I guess when you are middle aged (I am past that), then you have learned a lot over time. Whats the point of beating about the bush.
You are not a teenager anymore. If you fancy somebody, then go for it. life is too short. I guess safe sex is more important nowadays than it ever was. get him tested. If he is all clear, then within reason, you know he isn't a jump into bed with anybody, or he is just very lucky.
The middle aged bloke needs to sow his oats before it is too late. So be warned, he may not fancy you enough to get married to, he may just want sex.
At the end of the day it is your decision, you are a grown up person, who doesn't have to answer to anybody else.
I think life has changed dramatically. I don't think courtship comes into it anymore (blame telly and peoples morality and thepill and anything else that you can think of).
Hey at the end of the day, you have to decide, not anybody else.
Good luck on whatever you decide.