My brother and I discussed this recently. Kinda older dudes in the hood seem to commonly appreciate skateboarding.
I've had randos film me without asking at this shitty bank spot by a park. They just come up (usually wearing Brixton or RVCA) and say "Dude that was sweet (high five), wanna see the clip I got?" It's a little corny, but I'd rather that than some irrational panic/"I'm calling the cops"
Side note: Common misconception that girls can be impressed by skateboarding, the reality is that 34 year old dudes in cargo shorts are impressed by skateboarding.