It feels like one slip up and it's GAME OVER son.

Reply too soon? game over

Reply too slowly? game over

Be too boring? game over

Be too edgy? game over

Escalate too quickly? game over

Escalate too slowly? game over

Be too needy? game over

Be too independent? game over

Tell her you prefer Red wine over white wine? game over

Issue is everyone has way different preferences and senses of humor and expectations, so it's not even obvious how they're going to respond.

But then at some point a girl goes from 'um, fuck off' to 'yes daddy' once you pass enough 'tests'? To think that a few errant comments or moves could mean the difference between you being some dickhead who tried to hit on them one night, to a guy who they're infatuated with and willing to excuse all sorts of shit behavior as you so often see in relationships also trips me out.

Is there any way to make it feel less frustrating?

Even when you 'stop giving a fuck' (which is impossible) it's still a headfuck, and it feels like you're walking on a minefield over thin ice