I believe this is a fine line, and I often struggle to walk it

I’d be like this back in high school, low confidence, skinny af, and my interactions with girls would be

“Hmmm idk, whenever you say…. Oh ok ur late, no problem ☺️, oh u canceled! Oh see you next time then 😊, hmm idk hmmm where do you want to go to? Hmm ok whatever u say”

I’d be a nice guy, let people walk over me and not be firm enough

I kinda suffer from the opposite problem now

“Hey where do you live? Can I take you home?”

“Hey, let’s go grab a beer”

“I think you’re pretty, what’s your Instagram?”

And it sort of has worked a few times, but not always,

a friend told me “dude they’re not emotionally invested yet, and you hit them with a lot, “LET ME TAKE U HOME” “LETS GO GRAB A BEER”, you may be charming and look good but you’re still a stranger”

So where’s the line? Where do you give them agency and respect their space yet be direct with your intentions?

Do you say “Can I give you my Instagram?” Or does that sound passive and meek

Do you say “Are you free on Thursday? Let’s go out” or does that sound too aggressive?

Do you ask her when she’s free and accommodate yourself around her schedule? (Even if it’s not optimal) or do you give her a time and place?

Do you say “can I get your number?” or say “what’s your number?”

Does little wording like this even matter? Like is this a deal breaker?

One may be passive and needy but the other too aggressive and intense, where’s the line?