It's Not Complicated, It's Difficult

Man, it is always so much easier to give advice about love than it is to take it or act upon it. Why do we always complicate things to the nth degree even when we know better?

See, I have a friend who has been flirting with someone for a long time. I know the second person in a chatty sort of way. Now, the situation has been going on for a long time. My friend even got up the nerve to actually finagle a way around finding out if the other person was single. But the question that still needed answering was whether there was any interest.

I got bugged about chatting with the "love interest" in order to find out the answer. Felt a little silly but I wanted to help out. I had two choices since chat time was limited but outside events: 1) I could simply say hi and that my friend says hi too or 2) I could just come out and ask. Now, had I not known this person before, only option 1 would have been available. But since I do and time was limited, I went for it. Besides, any hinting I could have done would have let the cat out of the bag without ever answering the question. However, yes, there is an interest! And it wasn't feigned or anything. I happily told my friend that the pressure was off because we had an answer and no rejection was nigh.

So, what do you think happened?

Yup, my friend freaked. Now, I can understand a whole, "Oh my God I cannot believe you did that!" spiel. Yup, understandable. But it should help to know when another person has interest right?

Nope. I miscalculated how much communication anxiety my friend could actually get. I mean, I know nerves and have had them but today was major fear. I've been telling my friend all week that now is a good time to ask the interested party out. Nope. Michael thinks that the problem is that it's being done in too public an environment. That's probably partially it but I think phone would be too much to. (sigh) So now what? I don't know. I tried to help and made it worse and now I feel really bad about it. I mean, is there something I can do to fix this or do I just let my friend wallow in fear and misery? I am a little confused because they have known each other for a long time even though they have never been friends. I would have thought the familiarity would make things easier. But no. . .I want my friend to stop moping and take a chance. I thought it was time to but I guess I was wrong. But I wonder when the time will ever be right to pursue this dream? Any suggestions?