I think from 30 onwards it gets a lot clearer and easier

It unfortunately does not, lol. The caring about being rejected does, but other problems crop up, like meeting people in the first place.

For instance, I don't use apps, I don't frequent bars, and I don't want to get HR on my ass (everyone at my job is married or like 19 anyway). So where do I meet someone? Hobbies. Ok, well my hobbies are reading, walking around in the woods looking at cool nature stuff like frogs and salamanders, and going to (music) shows. Maybe I could meet someone at a show, but mostly it's loud and not conducive to conversation, and nobody wants to talk to strangers in a book store or library, and they'd rather meet a bear in the woods than me as we all know lmao.

Basically I haven't been doing this because I don't want to be creepy, but I'm thinking about just saying fuck it and throwing out a "hey you look cool, wanna go grab some coffee sometime?" just whenever, wherever the situation arises, and then get to know if I think she's amazing over time (if we continue, yadda yadda you know how it goes). I mean what else do I have left? And by whenever, wherever I don't just mean Shakira's hit, I mean anywhere, including but not limited to common places where it is often complained about like the grocery store, book store, where she works, just anywhere.

But yeah, anyway, things change when you get older, some things get easier but some get harder. Know where I used to meet women (well, girls)? School. And after that I had a stint in the bars. Back then I was afraid of the rejection sure but never questioned where to meet people. My flip has now flopped, however.