I haven't tried this since I was 14, but I did meet girls then...

No sex though, because my grandma had me scared to death of getting a girl pregnant. Thank you grandma, I mean that.

Where does a 29 year old meet single girls in Springfield?

Are you planning to just walk up to women and ask them for dates?

No, I am too scared to do that, I would literally just think about doing it and going home and crying instead lol

But idk how any of this part of living works, I don't want to be creepy

Bars.

I never did the night life, my wife and I have been together since 17.

Maybe try online dating, take them to do something you like to do. Don't try to be someone you are not, you want to find someone compatible.