Originally Posted by
TheEvilJester
I see you asked for this thread to be deleted, so I am not sure if you are still looking for thoughts and advice. I will just say, though, 6 years is a LONG time. If you were interested in her, you really SHOULD have made a move. Don't get me wrong. Good GRAVY, I understand how you feel. In the past, I've always been so unsure of myself that I am quite sure I could have had a very similar story myself. I'd always been WAY too shy to know how to ask women out and WAY too certain they'd want nothing to do with me anyway.
So in NO way am I meaning to judge you. I'm just saying, if you were interested in her you should have said something a long time ago. You could certainly talk to your friend about it first since it is his sister. It COULD be a little awkward at first, but as long as you seriously cared for his sister and weren't just looking for a hook-up, I can't see why a good friend would be completely against it. He could be worried for what could happen if you two didn't work out, but I think if you seriously liked her, he'd probably be okay with it, if a little cautious.
It is certainly possible she was interested in you.... but again, the fact that you did nothing in 6 years of knowing her, and even more the interactions you describe at that wedding certainly seem to reinforce a perceived lack of interest on your part. So, even though it wasn't your intention, it sounds like you may have given her seemingly obviously signs that you are NOT interested in her as more than a friend. It MAY be too late now..... but it also may not.
The biggest mistake you made was in not giving it a try. Maybe now you still can. Even if it doesn't work out, even if she was never interested in you as more than a friend, or could have been in the past but it is too late now.... you are so much better of knowing that rather than being left wondering what if. On the other hand.... what if you give it a shot and she IS still interested? Wouldn't future you want to kick past you square in the nads for even thinking about not giving it a shot? LOL!
What if is a crappy question to have to live your life asking. Take it from a guy who has made similar mistakes way too much in life. To the point where, though I'll always leave a window open for love, I've grown to think it just won't happen for me. I've grown to think my chance at happiness lies in accepting that and adapting (for the record, it's been working very well for me lately, but is still a touch unfortunate how I had to come by that happiness). If you want love, you shouldn't have to share that fate with me. Learn to love and appreciate yourself enough so you don't NEED love.... but that doesn't mean you shouldn't search it out.
Good luck to you. I hope you find your dream girl very soon, whether it turns out to be her or somebody else entirely. But, more than anything, at least give yourself a chance. You deserve that.