Back when I was a kid in HS I used to party a lot throughout the week (abusive household + somewhat lawless country) and sometimes I went clubbing still with my school uniform on and at least a couple of times I approached groups of visibly older women. Rejected both times but I’d like to believe my arrogance/confidence, which has helped me countless times, should be praised, lol.

That’s exactly why you could pull this off. Confidence.