What would you do?

I am interested in a military man who is divorced and three years older than me. He has a son who's 3 or 4. We used to live in the same duplex , him on one side me on the other along with a whole lot of my other friends. So we've known each other for five years. I like him but one of my best friends likes him too. The man has expressed that he likes hanging out with me. We hung out for four hours last Saturday night. He respected me and is very kind and polite.

So I'm in a glitch right now because I really want to talk to him but dont want to seem clingy. Should I message him at all? And if so what's the best thing to say when starting a text conversation?