30 People Share Their Most Uncomfortable “I Hate To Break It To You” Conversations

Being the bearer of bad news is never easy. There are various scenarios where we have to deliver news to someone that they may not expect or want to hear. There’s even a risk that you may have to take the heat of the reaction as the messenger. Redditors recently recalled their most painful, “I hate to break it to you” moments. Scroll to check out the gallery below, where we’ve gathered a few of the most uncomfortable tales that may give you second-hand embarrassment or get you in those heartbroken feels.

#1 I had an upper management type guy try to explain to me, in a very condescending way, how a specific device works and how to install it. All completely wrong. I wrote the Manual for it....I own the patent...its named after me....

Image source: Longpork-Merchant, Antoni Shkraba / Pexels

#2 About a decade ago, I was having dinner with friends and we were all sharing crazy partying stories. One friend said that a few weeks before that, she witnessed a drunk girl chasing her crush around, frantically trying to kiss him or grope him. The poor guy kept telling her to stop, but she wouldn't have it. Some of the drunk girl's friends even joined in, they tried to undress the guy and would not let him leave. Eventually, the guy managed to escape and ran back to his car.

Image source: anon, Freepik My friend was telling that story as if we were supposed to laugh, but at one point, we gently broke it down to her that she had witnessed attempted r**e and the fact that the victim was a man was not an excuse. My friend's face changed as the horror of what she had seen dawned on her.

#3 My sister and her husband had a newborn baby. 4 days old. My sister's husband turned to me and said "he'll sleep soon, right?".

Image source: Goldf_sh4, Isaac Taylor / Pexels

#4 I hate to break it to you, but the hardest moment was telling my best friend that their partner was cheating. They were so in love and completely blinded by it, and when I broke the news, it shattered their world. It even strained our friendship for a while because sometimes, even when you're trying to help, the truth is too painful to accept.

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#5 My Primary Care Doctor who told me I have anxiety and exagerrate my health symptoms...when I got to tell her I saw an endocrinologist on my own (luckily with my insurance I didn't require a referral) and was diagnosed with an autoimmune disorder.

Image source: Elliejq88, freepik

#6 My sister in law. My niece plays field hockey and I love her. She plays in two different leagues. Meaning it’s 3 hours of field hockey games every Saturday and Sunday. My SIL expected me and my husband to drive an hour one way both days to watch niece play and pay rapt attention the whole time. Did I mention the games are at 7 am? We did this about once a month on either Saturday or Sunday and I guess this wasn’t enough for her.

Image source: Avocado-Toast-93, Luke Miller / Pexels We had to tell her that we loved Niece but we weren’t going to be as involved as she was in the league.

#7 I was doing a phone port with AT&T, and when we got done, the AT&T guy say "Alright man, have a good weekend", I replied back with "I hate to break it to you bud, but its only Tues....", I heard him actually sigh and say "f**k" under his breath....

Image source: Deiafter, Freepik

#8 There was a rule at my job where only one of these two supervisors could be off at a time. One of them loved to take a full week off work during holidays, to get more bang for his PTO buck.

Image source: wrludlow, Tima Miroshnichenko / Pexels One year, he had Thanksgiving week off, but the other supervisor had family come to town that week on late notice. The other supervisor asked him to cancel just one of his days so she could spend the day with family. He declined, even after she basically begged him, and he even said he didn't have anything to do that day... She then proceeded to take pto days every Wednesday of a holiday week for the next calendar year, effectively blocking him from taking his cheap weeks off. He told me that he thought it was funny because he knew she didn't have enough time to take all those vacation days off, and she'd eventually have to cancel some of them. I got to tell him, "I hate to break it to you, but she only took 2 hours off each of those days." See, the rule didn't differentiate between a partial or whole day, so she only had to burn 24 or so hours to block him. He looked devastated. It was kind of petty on both of their parts, but I give her credit for being creative in her retribution and don't blame her a bit for what she did.

