But like others in the thread I do believe that practicing socialization will cause you to improve at it.
And at the same time people will think you're creepy and awkward if you "don't do it right", and if you tell them it's something you are consciously trying to improve on and you show them your written test cases, they might also think you're creepy and weird. One of society's non-rational double standards.
Luckily, it's entirely irrelevant. Simply not latching on assuages people's "creep" factor and besides, the idea is to get YOU to accept chatting not the other way around.
From my view:
/Ok ready? uhhhh ooooo here goes!/
Me: "Hey nice shoes."
You: "... thanks?"
/OMG I DID IT/
Me: "this is my stop, have a great day!"
/OMGEXCELLENTFINISHSOHAPPY/
From your view:
Me: "Hey nice shoes!"
You: "Thanks" (weirdo)...?
Me: "this is my stop, have a great day!"
You: /wow, ... i think he genuinely just wanted to give a compliment. didn't even try to bum money off me. huh./
...
point is - doesn't matter if they're confused or surprised you spoke to them. there's an assumption that if you speak up you must be out to manipulate them (sell something, convert someone, beg, etc.) and when you prove youre not, you help normalize ambient conversation AND fix your own sense of isolation.
This isn't entirely correct though. You definitely shouldn't creep people out or make them uncomfortable. Assuming no bad intent, it's still an issue to know that by saying something you could unintentionally make someone feel bad.
That's not to say that no one should ever say anything to an stranger, it's just to point out that there are non-zero consequences to your actions.
I think that depending on who you talk to they'll give more or less consequence to making someone feel uncomfortable. (I'm not strictly talking about dating or talking to someone you are possibly romantically interested in). Some specific extreme examples are: at work or if you are in a position of power over someone (you are their boss or their teacher)- or these situations there are more consequences to having an interaction where someone felt uncomfortable.
Yes, those are cherry-picked relationships, but just to say that fear of making people uncomfortable is a real and valid concern. Is your discomfort made up in your head? Many times it is.
Back to OP, relationships are complicated... it's not hard to see why people end up talking to AI bots instead.
(Same, not a personal attack, I'm interested in this subject and good to see it from different views).