In this story, I was the insensitive one.
I was 24 when my Dad died, and my Mom instructed me to call my Grandfather (my Dad's Dad) and tell him. Since I had no experience in relaying bad news, I bungled it horribly.
I started the conversation by making small talk about the weather, and our recent move to Arizona. About 5 minutes or so into the conversation, I finally got brave enough to say, "oh, by the way, Dad died".
It did not go over well.
I have since learned the proper way to convey bad news.