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

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Just from reading, I think lack of confidence is your biggest weakness. Also likely more hookups come from the gym than anywhere. Hire a hot female trainer and start working out. Also puppies pull ton of tail.

Don't leave the bat on your shoulder, swing at every pitch. It you're out walking your puppy at the park and a nice looking woman walks by with her dog say, "nice looking lady you got there," if she replies, "it's a boy dog," you respond, "I was talking to the dog,"

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Confidence #1 for sure, also pushing yourself to just say hello and something nice when you are out and see an attractive (and age appropriate) woman. The goal shouldn't be to start a long conversation with every woman, but to get comfortable approaching women without being creepy or too awkward.

#2, location matters. If I was single and 40 I couldn't live in a small town full time, just lack of options, and opportunities. Not saying you have to move to NYC, but a larger metro, even in the suburbs, will provide more options.,