Why don’t I (f19) fall for guys I’m comfortable with instead of guys I find to be way cooler than me?

I'm definitely gonna sound like a jerk, which deep down I probably am, no matter how much I try to play the nice girl.

I'm kind of just ranting, I know that my issue is that with awkward, more socially inept guys, I feel socially superior so I feel like I can be myself without their perception of me really changing. But because I look down on them, I feel like I could never see them as romantic interests. I think a lot of this stems from me worrying about what other people think (mainly my family, most of which are very social and well-liked amongst their peers). But for me, even if I tell myself not to care about what other people think, I feel like that kind of judgement is ingrained so deeply in me that I just can't bring myself to have real feelings for my awkward guy friends.

That being said, I myself am SUPER awkward, and even though I know how to carry myself in environments with clear social rules (i.e. a restaurant, the workplace, etc.), in normal social situations I don't know what to do with myself. I think a lot of it is an inferiority complex, where I try to show as little of my real personality as possible so that people don't know what I'm actually like (kind of like keeping an air of mystery around who I am). But this just ends up with me projecting no personality at all, and I turn out to be really boring around people who I find 'cooler' than me. It's kind of the inverse of what happens with awkward guys. With 'popular' people I don't feel socially superior, so I feel like if I be myself, their perception of me will change for the worse.

And because of all this, two things have been happening. I've never been successful with anyone I have actual feelings for, and I've played a bunch of guys that I feel comfortable with because I trick myself into thinking that maybe I like them when that definitely isn't the case (which I learn after dating them).

So all in all, I feel like a terrible person who hurts people who really are important to me, and I'm stuck chasing after guys who have no interest in me. If I don't change up my mindset soon I'm gonna lose all of my friends and also end up alone forever. So please help! What should I do to stop thinking the way I do?