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Hello Victor!
I think that the men here might have some valuable insights to give you, but I wanted to share couple of thoughts that came to mind reading your post.
The problem with the PUA approach, entitlement in general and thoughts of an ideal relationship is that there might be a desire to cast people in particular roles, instead of allowing them to be human beings with free will.
Instead of looking at a woman as a potential mate first, what if you’d look at her as a brand new person that you can get to know? Would you be interested in getting to know people and what their interests, hopes and dreams are, without placing expectations on them? Curiosity is a great antidote for fear. It’s like exploring a new territory. Without the curiosity, what would be the point of going on an adventure, when you could just sit at home and be comfortable.
If you like Osho, then I’d recommend his “Intimacy: Trusting Oneself and the Other”. He talks about meeting another person just as you are and just as they are and how scary it can be, but how that is the essence of intimacy. You don’t want to desensitize yourself from other people (or be completely fearless). That’s not a way to have an intimate relationship. I know. I’ve done those mistakes! 🙂
Anyway, I’m sure that the men here can contribute in a way that someone who’s never been a young man never could 🙂