I have no issue with being myself, sitting in that awkwardness, teasing to establish a male-female frame, genuinely listening, building rapport, then setting something up based on what I want to do and what value I can offer to them as a mentor in their life and frame myself indirectly as a solution for (finding chinks in the armor and pointing them out, like: ignorance, insecurity, lack of life experience or adventure, fakeness, entitlement, unregulated emotions, missing a useful perspective or worldview, lacking someone non-judmental, indecisiveness, etc.). The only person this doesn't screen for is experienced fully-matured empaths (who are not someone you could date unless you have extremely high value other than EQ, and meet every criteria), or those types of women who want leverage and control in the relationship due to culture.

Anyways, my issue is creating the context to approach. What's a good rule of thumb? "I came to say hi because you looked cute" is on some high school shit ngl. You can succeed depending on your value and their personality since you're showing your intent but it's like you already gave up before you started. It needs to be obvious underneath the convo that it's man-to-women without it being overt. That's the most natural. You ever talk to a stranger and say "hi I came to talk to you because I want to be friends". I mean sure it works, but it's a noticeably strange thing to start off a convo with. It's like broadcasting "hey im low value, but im trying, please take care of me".

I know that you can try finding context in situation and going from there (ex. "what are you reading?"), but at times, that also comes off as unnatural in certain situations. I get a decent amount of IOIs in the hallway but can't conjure up a reasonable context to stop them. Or there's been times I see a chick looks vacant and I think of going up and saying in a joking way "what's on your mind? You seem vacant", but that catches someone off-guard and makes them guarded, for some. Any good actually decently socially calibrated ways to approach with context?