asking older men about remarriage?

So he is the same personality that you dated ?

Don't fall into the same trap again or at least go very slow.

I was in that very same situation. When my wife and I divorced, I left her the house (many reason's why). About 2 years after divorce, she sent me a email with a house question. I knew this was a question she could have asked anyone, so I wrote back and ask how she was doing and things just took off from there. She used the house to break the ice, so maybe there is something you can use, if not, then tell him you just wanted to say hi.

If I were him I might be suspicious that you want to reconnect because I am in a good financial situation and you are not. If you really wanted to be with me because you loved me - you would not focus on marriage right away especially since you ended it last time.

Also if you are a spender and he is a saver and he has any sense he will "date" you but never marry you again.

>>>>>>>> I am 46 married 20 years and we are both very good with money so we have close to zero financial stress

I'm not an older man, but I believe that anyone who spends 20 years in a marriage with someone maintains a special place in their heart for them. If he is not currently married approach him about getting together for coffee or dinner to catch up. You don't have to make it an official offer. After that, just take it slow and follow his cues. Good luck!

I would want to be greeted with a smile and a nice hello. Maybe work it so you bump into him on the street, mall, etc., and then ask him if he would like to have dinner some time. His verbal and non-verbal response should tell you if he is glad to see you and if he is interested in getting together with you.