn’t leave the room at that very moment, I couldn’t guarantee what I would or wouldn't do to him. I was so furious after hearing this that I had to leave work for the rest of the day. People can be the absolute worst sometimes, man.

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30. Movin’ out

The story of the most insensitive question that I have ever been asked happened back when I was in college. I had just learned that my sister back home had tried to take her own life. In a state of shock, I told my roommate what had happened. She immediately asked me whether my sister was a religious person, and then proceeded to explain that she probably did what she did because she was lacking religion in her life. She wasn’t my roommate for much longer after that…

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31. Language Barrier

Shortly after arriving in the United States for my new job, someone asked me "How was it having to learn a new language when you came here?" Bro, believe it or not, we actually speak English in New Zealand! Talk about being insensitive and stupid at the same time! That was certainly not the welcome I was expecting in my new country…

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32. Patching Things up

When I was serving in Afghanistan a while ago, we had an aircraft go down and lost several of our peers. Our unit was given a special memorial patch to remind us of the crew we lost. A couple of years later, someone back home saw my patch and came up to ask me where I got it and how he could get one like it. It started off innocent, but it took a dark turn.

I explained to him that the patch was made in memoriam for a specific group of people and was not commercially available. It wasn't his fault he didn't know, but I didn't want to talk about it so lightly. But then he continued asking how he could get his hands on that "cool patch." I literally did not know what to say at that point. It was a super awkward experience for me. After a while, it started to feel as if he was asking for mine…

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33. Taking out the Trash

In a middle school English class, a girl who would later become my friend once asked me the most insensitive question I have ever been asked. She said: “Hey, you don’t care about cleanliness, right? Can you get my pencil out of the trashcan for me?” Take a moment to try and imagine what a comment like that would do to a teenager’s self-esteem…

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34. Too Soon

The most insensitive question that I’ve ever been asked was, "You’re lucky! Now that your father is gone, you can finally have a life of your own. Are you going to have kids?" This was asked of me by an older cousin at my dad's wake. His newly deceased body was lying just a few feet away from us in a casket. No, I would much rather have my father alive than gone at 63 years old.

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35. Naming Names

I have a very unusual name that I’m fairly self-conscious about. I once went to a DMV office, and the lady behind the desk didn't believe that it was my real name. So, I showed her my driver’s license. She then asked me if I had changed my name to that as an attempt “to seem cool.” I angrily told her that I had done nothing of the sort.

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36. Table Talk

Large chested woman run in my family. I wear a size 30 G bra. If I'm wearing anything remotely form-fitting, I can't hide them. I don't like them and am actually on a waiting list for a reduction. 

Nevertheless, at a dinner party I threw a few months ago, the wife of a friend asked me whether they were implants. She asked me this as I was serving her food. In front of the whole table. There's no good way to answer that…

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37. This Little Piggy Went to Market

The most insensitive and awkward question that I’ve ever been asked is "Whose baby is that?" I was asked this while walking through a supermarket with my six-month-old adopted daughter, who is of a different skin color than myself. I suppose this person thought that I just went around stealing cute little kids and taking them shopping???

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38. A Game of Twenty Questions

My sister called to let me know that my grandmother had passed while I was at work. She had been ill for a while, but I still wasn't prepared for that news. She was the first person I was close to who I had ever lost. I went to talk to my boss about it so that I could go home and sit with my family to mourn. He showed me how much of a monster he was.

I told him what had happened...and then I had to sit in his office trying to hold back tears as he asked me a million and one follow-up questions. I was trying to answer sensibly until he decided to ask, "Were you even that close to her anyway?" I was utterly astounded. After I regained my composure, I immediately walked out of his office and headed straight to HR.

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39. Crossing the Border

The first time that I ever met my fiancée's aunt, she decided to bring up the fact that I was part Mexican. Her aunt's first question upon our introduction to one another was, "Are you in this country legally?" I answered her with my Pennsylvania accent, "Yeah, I was born in Delaware County, Pennsylvania. Just because my family background is Mexican doesn’t mean that I’m not an American..."

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40. Judging a Book by Its Cover

Someone I had just met once asked me, "Why are you gay?" Now, criticizing and questioning a stranger’s orientation is insensitive and rude enough as it is, but it’s even worse in this case: I am not, in fact, gay. I am, however, a fairly effeminate man, so my feelings of insecurity were not exactly helped by this comment...

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41. We’ve Got Your Back

The most insensitive question that I’ve ever received is “How can you possibly be bi? I would never want to be that!” This was said to me by a classmate during high school gym class. The two other dudes in my group freaked out at him so bad that he actually just left the class. It was cool that people actually stood up for me for once.

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42. Lost in Translation

I’m ethnically Chinese, but I was born and raised in the United States of America. Not only is English my first language, but I also study it in university. Nevertheless, someone I had just met once asked me, "How is your English so good?" I replied, "Well, I am an English major. Chances are, it's better than yours." He was dumbfounded.

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43. Bribery Will Get You Nowhere

The most insensitive question that I’ve ever been asked was by my mom, when she asked me: "What if you just sleep with a girl one time, just to see what it's like? You might like it! I'll even give you money if you do!" As a gay guy, hearing this question from her absolutely shocked me; and completely made me lose respect for my mom.

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44. Ethnic Stereotypes You Never Knew Existed!

I’m a young female from Lebanon. Recently, I was on a first date with a guy, which was going pretty well...until he decided to ask me, “So is it true that all Arab girls are secretly promiscuous?” When I asked him what he meant by that, he just said, “You know, my Saudi roommate told me about this. Is it true?” In this case, it was not true. He didn’t get a second date…

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45. Crossing Into Enemy Territory

My mother was born in Japan and my father was born in the United States. After mentioning that fact to someone I had just met, they asked me, “So if you were alive during WWII, which side would you have supported?” Right, because simultaneously making light of someone’s ethnicity and one of the most tragic periods in history is always a great idea…

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46. Bar None

The most insensitive question that I have ever been asked was, “Oh, so you want a Twithx?” I’m 30 years old now, but I grew up with a lisp. I was in speech therapy for years because of it. When I was about eight years old or so, I went up to a concession stand at my brother’s little league baseball game and asked to buy a Twix chocolate bar.

The teenage guy behind the counter, trying to impress his lady coworker, decided to repeat my words back to me and make fun of the way I had pronounced the word. It made me cry. But I got my revenge. This then turned into one of the only times in my life that I’ve ever seen my mom go into full “Momma Bear” mode. She asked me why I was upset.

When I told her what had happened, she marched up to that dinky little stand and tore the guy a new one. But yeah, that’s the first thing I always think of when it comes to insensitive questions or remarks. It’s weird how little things like that stick with you. Some people really suck in this world, but then you get to see the ones who don’t. Like my mom. Defender of the little people. Love her.

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47. Survivor’s Guilt

“You know your brother's passing is your fault, right?” That was by far the most insensitive question that I’ve ever been asked. It was asked of me by my mom. At the hospital. When I was six years old. We were in an accident and my brother had protected me. 

She blamed me for his passing for 11 years after that. Thankfully, I’ve gotten a lot of positive emotional support from people who care about me ever since. I only wish that I could somehow change my mother’s attitude, but I guess some people are just not cut out to be good people. I feel horrible about what happened to my brother and I owe my life to him, but none of that justifies anything.

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48. Your Money or Your Life

The most insensitive question I have ever been asked is “Why did you give him the money?” This question was asked by the manager at the store I used to work for, in response to me telling her that I had just gotten robbed at gunpoint during my shift. I guess a few bucks from our cash register was more important than my life, as far as she was concerned…

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Sources:  Reddit,



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