Should I Embark On This Relationship?

   As they say "every frog should know its goal" ..

   Love does not divide people into categories, otherwise it is not love, but accounting! Try and be yourself without worrying, if he falls in love, he has fallen in love with yourself!

   No one can know what will happen.

   Risk wins, risk loses!

   I think take a risk! And what does it mean that you are not in his category? If you mean social status, financial opportunities, as number 2 said, this is not love, but accounting. You sound smart and without knowing you, I think you're a decent and smart woman, so I don't see what might bother you. Act, otherwise one day you will regret and wonder what would have happened if she had tried. Braver!

   If you both want it - go bold! "Do what you have to do, and let what you want happen!"

   I think the maximum you can do is somehow subtly provoke him to act. Because otherwise he can very easily suspect you that you are mercantile and want it because of the money or the situation, without knowing the details, but this is the principle. And an intrusive woman is not the most attractive thing in the world. If you intrigue him, he will act on his own.

   As a woman who has been in a similar situation, but with some different details, I would say that if he has not done anything to get things done, he probably has no intention of doing so in the future. Of course, you can try, but I think the chance of being disappointed again is huge and just wasting your time, instead of meeting a new person to start over. The fact that he has been looking for you during these 5 years does not mean anything. He may have been lonely, he may have been bored ... all things that you don't want to be looked for. I wish you to find happiness!