"I Still Cringe When I Think About This": People Are Revealing The Worst "I Hate To Break It To You" Moments They Had To Tell Someone, And They Range From Hilarious To Heartbreaking
Sometimes, when you're talking with someone, there may be a moment in the conversation where you have to tell them the truth about a situation that they got completely wrong. So when Reddit user u/floyd-96 asked: "What's the worst 'I hate to break it to you' moment you had with someone?" over four thousand people had hilarious yet frustrating stories to tell. Here's what they had to say below:
1."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 of 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 because they thought he was easygoing and cool to be around."
"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 one-on-one 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."
2."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."
3."I used to work in a customer care call center 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 and 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."
"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 she nor her husband went to, coming from his card on a day when he was supposed to be on a business trip..."
4."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. It was all completely wrong. I wrote the manual for it, I own the patent, and it's named after me."
5."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 two 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."
6."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.'"
7."My sister and her husband had a newborn baby. At four days old, my sister's husband turned to me and said, 'He'll sleep soon, right?'"
8."I had a friend ask me about some green sign in the distance. It was, in fact, a sodium vapor sign giving off an intense orange light, which sodium vapor is known for. I had to tell him right there that he was color-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."
"I had a colleague who was profoundly color-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 color-blind. My colleague explained the tests and pointed him to some online versions.
My boss said, 'Hey, u/overkill, this test site is broken.' I went and checked, and it was working fine. It turned out my boss was also profoundly color-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."
9."Not me, but my ex. A couple of years ago, he got a job as a cook at a big hospital. They had a mostly set and reoccurring cycle of dishes/items in Golden-Corral style stations around the cafeteria. Basic bitch food dressed up or pre-prepped. Nothing too fancy. During his first month, he became familiar with some of the residents and doctors who would make small talk and shoot the shit 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 food to take home."
"My partner's first time working at 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. My ex felt so sad he had to be the one to tell him."
10."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."
"On purpose? Was he shooting for a trifecta?"
"On purpose, yes. And yes."
11."My primary care doctor told me I have anxiety and exaggerated my health symptoms. I got to tell her I saw an endocrinologist on my own (luckily, with my insurance, I didn't require a referral) and was diagnosed with an autoimmune disorder."
12."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.'"
13."I was doing a phone port with AT&T, and when we got done, the AT&T guy said, 'Alright man, have a good weekend.' I replied back with, 'I hate to break it to you, bud, but it's only Tues....' I heard him actually sigh and say 'Fuck' under his breath."
Do you have an "I hate to break it to you" moment you want to share? Tell us what happened in the comments below.
