I used to be apathetic to approaching women, and I still am to the extent that I don't pursue hard unless I get the rare oneitis. But I take small steps. What I've noticed is that almost every time I talk to any moderately attractive woman, cockblockers come out the woodwork to butt in, ranging from literally trying to push me out or kamikazing the whole set to being overtly friendly and conversational. The latter is a lot more common, and when I engage in conversing back (thinking I can show off my conversational skills), the girl gets radio silent or even leaves. I can think of sporadic examples going as far back as high school and college, and it's symbolic to every last woman. It's uncanny that you don't even notice them until they make their move, which is usually just to neutralize you.

I'm the type of guy who comes of as sociopathic I guess, but basically likable. People think well of me, but they overly apologize to me and are even afraid of me. This even goes back to when I was pacifistic and refused to defend myself. It's as if people are waiting for me to snap, so it's surprising that guys, even women, suddenly get some spine when it comes to me chatting up a woman. I'm starting to think I should just call them out on this, but they might use that as ammo that I'm breaking the PC wall (which I usually don't care about anyway, despite it's negative effect). Of course you can always ignore them (maybe), as long as you don't appear rattled. If there's a way to psyche yourself up beforehand anticipating things like this will happen, I haven't found it yet.