#9 It’s part of my job but: Telling a couple their 15 day old had died overnight and was not able to be resuscitated. Those screams are a sound you can never scrub out of your brain.

Image source: cornisgood13, DC Studio / Freepik

#10 I have two. The first one was having to tell my father and my brother‘s girlfriend that my brother had been in a bad automobile accident, that my cousin who had been with him, was dead, and my brother was in a coma in a hospital three hours away.

Image source: RareBeautyOnEtsy, Yan Krukau / Pexels The second one was when I had to tell my mother that my sister was sleeping with my mother’s boyfriend. That was a tough one. And yes, I was 100% sure, because they did it in front of me.

#11 I was travelling for work in Australia. Let's say I was commuting between Perth and Sydney and back again. The back again flight was at stupid o clock, requiring me to get up at 3am to leave at 4am to be at the airport by 5am. I was groggy and moving on autopilot. I stopped to buy a coffee at an airport kiosk and the barista asked me ... where are you flying to today? I sleepily replied 'to Sydney' and the guy looked stunned. He said 'I hate to break it to you, but you ARE in Sydney.'.

Image source: Molloney178

#12 I had to tell my husband his ex-wife died. I felt so bad for him, but I assured him it’s okay to be sad and that he should attend her memorial.

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#13 Had to tell my mom, that my grandma (her mom) had died and been buried a month before. My mom had been in a Covid related coma for 6ish weeks during that time. At one point they were actually in the icu, in beds beside each other. Neither ever knew. Sooo yeah, that sucked.

Image source: Lauraploradon, Karolina Kaboompics / Pexels

#14 I used to work in a customer care call centre for a major telecommunications company. A woman called in one day to inquire about two 99$ charges on her bill from LavaLife. She kept pressing about the charges, what they were, and I had to explain to her that LavaLife is a dating service and that the charges were legitimate. If she didn't make them, did someone else live in her house who might have? There was only her husband, and I heard her go from '...But he would never...' to 'I have to go now' as it set in. That was almost 20 years ago now and I still feel awful about it. .

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#15 Oof, definitely the time I had to tell a friend that the business opportunity.... he was so excited about was actually a pyramid scheme. He was *so* hyped, talking about how he was going to quit his job and be his own boss. I tried to ease into it, but there’s really no soft way to say, Hey man, you’re about to lose a lot of money and ruin your friendships.

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#16 Fifteen years ago, my friend's father sadly passed away shortly after we graduated college. It was devastating for him. He figured he'd at least get a nice money boost to help him get back on his feet, but unfortunately, his father kept it a secret that he was deep deep in debt and had no liquid cash to his name. My friend had no support, and fell into a terrible depression. He was broke, he couch-crashed with me and our friends for a while, he quit his job...

Image source: ImNotRacistBuuuut, Laker / Pexels ...and he got comfortable with this new lifestyle. Two years later, he's still spending a month here and there with various friends around the city, eating their food, occupying their couch, sipping off their booze cabinet, using the terrible tragic passing of his father as his reasoning for being the way he was. It had been two years, we understood the pain he felt was real, but it was really time for him to actually get back on his feet and taking care of himself. We didn't know how to explain it to him, but we all felt he was taking advantage of us, and was using his father's death as an excuse to just not get a job. I found him a job. A nice one. One he would be good at, he went to school for, and didn't need prior work experience. I talked to a team lead and an HR rep, and got him a contact line for them, basically assuring an interview and a job offer if he arrived on time and sober. Weeks later, my HR rep and this team lead were confused, thinking I didn't relay the information to him. He never called. I gave him a layup of a job opportunity and he just ignored it outright. I called him out on it, but he told me to calm down and chill out, and that I wasn't being sensitive to his depression, and I wasn't understanding of his needs. So my worst "I hate to break it to you" moment...wasn't actually with him. It was with all my friends afterward. I had to tell them all to turn him down every time he asked to stay a week at their place. It sucked. The timing and my response to his refusal would give it away. This guy knew I was the horrible jerk who turned all his "friends" against him and denied him free room and board, hell I was probably going to be the sole reason he'd blame for his inevitable descent into homelessness. I accepted the burden, and called them up, explaining I had a job lined up for him and he refused, and we must all stop giving him a free place to stay if he won't take an easy job. Yes, it sucks his dad died. And it sucks he didn't get any kind of inheritance to start his life proper. It sucks he felt this terrible depression that lingered for years, and most of all, it sucks he had a group of enabling friends like me who humored it for so long it just became his accepted norm. We failed him. He didn't end up homeless, though. Without us offering his jobless butt a couch to crash on anymore, he ended up moving in with his aunt. Apparently she didn't take his excuses, didn't put up with his laziness, and did all the things we should've been doing all along. No booze allowed. No weed. No gaming after she went to bed. She only had one TV in the house and it was for Food Network only. He got a job developing 3d assets for VR titles, and started moving up and up creating VR Experiences for architecture companies. Dude still hates me probably, and I'll admit I made mistakes to justify it. But I'm really grateful his aunt was there. I did what I needed to do, but it would've been even 10-times worse if he did end up living on the streets, still blaming his father's sudden death for his two-decade-long predicament.

