Conversations you never want to have

1- I'm sorry you lost your little brother, his 6 week old baby is quite adorable
2- There are suspicions that your daughter may have an eating disorder
3- I think your boyfriend may be cheating on you
I engaged in the first conversation today, which I suppose is a good way to put the other ones in perspective. I have had the second one about 12 years ago with my friend's parents. I think they still think that I was fabricating it. I am not sure what they thought my motivation would have been. They assured me that if she had a disorder, her boyfriend would have let them know and taken care of her.
I think I have to have the third one.
I guess these awkward conversations are what prove your mettle as a friend. Who wants to prove themselves?