I've seen below average looking guys get girls

But then usually those below average guys are with below average women, By the way im no chad myself and I find myself attracted to a wide range of women although I do have a few preferences/dealbreakers.

I am initiating conversations with women and usually Id show my interest but not too much because I don't want to be seen as desperate. For example, id talk to a woman but if I notice that she isn't talking back to me much or isn't asking me questions back then that tells me that she isn't interested so I move on.

But then If I see a woman who catches my eye I think of things like "Is it the right time to approach her" , "Is her boyfriend near by" , "maybe she is a lesbian" , "How exactly do I open the conversation without making her think that I only want to have sex with her" etc.