Thanks, I may try to talk to passers-by more often and see where it goes, even just to excersize social skills my demographic seems to have missed. Honestly it feels these days like people in my age group (I’m 30) feel imposed upon by conversation but I too have seen others complaining about the same issue, so maybe I should “be the change I want to see in the world” lol.

Honestly as for the “creepy,” this may sound batshit insane but I’m not sure how much of it is really just in my own head. It’s not like I’m overtly sexual in my approach or anything (well again I haven’t really tried “my approach” yet either since I quit bars just before the pandemic, that is still so far theoretical), I’m looking for something long term if I can find the right person, I just feel creepy even trying to ask someone if they’d like to get to know eachother over coffee, and have no clue how I would get my proverbial foot in the door (something like your art gallery suggestion which I will likely use, I haven’t been to my city’s art museum in too long.) Once I get to talking to someone I think I can hold my own, I’m no [current male sex symbol] but I have jokes, a job, a house, and I look human enough, the hard part is really “hey.” It isn’t even the rejection that stops me, it’s straight up fear that I’ll be labeled creepy (and have to see this person ever again) or that I’m imposing and I don’t want to be an asshole and ruin some poor woman’s day by asking her out for coffee (which you see women complaining about all the time, but idk those dude’s sales pitch, maybe they’re really creepy about it and my pitch isn’t, or maybe they don’t try to lead with something like the art gallery, idfk, maybe all of that is just me overthinking because of crippling ADHD lol). Maybe you’re right, lead with talking about something in the surroundings, if she seems cool and receptive ask for a number/coffee date.

I know I rambled quite a bit, but tl;dr:

Thank you for the advice, I’m gonna try this for a while and see how it goes!