“Do you want the good news or the bad news first?” This is a difficult question to answer, because as soon as it’s been asked, your mind becomes flooded with potential “bad news” scenarios. And unfortunately, there’s never an easy way to deliver news that someone doesn’t want to hear.

Redditors have recently been recalling the most painful “I hate to break it to you” moments they’ve had with others, so we’ve gathered some of their uncomfortable stories below. Some of these tales might give you secondhand embarrassment, while others may break your heart. But they’re healthy reminders that we all have to deliver, and receive, unfortunate news at some point.

#1

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.

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.

Image credits: gaqua

#2

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.

Image credits: nothandomha

#3

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. .

Image credits: cpt_jerkface

#4

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.

Image credits: FingerSlamGrandpa

#5

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 credits: Longpork-Merchant

#6

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.

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.

#7

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.

Image credits: own_pleasure777

#8

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.

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.

Image credits: RareBeautyOnEtsy

#9

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.

Image credits: Cool-Newspapers

#10

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 credits: Goldf_sh4

#11

Freshman year of college a friend said that he was going to go barefoot as much as possible to toughen up his feet so that his future kids would be born with tough feet too. Had to explain to him why that wouldn’t work and the basics of genetics. He didn’t believe me and stuck with his theory. We have since lost touch but I know he had a son a few years ago. I’ll have to ask him if it worked out….

Image credits: Juxie

#12

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 credits: Lauraploradon

#13

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.

Image credits: kbrown423

#14

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.

We had to tell her that we loved Niece but we weren’t going to be as involved as she was in the league.

Image credits: Avocado-Toast-93

#15

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…

…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.

Image credits: ImNotRacistBuuuut

#16

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.

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.

Image credits: TeacherPatti

#17

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.

Image credits: Celefalas

#18

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.

Image credits: IDriveLikeYourMom

#19

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.

#20

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.

Image credits: fastfrank001

#21

A friend of mine unironically thought that he was the first person ever to experience existentialism- he literally said that no one ever talks about how small we are in the grand scope of the universe and kept saying that no one else ever wants to talk about the meaning of life ? i felt too bad to explain to him that the concept of how small we are in relation to our world has literally been one of the backbones of philosophy for centuries ?.

#22

Not me but I went to visit my dad at his job and he has an employee there who was kind of bragging to his other co workers about how well he has been doing at the job and thinking of asking for promotion.

My dad later told me that he fired that guy later that day due to poor performance despite multiple attempts to help him lol.

Image credits: swishymuffinzzz

#23

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.

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.

#24

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.  

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. :(.

#25

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

#26

Lol, I had to tell this girl that my boyfriend she was crushing on was… well, my boyfriend. She kept talking about how cute he was, and I was like, ‘I hate to break it to you, but he’s taken… by me.’ The awkward silence after that was priceless.

Image credits: CeceSmutt

#27

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 ?.

#28

I had been working on a project for about 10 months. It was finally done. I got to present it to my departments leadership. They loved it. I did a great job. They wanted to flow it up.

I ended up presenting to the president of the company. A highlight in my early career for sure.

I went and did the presentation, all 5 people in the chain of command between me and the president were there. Along with a lot of the other senior leadership in the company. The president seemed pleased with the presentation. I thought it was great.

We were apparently the last thing in the meeting so everyone was dismissed, then he asked me, my boss’s boss, and our Sr. Director to stay behind. He told us we did some great work on this, but to not continue any work, there was going to be a strategic shift and this project would not be finished.

Kinda stung, almost a year of my labor, a total waste.

Maybe unsurprisingly, about a month later there were layoffs. I took the buyout. I wasn’t feeling super secure in my position anymore.

#29

An employee confided 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.

#30

I was at a tech entrepreneurial meetup back in 2012. I spoke with one guy who was enthusiastically describing his billion dollar idea: an app that people at the gym could use to track their workouts and do challenges. He said there was even a social media potential because people could share their progress.

“You mean like Strava?” I asked, thinking he had perhaps identified a niche market not covered by Strava, Endomondo, and others.

I got a confused “What?” in response. He’d never heard of it. The look on his face when I showed him the app and he saw that his idea had been thoroughly realized for some time was tragic. How he had gotten as far with his idea as he had without finding any existing apps is a mystery to me.

#31

It’s always telling parents that their kid sucks at the sport they’re doing.

The parents drop and run and never see what the kids are doing at workouts and then when the kid gets cut from the top team they complain with s**t like “but I dropped them off 6 times a week for the whole season” and I hit them with the “I hate to break it to you but turning up is not the same as actually working out’.

#32

I once had to tell a friend that the “crypto expert” he hired was actually part of a pyramid scheme. He stared at me in silence for a few seconds before saying, “I already invested everything.

#33

I once had to tell a friend that the ‘homemade’ cookies she proudly brought to a party were just re-packaged store-bought ones we all recognized… The look on her face was priceless, but we still love her! ??.

