How do you go about cultivating assertiveness with women? I attract a woman, date her a few times and at some point it always comes down to either I make some sort of move (kiss her etc) or it's done. I always feel like I need to ask permission to do so...you know how that ends. I DESPISE this and want to fix it... I just have no idea how.Let me explain by means of an analogy here. You're in a similar position to the guy who asks how to do a flip off the diving board who is afraid to jump off it. The problem is that no amount of coaching in proper diving technique is going to conquer the fear. The only way to conquer the fear is to be brave, which means doing what frightens you in the full knowledge that you're afraid. Until you have jumped off the board so many times that you become accustomed to it, your fear will prevent you from being able to pull off the flip.
Assertiveness comes naturally to some men, but not to most. So, it's usually a learned behavior, which is good news because it means that you can learn it. The first thing to do is to recognize your fear. When you start to tighten up and your heart begins to beat faster, that's a sign that you've triggered your fear. That's good, that's what you want. That's the point at which you have to simply jump off the board, trusting that the water will be there and that it won't hurt too much.
The great thing is that regardless of how it turns out, good or bad, it's almost never going to be anywhere nearly as bad as you feared. The monster in our imagination is almost always bigger than the real thing. So, test yourself. Each time you start tightening up and the fear begins to swell, do exactly the opposite of what will relieve the pressure. Every time you do this and successfully fight through the fear and act, you will reduce the amount of fear that will appear the next time. It will never disappear entirely, but it will become manageable and easily overcome.
And on a more specific note, never ask permission of a woman who doesn't have a material claim on you. She hasn't merited that right nor can you legitimately lay that responsibility on her. With women, it is almost always more effective to ask forgiveness than permission. And most of the time, since men are supposed to be the pursuers, she's waiting for you to make your move anyhow.