A close friend asks--and genuinely wants--your opinion about something, but your opinion is one that he is likely to find quite painful. For example, your friend is an artist and asks your honest estimate of his chances of being successful. You think he is an atrocious artist who hasn't the slightest chance of success. What would you do?
If I were on the other side of this, I think I'd want my friend to be honest with me. If I suck at something, I'd rather a friend let me know about it than put myself out there and have everyone else in the world tell me I suck at it. So if it were me with the hurtful opinion, and that person asked for it, I'd give it. I'd find a way to be as nice about it as I could. Like, with the painter friend, I'd try to make it clear that even though he may not be able to figure out how to make green out of yellow and blue paint, I'd still support him any way that I could. You know, I'd still show up at art shows and what not. And honest opinions risk some feelings of resentment, but if the friendship is real, they'll get over it eventually. If they don't get over it, there's a good chance the relationship was shallow and wouldn't have lasted too long anyway.
*Question of the Week comes from The Book of Questions by Gregory Stock, Ph.D.