“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, and be sure to upvote the stories that resonate with you.
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….
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….
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.
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.”
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.
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.
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.
“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.”
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.
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. .
Share