People Break Down The Worst 'I Hate To Break It To You' Moments They've Experienced

No one likes a dreadful reality check. It can seem like the recipient is uninformed or naive.

However, nothing's worse than someone who doesn't just come right out and reveal the truth about a particular matter.

Instead, they dramatize the revelation with precursors like, "I hate to break it to you but..."

Curious to hear from those who were given major reality checks, Redditor ft-services asked:

"What's the worst 'I hate to break it to you' moment you had with someone?"

Relationships aren't always as they seem.

Catfished & Hung Out To Dry

"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."

– nothandomha

"Had a buddy who was head over heels for a girl he met online. They'd been chatting non-stop for months, and he was convinced she was 'the one.' He was about to wire her a large sum of money to help with some 'emergency.' "

"Something didn't sit right with me, so I did a reverse image search on her photos and found out they were stolen from a model's Instagram."

– kberryha

The Messenger

"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 [and dating website]."

"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."

– Chris

Whereabouts Unknown

"I work at a bank, and recently, one of my co-workers was helping a member trying to figure out what a charge was. It was for a salon, which neither her or her husband went to, coming from his card on a day when he was supposed to be on a business trip...."

"Edit: def wasn't stolen. Our system will tell us if a transaction happened online/POS/etc. It was with a card at the city's local salon, and the husband still had the card."

– eLlARiVeR

Nobody likes being the bearer of bad news.

Bad B.O.

"Having to tell people that they are literally smelling so bad they are excused from work to go home to shower and put on clean clothes. Then they can come back to work. More than once. To the same people."

– erkasaurousRexx

Color Correction

"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."

– IDriveLikeYourMom

"Had a colleague who was profoundly colour blind, and a boss who liked to run him about it endlessly. On said boss's last day, he asked my colleague how he found out he was colour-blind. My colleague explained the tests and pointed him at some online versions."

"My boss says 'hey, u/overkill, this test site is broken.' I go and check and it's working fine. It turns out my boss was also profoundly colour-blind, even more so than my colleague, just in a different set of colors. He'd never known, but it did explain his wildly clashing wardrobe. "

– overkill

Blind Optimism

"Having to tell 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."

– TeacherPatti

Necessary Evil

"I taught students with severe/profound needs for a few years. One of my students, who had an intellectual disability and severe epilepsy that could not be controlled by medication, was set on being in the military."

"All the staff encouraged it and would even set him up to chat with recruiters, knowing full well he could not be in the military."

"I pissed a lot of my aides off when I sat with him and had him research qualifications for joining the military. He understood how severe his epilepsy was, and that he could not be in the military with his epilepsy."

"He cried, but then he was able to move past it and picked an attainable goal. I even set him up with an internship at the local bike shop to pursue it."

"When I write IEPs, I ask students for their dream job and their back up plan. If they want to be musicians, singers, youtubers, football players, etc, I ask what they'll do to support themselves while pursuing those dreams. I definitely feel like the bad guy at times, but I feel like it's necessary."

– funparent

Warring Supervisors

"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 for what she did."

– wrludlow

These led to face-palming.

Clueless Investor

"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.'"

– miamoonof

Unqualified

"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."

– gaqua

"Funnily enough, I had the opposite experience with exactly the same type of guy."

"He was nice enough and got on well but incompetent. My boss and I decided to let him go and I was going to tell him after lunch."

"I was nervous as I was the one who had to do it, but I got back from lunch with an email from him saying he found another job and was leaving in 2 weeks."

"We cut him a cheque paying him out those two weeks and said goodbye that day."

"Conversation averted 😅"

– ZombieCyclist

It turns out that the bearer of bad news may actually be looking out for you.

You may not like what you hear, but isn't it better to know if you're being taken advantage of in a blissful moment of ignorance, or if you're not cut out to be in a position you're not well-suited for?

I hate to break it to you, but the truth hurts.

But we're all better off recovering from the shock and moving in a different direction towards a path that's right for us.