#34

I had an employee who was a strict vegetarian for religious reasons. One day, we were discussing the employee salad bar and he mentioned how much he loved the Caesar dressing packets they offered. I was surprised and stupidly blurted out, “Oh, I didn’t realize you ate fish!” He responded that he was vegetarian and gave me a quizzical look. I had to explain that the salad dressing contained both fish and Parmesan cheese, which is almost always cultured with animal rennet. 

He didn’t believe me and, the next day, insisted on reading the ingredients on one of the packets to me to prove to me that I was wrong. Then he got to the anchovies and got quiet. 

I still feel awful that he had to find out that way. Neither of us handled the situation well. .

#35

My uncle called me to ask where my mom was. I told him she went to look at my grandfather’s body. Apparently he didn’t know his father had passed yet. That was pretty awkward.

#36

Sister’s a victim of her own impulsivity. She really likes new cars, and will roll negative equity into a new car. Then she’ll get bored of it, stop maintaining it, trade it in for a loss, and have an even bigger loan. And this was back when loans were pretty much free, and they could finance anybody.

So she called me up all excited because she found a new truck, got approved for financing, and was on the way to go buy it. So I went to meet her there, big V8 full size pickup truck. For a woman working part time and living in a congested city.

“Why do you want this?”

“My kids need a place to transport their bikes! And I want to go camping!”

So I test drove it with her, salesman was doing everything in his power to make the sale, and fair enough, he’s not a financial advisor, he doesn’t need to deal with the fall-out.

But right there in the showroom, I had to tell her that look, this is an awful idea, you can’t afford this. It’s going to be a huge burden on you, and you need to walk away.

Thankfully, she did. Salesman would have punched me if he could have gotten away with it, he was seething mad.

#37

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

#38

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.

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.

#39

Oof, I had to tell my friend her “designer” bag was a fake after she spent way too much on it. She had no clue, and I felt so bad breaking it to her, but I didn’t want her to keep bragging about it ?. Definitely an awkward moment!

#40

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….

#41

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.’.

#42

I was crossing the road at Great Portland Street when I heard a screeching of brakes. I turned around to see a dude flying through the air. It all happened in slow motion.

I got to him quickly and checked him over. He said, “I’m going skiing tomorrow.” I said ‘no, you’re not,” as I found the bottom half of his leg was snapped clean in half. Had to phone his wife and break the news.

#43

My brother calling me to tell me that our sister was in the hospital after a hit and run. Then hours later being told that she didn’t make it.

#44

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.

#45

I had to tell my friend that the girl he had been sexting was actually a guy friend of hers who was sharing screenshots with everyone on campus.

#46

3 friends and I applied to the same university. I remember that the day the results came out one of my friends was traveling and had no internet access. But we still communicated by pager. It was hard to tell my friend on his trip that he did not get into the university.

#47

Hate to break it to you, but you have been on the spectrum your whole life and nobody told you…..enjoy your 30s!

#48

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.

#49

My current Project manager

We’d been selecting a new software for almost a year and was in the meantime assorted to a more boring project.

After a year we’d finally kicked off and about a week in she took me into a meeting room apart.

“There’s been a merge, the project is called off”.

#50

A co-worker of mine doesn’t know the difference between type 1 and type 2 diabetes. My child has type 1, and he’s upset that “it’s a disease we created” and “will she grow out of it”

1. Type 2 is one that “*we created*” because people eat too much sugar (over simplifying)
2. No she won’t grow out of her pancreas not making insulin.

#51

Daughter of my mom’s closest friend. When she floated the idea of owning a dog, I told her that since she has dog allergy, she should not get any dogs. She proceeded to ignore the advice and get 3 dogs just because they are cute, one of them love to climb into her bed every night. After 3 years of complaining about headache, fatigue, constant runny nose and skin problems, I finally have a “I hate to break it to you moment” with her and she finally believed me and decided to give the dogs to her maid (it was a longer story than that, she first tested it by banishing that dog from her bedroom, then eventually restricting them to just the ground floor, and her symptoms keep improving after each attempt). Her symptoms vanished within 3 months.

#52

I was the one being “breaked” to.

In university, I was with a group of classmates and briefly ranted about how annoying it was when people recorded and posted countless, seemingly infinitely long video clips of concerts they attended.

Awkward silence, then two of the people there “jokingly” said they felt a bit personally attacked, chuckled and said something like “I want my friends to be able to see many different parts of the concerts.”

But I don’t regret anything. Stand for what I said and weren’t close to anyone there.

#53

Telling a girl, that was a friend of mine, that her new boyfriend, who was also a friend of mine.

Wasn’t attracted to her until she would lose weight. And his goal is to get you to lose weight. Cause he said he knows you’ll be knock out then.

She didn’t believe me.

A month later, she said she can’t believe it’s true, and wished she would have believed me. He left her cause he told her she wasn’t losing weight.

#54

When I had to tell my dad his cancer returned.

#55

Had to be the one to tell my wife that her favorite uncle died about 90 minutes before we walked down the aisle. She took it extremely well in the moment, but then it all sunk in a few hours later.