#17 Had a friend ask me about some green sign in the distance. It was in fact a sodium vapour sign giving off an intense orange light which sodium vapour is known for. Had to tell him right there that he was colour blind. He was in his mid thirties too. A lot of odd things that had happened in his past fell into place for him that day.

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#18 I explained to my girlfriend what hospice was and what it meant for her grandfather.

Image source: enocenip

#19 I had a guy working for me that was extremely nice, easy to get along with, and wildly inept. Not even like “low effort” but just…not capable of learning seemingly basic tasks. We tried everything. Coaching, giving him legitimate “checklist” instructions, having a team lead sit with him for a couple weeks to walk him through basics, everything.

Image source: gaqua, Tima Miroshnichenko / Pexels Everyone said the same thing. He just…couldn’t do the job. Everything he did had to be double checked by somebody else, which meant that we might as well have somebody else do it. But everyone liked the guy - they thought he was easy going and cool to be around, everything. But still he just straight up couldn’t do that job. So I had to find another place for him in the company that would better match his skills. The option would be for him to either take the lower job with lower pay, or he would be fired, with severance. I was not looking forward to the conversation. I called him in for a 1-1 to break it to him and the first thing he started with was “hey boss, before we start I just want to tell you that I really feel like I’ve been doing a great job here and I would like to talk about a raise.” Yeah, that conversation was not a fun one.

#20 I had to tell my friend that the online "girlfriend" he'd been talking to for months was actually a scammer using stolen photos. He was planning to send her money to come visit, and breaking the news to him was one of the toughest conversations I've ever had.

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#21 Having to tell a a student who was almost totally blind that she likely couldn't be an ER nurse. She and her dad moved to our district and at the IEP, her dad starts talking about how he can't wait for "Sue" to go to nursing school. I frantically scanned my brain, trying to think of how someone who was going to need Braille would be able to do that job. Then Sue piped up to say that her dream was to be an ER nurse.

Image source: TeacherPatti, Cedric Fauntleroy / Pexels Her prior district told her she could do anything, including this. She had a degenerative disease that would eventually make her blind. I talked to my friends who are nurses, I talked to our career lady at the school, I researched but there just wasn't any way someone who couldn't see could be an ER nurse. I reconvened the IEP and had to explain this. I know both were in denial but I was not happy that the prior district pumped up this idea. I mean, sure, there is lots she could still do but that just wasn't one of them. Then another student came from the same district with the idea she could be a CSI Investigator. She was also nearly blind.

#22 I told a gentleman with acute mesenteric ischemia that it was going to k*ll him. He told me that he’d had a good life, and if it was going to k*ll him in the next year or so, then he could accept that. I said, “this will k*ll you today, within the next 24 hours or so.”.

