I’m not sure what to do. I used to date this girl some in High School and we also grew up together. We went in different directions after school and over the next 20 or so years when we would both come home to visit families we would sometimes get together. I’d say 3 or 4 times in 20 years. Recently we started exchanging e-mails and I ended up picking her up at the airport and giving her a ride home to see her family. We ended up going out one day on the water and she invited me over for dinner afterwards with her parents. I think she made a point to sit next to me at dinner as well. Did she do all of this to just be nice? Is she trying to tell me something, am I crazy? Or is she simply just wanting to see an old friend?
I’m torn of what to do next. Do I push the button and pursue this further or do I just sit back and take it as it comes as friends. The reason I ask this is because I feel that the entire time I have known her I have been hesitant to pursue her very much scared I would lose the friendship knowing good and well I wanted more. I have dated other women and was even married once and never have I been this hesitant/cautious as I am with her. To the point that I feel I have missed opportunities in the past because of it. This is a girl I have ALWAYS had a thing for most of my life and never could kick it. Spending this last weekend with her made me feel better than I have in a long time.
I feel like it is now or never and I do not want to miss another opportunity and want to roll the dice and see. I’m 40 and will be 41 in a few months she is 1 year younger than me. What to do?
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