Without question, it was when my 2nd wife asked me permission to quit fighting for her life. We both knew she was exhausted and had no quality of life left and no hope of being made comfortable, much less well. She wanted my permission to die, and wanted me to let go. But it felt like I was betraying her, even apart from my selfish desire not to see her die, and even understanding her suffering. Somehow I found the strength to release her, but that is hands down the hardest question I've ever been asked.
"Are you and mom ever going to get back together?" So much easier to tell everybody else, "Oh hell no!"
Intellectually? Probably the last of the final year practical questions in petrology, where they give you a bunch of hand samples, thin section microscope slides and a geological cross section and ask you to identify the rock types, minerals and their percentages and a summary of the geological history behind them. I'd run short of time and had about 10 minutes to do 30 minutes work.
Emotionally? Today my son asked me why he didn't have many friends. He's just started high school, has ADHD with some ASD traits and can be somewhat... intense. Hate to see him sad.
I totally understand about your son. My son is 28 now, but there were some rocky years as he was growing up. His father and I divorced when he was 4 and I was the only constant in his life. I married 2 more times and ended both of those terrible marriages largely because they didn't just not love my boy... they were actively mean to him. My son hated being different. He is super smart and funny but can still be very prickly. He has friends, now, and they understand his volatile moods. He has had girlfriends, but no one special and I hope someday he will find a girl who can see through the armor. All we can do is love them hard and be there when they need to talk. You can't fix it for them, much as you want to. Good luck. Know that you are not alone!
It appears it's going to be this one because there are hundreds of thousands of questions I've had to answer throughout my life and after arriving at this point, I don't remember which was which. What to do? What to do?
Never having had children, l was never faced with the really tough questions most of you have had to answer. I suppose the toughest was why l wanted out of a relationship. It has also been the most difficult response l have had to listen to when l have asked that same question. Not that tough compared to most, l guess.
Answering honestly when my son asked where his cat was when the cat had died the night before.
I can honestly think of two that may not be the absolute hardest but to the best of my memory they’re still up at the top haha.
I always think of Richard Feynman when asked "why?" Here is a link to a video to see how he thought about some "why" questions: