Question
I met a girl through my sister at the end of 2005. Six months later I met her again and really fell for her. She's a couple of years older than I am and at that time had just come out of a long-term relationship. I tried asking her out, but made a mess of it. I met her at the wrong time and was a bit full on. Later I tried to make amends by saying sorry for my brashness in a nice letter, but never got a reply.
I fell in love with this woman. Yet two years later I met her again, but we barely said hello to each other. It was at a party. In spite of all that, I still think about her every day. I know I need to move on but can't get her out of my head. I feel I blew my chance with her and regret that terribly. She's going out with someone else now, and may well announce her engagement this Christmas. I don't even know if she was ever interested in me. It could be all in my head. Yet I felt I clicked with her in a way that's never happened me before, or since.
To be honest, I'd love to get another chance with her. Everybody gets a second chance. I feel I sold myself seriously short first time around. The odds, of course, are against me. Yet I think she's the one for me and I think it's worth another go. But I don't even know if she likes me. I have this gut feeling that she's going to break up with the guy she's now with and that that will be my chance. I don't want to make a fool of myself. This is doing my head in for the past five years. I wish life was simple and straight-forward.
Answer
The problem is not about making a fool of yourself. If something is worth it, then of course we take the chance of looking foolish. The problem is whether you're prepared to face reality, if it's put to you plainly. You haven't done so this far. You see I think you're right. I think this is all in your head. Deep down you know that. You just don't want to accept it.
You are a lonely man. Instead of tackling that loneliness you are day-dreaming. I'm not knocking the notion of day-dreaming as such - it is a gentle way of putting ourselves onto a higher plain when the going is tough. In your case, however, you're over-doing it. Dreams by definition transcend reality. But they can only be a break. Reality remains. With you, that reality has become wobbly. So let me spell it out. You don't actually know this woman at all. She doesn't know you. She's getting on with her life. You didn't make a mess of things some years ago. Whatever passed between you was so uneventful that it effectively didn't happen. It's just that you've created a whole story around a tiny incident.
In the process, by the way, you're putting yourself down. You're saying you got it wrong. You didn't. What you're getting wrong is to fantasise about some passing ship in the night, rather than tackling your shyness and isolation by looking around and seeing the people who could alleviate your loneliness. They are there. Get to know them, men and women. Get busy tackling life. And keep the day-dreams for the odd occasion.
