Why does a old friend that I used to date and is now married keep messaging me every single day and night?
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Clearly looking to have an affair. How to react to this is up to you.
block him, hes no good for his wife or you
He is wanting to cheat on his wife. If you were smart, you would block him. This is not going to end well, at all.
I guess go have a drink with him and find out. I mean, I don't like to encourage cheating but it sort of sounds as though neither of you is real happy.
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Tell him that you will forward future messages to his wife. Do not meet up: you could be part of a divorce.
I think it would be a bit premature to say that he likes you. He obviously enjoys your company and finds you attractive but this could be because he is frustrated in his current relationship. One thing we can conclude though is that this guy does not want to be with his wife. No man would say the things he does to you if he is happily married. In saying that, what I think you need to do is to let this guy know that eventually he will need to make a decision because he cannot keep spending as much time with you and make the comments that he does while being in a relationship - it is not fair for all parties concerned to go on living this way.