> That's a recipe for women to feel creeped out.

Countless surveys have shown that women do want to be approached. And don't forget about the "Brad Pitt vs Stalker" duality that exists for women and dating: They either view you as handsome who can do no wrong (including approaching them at Meetups), or some kind of creep. There is little in-between. Also, women view about 80% of men as unattractive. It is not a normal distribution, as men rate women's attractiveness. The open secret is that you need to approach lots of women on a regular basis in all sorts of different settings. Eventually, you will find luck.