I think I would ask them how serious they are about this. It also depends on my motives for telling them, or for them asking me. Or vice versa.
The problem is that once I get started, I can’t be sure where I’ll end up. I will try not to be mean or obnoxious, but I can’t always tell what will bother a person. And then there’s the miscommunication problem. I was just telling someone today something that I thought about them—they didn’t ask; I just found myself going there. The last time I starting talking about feedback stuff, it got all upset-making. I think it was communication problems, but who knows? Maybe I was just being a jerk.
My preference is to be totally honest, and to have the same honesty shared back with me. However, I find that I often cushion things or tell white lies, and so I assume everyone else does, too. In essence, I don’t think total honesty is possible. I know people think it is, but I don’t think any of us knows completely what is going on in our heads. We can believe we are being honest while not being honest.
It’s all perception, anyway. Perception changes the world. If you ask for someone’s point of view, you can’t expect that it is the be-all and end-all. It’s just a point of view. If you rely on their point of view, then you deserve what you get, and what you get probably won’t be pretty.
Often, I believe, when we ask such questions, we are expecting to be told how fucked up we are, or hoping against hope we aren’t as fucked up as we thought. But maybe that’s just me, the perception of a sometimes depressed dude with low self-esteem, who always expects he is doing something wrong. I’ve learned not to ask that question very much.