re: Dating as a 40 Year Old Man, How Realistic is it?

Just talk to women you find attractive where ever you go. Smile, makes them laugh. Be gregarious.

If it's somewhere you'll both be often, strike up a conversation each time and build rapport, and after a few times get her number and see where it goes.

If you might not ever see her again, shoot your shot and try to see if she wants to go somewhere for coffee or whatever or at least get her number.

Don't get discouraged. Just keep at it. Don't be desperate, you'll reek of it.