Welcome aboard.
You'll have to overlook some of the posturing and flexing that goes on around here.
If you are a grown man who is still afraid of being direct with women, then there is something wrong with you.
If you've come here to make positive changes, then I'd say that "there's something right with you." It's the people that keep repeating the same mistakes and never wanting to improve... that have "something wrong with them."
The best "start up' advice I can offer is to think back to when you were a kid. If you wanted a favor from your folks, by trial and error... you eventually learned which one to ask .... you also learned how to ask ... and when to ask. Pretty soon, it became second nature.
The above principle also applies with women. Just like when you were a kid and trying to get something from your parents, sometimes you succeed and sometimes, you don't. When you didn't succeed, you learned to not make that mistake again and to try a different approach the next time. With women you will also experience 'trial and error' but instead of looking at it as "defeat" look at it as a learning experience.
With women, you don't really do as much "asking" but more 'guiding them' into your area of interest.
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I just read your above follow up. There's a fine line between coming across as insulting to women and being teasing and playful. There's an old saying... "it's not what you say, but how you say it." There's a lot of truth in that saying. Also keep in mind that if you are 'playing' with a woman that is full of herself, teasing her can deflate her overinflated opinion of herself. But... if you said the same thing to a girl that is not as self-assured, you might come across as being insensitive or insulting.
The more that you go out and try different approaches, the better you will become. It really is no different than when you were a kid and worked an angle on your folks to get the best outcome.
