you sir sound like a buddy of mine he sorta has the same problem i once confronted him
NonStop: Hey man why do you always hit up on ugly chick? You can do better then that.
Scotty2Hotty: well i wont feel as bad when they reject me.
NonStop: Wouldnt that make it worst? i mean you just got rejected by an ugly chick.
Scotty2Hotty: Shut up man

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NonStop: hahaha that makes no sense at all.
the reason he said, is that he feels like its easyer to score and pick up ugly chicks, also he had a bad past experiance with a HB9 ex-g/f. He still an AFC and i got alot to teach him. I got him under my wing.
What i'm guessing is that you feels more comfortable hanging out with 6's but in the end you want more. the HB8 and 9 is out of your zone (or you think they are) You need to break out of your comfort zone. You have the game since you are picking up girls but you gotta raise your standards
What i do is i never rate a girl over 9 there all 7 and 8s to me and in my head i want a 9. So i go in already looking for a higher standard girl and just build up myself to that. Walk up to her think she will do anything to be with me .You.. my man you ARE the prize. Dont bring in the "What if's" in fact the "what if" dont exsist. When you doubt yourself is what hurts your game.