My one grandmother I was very close to but she lived a long time (94 years) and she was generally very healthy. She suffered very little and went out on her own terms. I was probably the most broken up about that, but I got to spend the last weeks of her life with her and honestly if she was going to die, the whole thing couldn't have gone any better. And, of course, we're all going to die.

My other grandmother was a horrible, abusive person. My mom pretty well protected me from her, but her awfulness cast a long, broad shadow in everyone's life in our family. Apart from my mom having the weird feeling of being an orphan (her dad died way before I was born), I really didn't feel shit. I was almost happy. That sounds fucked up, but this woman was really vicious and cruel.

I had an uncle die and it was kind of like the OP's story. He was a nice enough guy from the little I knew but he had a lot of problems and he was hanging on by a thread for a while. Had serious diabetes and an addiction that made it a lot worse, a lot faster. It was very sad because in a lot of ways, he shortchanged himself in life. But in that sense his life was really sadder than his death. It felt like a release, for him and the people that worried about him.

Same thing with one of my best friends' dad. He was a really weird dude, though he did "cool" things like take us to the Forum for shows and leave his beer lying about. He was a major alcoholic, among other things. Once he led police on a chase for 15 miles with only three tires and ultimately only three wheels. Anyway, he died in pretty gruesome fashion and while I really felt for my friend, it wasn't my place to feel OK or not. But when I went to the funeral, it seemed like a lot of people in his family were just relieved that the call they were expecting finally came. It was kind of surreal.

The two times I have felt really bad and wanted to support the grieving parties, I pretty much came up empty.

I had a friend who died last year. He looked vaguely like me (of course much was made of this by our frat brothers) and while we were a lot different, we had things in common in college (mostly weed). Anyway, he had a lot of problems but he was a genuinely sweet kid who always seemed like he might be on the verge of turning his shit around. BANG, dead, 34 years old. I tried to reach out to his family, send them some messages and a lot of kosher food and later a card. Nothing. Not even a thank-you note. They were very conservative people, I guess they have been very guarded about the whole thing.

When I was in college my aunt got cancer and died. Then a year later, while his daughter was driving, her husband had a heart attack and died. I tried really hard to reach out to my cousin. She was a year younger than me, also in college. We knew each other well when we were young, like my parents were her godparents and all that. I felt terrible for her both times, but especially after she lost her dad because now she had no one. She became, maybe understandably, real withdrawn socially and from family for a while. She is a super successful person, I guess she just threw herself into her work. To this day, we really don't have a relationship. Maybe three years after it happened I finally talked to her about it and gave her a hug. It felt really empty. She dealt with it in her own way, I guess. Even now she is pretty strange, very much two different people outwardly and privately. I wish I could have done more but she managed to find the support she needed elsewhere, which is what matters.