“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. Keep reading to find a conversation with the person who started this thread, Floyd-96 aka Screener on YouTube, and be sure to upvote the stories that resonate with you.
#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....
280points
#2
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....
268points
#3
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.
Sooo yeah, that sucked.
251points
To find out how this conversation started in the first place, we reached out to the Reddit user who started this thread, Floyd-96 aka Screener on YouTube. They were kind enough to have a chat with Bored Panda and share what inspired them to invite others to share their stories.
"Well, throughout my life, the society I grew up in had a major lack of honesty, or people were unable to confront someone about a sensitive matter with any degree of maturity or respect," the author noted. "The main cause of this question was actually a result of a philosophy of mine which was when someone says to you 'let me be frank', in most cases, they'll end up being disrespectful and/or emotionally expressive rather than being honest or helpful. It's almost like a phrase or a mask that people use when they want to express a very harsh or shocking opinion."
"A quick example would be if someone says to you, 'I hate to break it to you, but you're not funny,'" the OP explained. "What we consider funny, artistic, entertaining, etc. is purely subjective. It's not objective reality, so it is absolutely wrong to deliver a message with the setup that you're about to reveal a harsh objective reality to them, but in truth it's a subjective and personal thing."
#4
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.
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.
243points
#5
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.
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.
235points
#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.
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.
229points
"I mean if you look at history, many artists, musical artists for example, were told that they have no talent, they have nothing unique, their songs are terrible, they should stop pursuing their goals," Screener continued. "Most of the people who tell them these things are ones that I just described: ones who propose a personal opinion, a subjective take, but propose it as if it's an objective reality and you should surrender from pursuing your goals."
"Countless times these people have been wrong, which is why I came with the philosophy that you should absolutely not give a [crap] about anyone's criticism of your art form," the author says. "Pay no attention to critics, opinions, nothing, just do your thing without allowing anyone to interfere with your process or outcome. Once you do that, not only you win as an artist, but you become closer to achieving uniqueness and ultimately discovering your true self and who you are as an artist."
#7
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.
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.
205points
#8
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. .
That was almost 20 years ago now and I still feel awful about it. .
197points
#9
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.
I was like girl he ain’t monogamous with you.
191points
We also asked the OP if they believe that there's ever a good way to deliver bad news. "If humans had any level of decency, the scenarios would go something like this: so based on the previous example, if I had to confront someone who asked for an opinion, I would say, 'I don't think you're funny, but that's my opinion. Millions of people might find you funny, but not me. Do you think of yourself as funny? If yes, then stop giving a [crap] about other people's opinions and keep doing your thing, no matter how many people think of you as funny or unfunny. If what you do is truly unique, makes you happy and you grow as you do it, then do it for that sake, for your own sake!'"
#10
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.
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.
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179points
#11
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.
169points
#12
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?".
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165points
Finally, we asked Screener what they thought of the responses to their post. "I can see that most of the time people mean well, but they have a problem with delivering the message in a creative, civil or positive manner, thus using a socially manufactured phrase as a gateway to deliver news that they struggle to communicate in their own ways," they explained. "This question was simply a leaf from a branch belonging to a tree of philosophy that I'm growing, so I was simply conducting an experiment and the response was absolutely explosive & brilliant!"
#13
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.
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.
154points
#14
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.
148points
#15
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.
146points
#16
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.
144points
#17
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.
...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.
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137points
#18
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.
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.
128points
#19
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.”.
127points
