How would you handle this situation with a close friend?

I think I would just act normal, as if that situation didn’t happen. Keep talking to him as before and if he has completely stopped answering you, then give it a couple months and then stop contacting him. If he wants to contact you and talk about things, he knows how to find you. I know it’s hard to give up a friendship you are so invested in, but apparently, this conversation was not one he wanted to have with you and he felt you crossed the line.

Don’t push. It may already be too late. Your “acceptance” does not equal his willingness to talk about something. He probably feels pressured, like all you’re interested in now is forcing him to “unburden” himself about something that he very clearly does not wish to discuss.
Apologize, and mean it. Let him know you don’t expect him to be more intimate with his personal issues than he’s comfortable with. Then back off.

I would be very straightforward. Write him an old-fashioned pen and ink letter of apology that acknowledges that you crossed a line. Tell him you are very sorry, you miss him and you wish there were some way of picking up the friendship…on whatever terms.

Keep it short and simple.

A friendship such as you describe is very valuable. I would try to get it back in the same way as @gailcalled suggested; write to him, say you realize you had pushed a boundary and you miss the intimacy you once had. I hope you can get it back.

I think you have really created a climate for him to talk. If he had wanted to, he would of. It’s a fine line too, offering support, and trying to be a therapist to him, you know? So I would apologize and then respect him enough to leave that topic well alone.

How you approach him depends on his personality. You’ve been friends a long time. Was it a big surprise that he responded this way when you pressed him on the issue? Was it just a mistake on your part? Did you just kind of lose it with your curiosity?

Or were you really surprised? Did you think it would be fine? Did you think his reaction is unusual? Not him in some way?

Should you have known? That’s the question. If you should have known, then you owe him a big apology. Just explain you were curious and you let it get the better of your and you really want him to forgive you and rebuild your friendship.

If you couldn’t have known, then what has happened to him? Why did he change? I think you reach out to him and tell him you really value the friendship. You want him in your life. You don’t understand what you did wrong. Could he please help you understand?

Now it may be that he has written you off and there is nothing you can say at this point. If that’s the case, you may want to ask him straight out if that’s what he wants, because you don’t want to waste more time pursuing him if he has no interest in friendship. That’s not fair to you. So ask him to give it to you straight. And if he hasn’t written you off, then be strong about figuring out how to fix the relationship.

Thank you all for your advice. Sorry about the delay in the reply, technical difficulties I have decided I will send a brief apology, that I miss him and consider his friendship valuable and hate that I have done something to jeopardize it in any way.

I suppose the problem, @wundayatta is that I didn’t think. I was just frustrated. Our friendship feels unequal in that I can share more then he can because this issue is big enough that it reflects on almost every aspect of his life.

We still do talk about things and ideas subjects that interest us etc, So I have sort of justified continuing to have him play the confidante role. And when I hesitate he always assures me it’s OK and he’s interested. But really I am not completely comfortable in an unequal role. Also I can hear his depression about it and I don’t think he talks to anyone else so it hurts me that he is hurting and doesn’t trust me enough to open up. We can talk about it through the back door it seems or indirectly infer to it but that leaves me wondering where he has his boundaries, at what point he will shut down

There was a time when I was judgmental about it, I moved from judgmental to curious and was inquisitive about it, he usually did shut down in a similar fashion but not in a lasting sense. As I changed from inquisitive to just acceptance I figured actions will speak louder then words. He will be able to sense a change in me and be able to be more genuine. But I wonder when he hears me talking if all I am conveying is uncomfortableness, not knowing that it actually stems from me not knowing where his boundary is.

As a person I find myself less inclined to drama and confusion due to misinformation or lack of information. To be succinct I am much more direct. I realize not everyone understands this and there are some issues that require a lighter touch, but since that wasn’t getting me anywhere in this situation, I later justified my seemingly unplanned You know we can talk about this if it is bothering you. I haven’t always been a good friend about this but I did eventually come to accept you a long time ago, just never figured out a way to tell you, but I also understand that it affects your life and you seem depressed, if you ever want to talk about anything relating to this then lets talk, It may make you feel better. I may not have said exactly that, it was a while ago but that is gist and I can completely hear myself saying that. Understand that it probably came spewing out as if my tongue finally worked itself loose of censor I had it under.

So yeah I lack tact. But ultimately I agree. Even if does forgive me we are bound to go down the same road again. And while I will in different ways respect love and always think of him warmly and maybe always miss him, it really isn’t fair or healthy to either of us if we can’t get this issue straightened out.