Hi Luke,
You asked why freeing yourself, just a little bit, would help your self-confidence.
Before I answer your question, did you notice your first assumption when I said "liberate yourself from conventional sexuality"? What did you assume I meant? You wrote "I don't see how dating ugly women will help my self-confidence."
Where did I say anything about dating ugly women. This is a knee-jerk reaction. Society and our media have programmed you so well (as they program all of us). I want you to think about this knee-jerk reaction, this false assumption. I want you to look at it from every angle, like a well-cut diamond. I want you to understand it from every side. I NEVER said anything about dating ugly women. You added that. It is an element of your mind that I want you to be extremely careful about.
I never said anything about dating ugly women. What I did say is that, despite what society tries to teach you, all people are beautiful. All I encouraged you to do was empower yourself by seeing the beauty in people - not date people society thinks are ugly to "build confidence."
Big difference. And a very telling assumption on your part. I date women society thinks are gorgeous, I date women society thinks are ugly. I think all people are beautiful... but I only date people whose persaonlities really turn me on. So how could that attitude help you? Why would that build your confidence?
This is the part where I answer your question. There are several reasons why liberating yourself from society's definitions of beauty will boost your confidence.
-You retake your ability to define beauty authentically. It is easier to pick up women you're authentically attracted to.
-You retake your ability to define YOURSELF as beautiful.
-You stop defining others as ugly
-You stop defining yourself as ugly. Therefore, huge confidence boost.
-Every conventionally beautiful girl becomes just another girl. Huge confidence boost as women who you used to think were beyond you aren't. You stop acting different around women who are conventionally beautiful.
-You see all others as beautiful, giving you a huge conversational advantage, and huge motivation to connect with other people.
-You throw away need to label others as ugly, and connect better with the world.
-You gain ability to find real beauty that others don't see. When you are with a person who behaves maturely, thoughtfully, you are always better off. Another confidence boost.
-You have rare wisdom and insight. This sets you apart.
-You have the confidence to overcome your insecurities. You stop needing to "prove" that you're cool by trying to make others jealous. You stop needing others to be impressed with the women you pick up. You do it for you, for them. Again, you stop allowing others to define success or happiness for you.
-Once you realize the REAL REASONS why you're beautiful, you can convince anybody you're compatible with.
I'm not saying all of these apply to you, I'm not saying all are available to right away. Some of these confidence boosts are available to you right now, without any prelude.
All this might not make sense right away either. That's normal, I invite you to think about it. It's the kind of thing that if you're not immediately persuaded, if you keep an open mind, you may see what I mean in about 3-6 months.
Izza