When I was about 16 I had a friendship with a boy who was really, really keen on me. I liked him because he was intelligent and nice but didn't fancy him and was keener on 'bad boys' and eventually went off with the local thug. That set a pattern and I have had many relationships with unsuitable men since (and one long 10 year relationship which just didn't work out). I am now in my 40's with an 8 year old DD.
I recently bumped into him again after about 25 years and we went out with some old, old friends and got on really well. It turns out we work near each other. He is now a solicitor and has 3 grown up children and is divorced. Since then we've been for lunch a few times. Although the chemistry is not really there for me in that I don't fancy him like mad, I don't I ever will fancy someone who isn't 'wrong' and that I need to grow up and I can see he is still kind, lovely and intelligent.
But I don't know if he is interested in me anymore or how to make it clear that I might be. I sent him a text suggesting an evening drink and he said yes and I replied and since then haven't heard back from him ( a few days ago). His phone coverage is very bad so possibly not received it but on the other hand he's not pursuing it himself. Not sure what to do as I don't want to chase him if he's not interested and when I see that he is still a nice, kind and gentle person I have regrets about the choices I've made.