30 Excruciating ‘I Hate to Break It to You’ Moments

‘She thought she got it from a toilet seat…’
30 Excruciating ‘I Hate to Break It to You’ Moments

Every now and then, you have to tell someone a harsh truth instead of letting them remain oblivious. One Redditor, for example, had a friend who was constantly getting compared to Michael Scott. Having not seen The Office, this friend would tell people about the comparison, thinking it was a good thing. Eventually, the Redditor had to sit his friend down and play an episode or two, which obviously made his friend pretty sad to realize that being likened to Michael Scott is probably the first sign that you need to do some serious soul-searching. 

Other Redditors have remembered the times they had to be the bearer of bad news, and while it obviously hurt in the moment, all of these people are better off for now knowing the truth.

Dexican 2d ago I had a friend in college who had never watch The Office. Не would tell everyone that many people compared him to Michael Scott and he thought this was a good thing because well it seemed like Michael Scott was the main character and he thought main character = good. One day I just sat him down to finally watch the show and he got real sad. 45 Reply ...
gishlich 2d ago Not me but a friend had a band who got a singer who had a good voice but was not what the guitarist was looking for. So he let him go. Unfortunately it was during practice right after he showed them the tattoo the ex singer just got of the band name. 35 Reply ...
AdWorth4846 2d ago Had a guy at work confidently tell me that citrus fruits are all the same just picked at different times. That's why lemons on trees are green (limes) first. Не was heart broken to find out that grapefruit aren't just limes that got left on the tree the longest. 23 Reply ...
bitchyturtlewhispers 2d ago I'm an outdoor education instructor in Canada, but I work with a lot of Australian kids on holiday. I had one of them very sincerely tell me that Australia has the best music in the world. I asked who his favourite Aussie musician was. Не told me John Lennon. Unfortunately I had to break the news to him that not only is John Lennon not Aussie, neither are the other 3 Beatles. Не was not happy about it. 19 Reply ...
Deep-Beyond-2584 0 2d ago Used to work phones for Direct TV, a confused customer called in pretty upset because the NFL Sunday ticket was added to his account. Upset because he doesn't watch formal...when I went through the notes it said he has called in to add it a few weeks ago, not his wife, he got even more angry. Не said he was visiting his parents that weekend and only his wife was home. I think it clicked for both of us right away what had happened. His wife was cheating on him and the dude ordered football while
_ser_kay_ 2d ago My sister had already been having a godawful month when I had to wake her up to let her know her car window was smashed and the backpack she forgot in the car-with her laptop and wallet in it- was gone. 61 Reply ...
MaoriArcher 2d ago . I had a friend who complained about everyone and everything (assume about me also when I wasn't around). I asked him if he knew what the common denominator in all his scenarios were. We are no longer friends. 74 Reply ...
ControverseTrash . 2d ago When my sister was a teen she got pregnant. She tried to explain it like that: A sperm wandered across the bedsheet and into my vagina. We didn't have se*. I'm younger than her and still understood that she in fact had intercourse. + 79 Reply ...
classy_portuguesa445 . 2d ago 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! + 166 Reply ...
Deiafter 2d ago . 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 fuck under his breath.... 496 Reply ...
OkReflection4620 2d ago 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. 393 Reply ...
jelly_cute165 2d ago - 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. 464 Reply ...
poppyandsmall 2d ago A friend was really excited about a job opportunity. He'd been working hard for it and had all these dreams of what it would mean for his future. When he finally got the call, I had to be the one to break the news that the company had decided to go in a different direction. Seeing their face drop was heartbreaking. It felt so awkward, like I was the messenger of bad news in a moment they'd been looking forward to. 93 Reply ...
PenTestHer . 2d ago Had to tell a co-worker that his 'best friend' was working hard to get him fired. 87 Reply ...
fastfrank001 2d ago I I found out my friends girlfriend had Нер 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. 780 Reply ...
confusedmaybechemist 2d ago Edited 2d ago 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 629 Reply ...
Top-Cryptographer304 . 2d ago 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. + 571 Reply ...
RecognitionEast1278 2d ago 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. Не 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. + 1.5K Reply ...
miamoonof 2d ago I once had to tell a friend that the crypto expert he hired was actually part of a pyramid scheme. Не stared at me in silence for a few seconds before saying, I already invested everything. + 2.5K Reply ...
Cool-Newspapers 2d ago Oof, definitely the time I had to tell a friend that the business opportunity.... he was so excited about was actually a pyramid scheme. Не 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. + 7.2K Reply ...
CeceSmutt . 2d ago 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 + 3.7K Reply ...
Goldf_sh4 . 2d ago . 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? + 5.5K Reply ...
Juxie 2d ago 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. Не 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... + 4.3K Reply ...
ChicGirlVibes 2d ago . 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! 1.8K Reply ...
nothandomha 2d ago I had to tell my friend that the online girlfriend he'd been talking to for months was actually a scammer using stolen photos. Не 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. + 11K Reply ...
cpt_jerkface 2d ago 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
FingerSlamGrandpa 2d ago 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. Не 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
IDriveLikeYourMom 2d ago 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. Не was in his mid thirties too. A lot of odd things that had happened in his past fell into place for him that day. + 4.6K Reply ...
Longpork-Merchant 2d ago 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.... + 7.7K Reply ...
Rossum81 . 2d ago I work in criminal defense. More than once I've had to tell someone with a record as long as a Russian novel, a history of defaults, multiple open cases and serious charges that he's probably not getting personal recognizance or his charges dismissed. 50 Reply ...

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