“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.
#21
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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120points
#22

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.
117points
#23

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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112points
#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.
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.
111points
#25
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.'.
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109points
#26

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.
We had to tell her that we loved Niece but we weren’t going to be as involved as she was in the league.
103points
#27

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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100points
#28

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.
It was Valentines day, awkward.
98points
#29

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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95points
#30
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. .
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. .
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94points
#31

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.
92points
#32
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.
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.
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92points
#33
I explained to my girlfriend what hospice was and what it meant for her grandfather.
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92points
#34
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.
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.
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92points
#35
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.
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90points
#36
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.
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87points
#37
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.
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85points
#38

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….
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84points
#39

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.
My dad later told me that he fired that guy later that day due to poor performance despite multiple attempts to help him lol.
80points
#40
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.
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80points


