Well, bro. Setting aside what others say about pickup; everything(including your career and women) depends on your mindset. I was virgin till 18 years old, but would have preferred a lot to be virgin than to fuck with a girl who cheated me afterwards with 3 guys(don't know how that happen, but it happen). The sex happened soon after I convince myself that I am worthy of everything. I convinced myself that I looked good, that I was perfect as who I am, and shouldn't compare with anyone else. My point is if you keep insisting that you are not a handsome guy, not intelligent nor valuable at all. You will end up earning what that person you've described will be. Perhaps, you fail sometimes, but that doesn't mean you have to give up. Don't be a quitter in your quest of self improvement. Perhaps, this may sound weird, but fake it until you make it. Act as the best image of yourself, and you will earn what the best of you should earn. Life is about choosing something, and focus on that something. If you keep focusing on what you are not("I don't have a lot going for me. I don't have the best-looking face or most fit body and I'm not the most intelligent guy in the world."), you will keep being in that. Good things come from inside out.\ Choose different.