What's the worst news you have had to deliver to someone?

That my Dad passed..

I had to tell an 8 year old girl that her father had passed away. Her mother couldn't do that herself. 😔

I had to tell my wife that her father had passed away. And more recently that our elder son had had a serious accident. I am still relieved though that I did not have to tell my sons of my wife's passing. They were with me at the time. As her passing was totally unexpected, having to phone family & friends was no fun.

I had to tell my parents that I failed my first semester of college, 12 years ago.

I was the ax man for this warehouse in Mount Vernon Washington that hired only non English speaking Hispanics. (Kind of shady) I had the unpleasant job of clocking them out and saying "Adios y bueno suerte." When they were "fired". Because they were being bused in and exploited by a shady contractor, this put them in a very bad position. Worse than a regular citizen being fired by a long shot.

I had to call a list of people to tell them that a relative had died.

Telling my mom her sister passed away because her niece couldn't do it.

A death, there's nothing worse.