Image source: LifeApprentice, DC Studio / Freepik

#23 My friend has been constantly complaining about her husband. I visited them for a couple of weeks and I had to break to her that she is the problem, like massively so. I genuinely felt sorry for her husband by the time I left. The man gets both verbally and emotionally abused constantly. I told him he should report her to the police if she ever hit him again cause honestly, the situation is completely out of control. Even more out of control than she is, she needs a couple nights in jail to rethink her choices tbh.

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#24 I found out my friends girlfriend had Hep C. Her cousin told me she had it and she was not going to tell him. No one else would tell him so I called and told him. It was Valentines day, awkward.

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#25 My dad has been a musician since the 70s. He's incredibly talented, can play multiple instruments and has written many songs that honestly would sound at home on the radio.

Image source: Spacegod87, Chevanon Photography / Pexels About a year or so ago, some scam artist told him they "loved his work" and wanted to represent him and get his music out there to make money. They just needed a "small upfront fee"... My poor dad was so happy too. He had wanted this for literal decades, I think that's what clouded his judgement at the time. And yeah, the moment he told me, loud alarms went off in my head. I researched these people online and found an ocean of comments saying they all got scammed. I wanted my dad to be happy but I couldn't let him be scammed so I told him. He accepted it, kind of brushed it off...but it was that, "Yeah, I should've known this would happen." kind of response. Really depressing to see him so happy, just to be let down. I know to you and me this would have been an obvious scam, but my dad is from a different time and has no idea about computers or online culture. F**k scammers.

#26 An employee confidend in me that she contracted gonorrhea and was talking about how she got it from the toilet seat at work because she is monogamous with her husband. I was like girl he ain’t monogamous with you.

Image source: OkReflection4620, pch.vector / Freepik

#27 My best friend in high school was over weight and would sweat profusely. We would come in after lunch in Texas and he would smell awful. I think he would wear his clothes without washing them after sweating. We had english after and the ac sucked so teacher put a fun in the window. He would sit in front of the fan and blow his funk over everyone. The class got together and voted that I should be the one to tell him. Well I had to break it to him that for the last year he has smelled horribly. I felt pretty bad but he never stunk again.

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#28 When I got the call that my mom had passed they wouldn't say that she had passed, or that she had died, they kept saying medical things like, she doesn't have a pulse, she is not breathing, etc - it took a long time to understand that they were saying she was gone, and that it was final.

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#29 Not me but my Ex a couple years ago got a job as a cook working at a big Hospital. They had a mostly set and reoccurring cycle of dishes/ items in Golden-Corral style stations around the cafeteria. Basic b***h food dressed up or pre-prepped. Nothing too fancy.

Image source: Petty_Paw_Printz, cottonbro studio / Pexels His first month he became familiar with some of the Residents/ Doctors who would make small talk and shoot the s**t with him as he loaded up their plates. One of these Doctors was a man originally from India who was very enthusiastic about the Country Fried Chicken smothered in Pepper Gravy. He said it was his favorite dish out of anything else there and it wasn't uncommon for him to stop by at the end of his shift to purchase extra to take home. My Partner's first time working the Entree station the Doctor pointed and asked my Partner for his usual Country Fried Chicken. My Partner stared at him confused. They didn't serve Country fried chicken. But they *do* have Chicken Fried Steak. When he nonchalantly informed the Doctor of this, the man's eyes went wide, he looked genuinely shocked "This isn't chicken?!" My partner described the expression on his face as going from jarred and baffled to so, so sad when he realized he had been eating beef this entire time. But also that it had tasted so delicious. Apparently despite eating other types of meat, the man was still deeply tied to his Hindu roots and avoided Beef in his regular diet because of this. The previous cook before him had mistaken these ambiguous meat patties smothered in thick gravy for chicken so wires got crossed and he then relayed that incorrect information to the Doctor. I still cringe when I think about this. Ex felt so sad he had to be the one to tell him.

#30 Recently, a friend on Facebook mentioned how she was pro-life, but still thought women had the right to choose. I had to break it to her that if that’s her stance, she’s pro-choice. She deleted the post.

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