You are not insane... You are just wallowing in self-pity, defeatism, and self-disgust.
You say you want "this **** so I can possibly hook up with a decent reasonably young looking girl" and that is weak... You should do things only for yourself, do not seek to find success to please women. Instead find success for yourself, in doing such you become a stronger man and one that is more desirable to women. But make women secondary, the goal is not women but yourself.
Instead of wallowing and focusing on all the negative you instead need to focus on the positive and actively do something about it. You are talking about the past, but the past is just that... You need to move on from the negativity, you need to move on from the defeatism. Your mindset is toxic and you need to try to fix it.
Since high school what have you actually done to improve yourself? What are you doing now intead of wallowing here? You need to set goals in life, you need to work towards something, you need a purpose, you need to fight through the hard times and endure.
One thing... It is in our darkest moments and deepest pains that provide us the opportunity to grow stronger. It is then when you face yourself and you have to choose to either change it or to continue to suffer it. This moment of your suffering can be turned into a moment of clarity. Nobody here can help you... You can only help yourelf. You need to take control of your life.