Okay for starters, I've been out of the dating game for a long while. I'm in my late thirties now, but when comes to girls I am still the same shy, unconfident kid I was when I was 13. In my few cases of dating/relationships, it's the girl who always made the first move. Even at my age I won't approach a woman first. Pretty pathetic.
I joined Facebook about a year ago or so. Someone I used to work with found me on there. Someone who I had secret crush on back then and of course I never said anything to anyone. But other than the friend request, we had no contact on Facebook over the year. Then a few weeks ago she sent me a message. She told me she remembered a funny moment with me many years ago at work. I replied it was good to hear from her and I remembered the moment as well. Then she replied back that maybe we could get together and catch up. I agreed. So we met up last week.
I was nervous as hell about the whole meeting few days leading up to our meeting. When I saw her, she looked great. Almost like I remembered, except she was more mature now. Dinner went well enough, I suppose. But I thought I left her with few awkward moments when I couldn't think about what to talk about. My problem was I was thinking way too much. But I must have done good enough, because she agreed to go for a drink. In all the evening lasted 4 and half hours. But I thought I tried too hard and worried too much about how I came across. We did have some good conversation. We had some good common interest like wine, music and films to name a few. But afterwards, I figured this would be it. It bothered me because I found I still liked her. Especially because she is different than anyone else I had gone out with. She is more reserved and quiet, but I know like me, she does come out of the shell when she is comfortable.
The next day I sent her a message on Facebook telling her I had a nice time and I hoped we could do it again. She responded and said she had fun too and would like to do it again soon. I replied and said I'm up for it whenever she is available. She replied how about this weekend. So at this point it looks like we will go out this weekend.
So all should be good so far, right? Not with me.
I understand this is only the second time out. I obviously have an interest in her. I figure she must have some interest in me to agree to a second time out. I'm not ahead of myself in anyway. It's a "let's see where this leads to" situation.
My problem is this. Myself. I fear I am going to ruin this. I don't see myself as some interesting enough, funny enough and even cool enough to win over a great girl. I fear I am going to trip myself up somewhere. I'm afraid I am going to freeze up on the date and be silent. I don't know how to make conversation when the pressure is on.
I know I have a funny side. I know I can carry a conversation. But when the pressure is on I can't come through. I hope I'm more relaxed this time and will do better.
Basically what I am getting at is, how should I go about this second time out? I think the first time was at first more like two old coworkers getting together. This second time I think it is more of a date. So how should I go about it?
