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Warning: Some sensitive material ahead.

Few things can ruin your day more than the need to have a tough conversation with someone. How will they react? How devastating is this news? Like it or not, sometimes we need to have these conversations. When there's a death in the family, people need to be notified. When someone is gravely ill, loved ones need to be told. If someone you love is hurting themselves in some way and needs an intervention of some kind, then a decision might need to be made there too.

People told us all about their experiences after Redditor batting_1000 asked the online community,

"What's the toughest conversation you've ever had to have with someone?"

"I was a teen."

"Translating for my father at his last chemo meeting. "The cancer has spread, they're stopping chemo." I was a teen.


I am sorry for your loss.

I must say: That is wrong. This is what professional translators do for a living. To place that burden on a teenager is inappropriate.

"I had to be the one..."

"My best friend was killed by a drunk driver. I had to be the one to tell his family and friends, while still doing my job because I was the only manager available for the shift."


How does someone go to work after something like that? Sorry for your loss. Hopefully you've had better days since.

"I've never seen someone so sad..."

"My uncle was in chemo and passed away later in the day. I worked nearby and was the first person to get to the hospital in response to a "complication." Telling my mom he passed away was hard, but the hardest call was to my grandma. She'd spent the previous year in the hospital with him, and that woman aged 10 years in about 30 minutes. I've never seen anyone so sad and defeated."


"Her cancer had spread..."

"Telling my wife we were going to remove her oxygen. Her cancer had spread and there wasn't anything left we could do. She looked at me with such sadness. It's seared into my brain. Then, a few days later, I had to tell my 4-year-old his mother died. Watching his face trying to comprehend what I just said broke my heart. It hasn't even been 2 years yet. Worst couple of days I have ever experienced. I miss her so much."


"Hearing my cousin tell me..."

"Hearing my cousin tell me that he had been a freelance hitman in a bad part of Johannesburg for three years and that's why we lost contact. I thought the gangs and drugs got him. He set the record straight that he only worked for money and no one else and that he was done with it because he had his first son."


Johannesburg is rough. Without a doubt.

"Young kid died..."

"I used to be a deputy sheriff. Young kid died in a motorcycle accident. Went to his house at 9 AM on a Sunday morning. Interrupted the entire family and extended family who are sitting down for Sunday breakfast and then were on their way to church. A good 10 people. I had to tell his father that his son died right down the road from his house. The whole family erupted into screams understandably. That sticks with me."


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I do not envy the job of a sheriff or officer. Situations like that are too much for me. Much respect.

"He has never cried..."

"Telling my dad that his brother died.

Seeing him come home in tears is something I will never forget.

He has never cried in front of anyone so seeing him break down like that was something... scary."


Witnessing our parents break down is frightening. We're so used to seeing them as pillars of strength that when we see them crack, it can feel overwhelming.

"My brother died..."

"My brother died in tragic circumstances a week ago, and every day since somebody asks me what happened. It's emotionally exhausting."


"I had to terminate employment..."

"I had to terminate the employment of a single mom who was 8 months pregnant or so. She was laid off due to no fault of her own. She was a contractor, did great work, and we wanted to hire her, but it was on the front side of 2008; the company let all the contractors go. Zero I could do to change what was going to happen, but as her boss, it was my job was to let her know. Sucked."


"The hardest conversation..."

"The hardest conversation I've ever had was telling my wife and mother of my children that I was leaving her because her refusal to get help for her mental illness was destroying me and them. She checked herself into a mental hospital the next day. 6 years later and a huuuuge amount of effort and we're happy and together."


Unfortunately, we can't avoid moments like these. Life can sometimes be very painful and conversations like these might be warranted. The best you can do is commit to them––and be there for those you love.

Have some stories of your own? Feel free to tell us in the comments below!

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