The Program: Step 1 - General Advice
Congratulations on making it this far! I'm going to give you some general advice, then you can try to figure out Your Problem.
As for some possibly useful information, I have two main points to make:
What Women Want
What's the difference? Being active, not passive. Even with the years of fighting for equal rights and the feminist movement, women want men who will take charge, be protective, and be strong. In a "perfect world" women and men would be equals in all aspects of the relationship...not to mention split the check and ask men on dates. This is not that world.
Do you know what else? That's okay! It just means that you need to learn the rules of the real world.
To quote from the movie Say Anything:
"Don't be a guy, be a man!"
The really strange thing is that it's a lot of fun being a man. A lot of work, but a lot of fun. And it's only fair that it's work. If she's going to work to look good (and how long does that makeup take?) the least we can do is plan the dates.
Part of this ability to be active rather than passive comes from having the awareness that as a Nice Man, one needs to be active. Where does the rest of the ability come from?
What is confidence? My footstool-sized Webster's New Universal Unabridged Dictionary defines it as:
Note how this compares to "shy," the curse of the Nice Guy.
Most women, as virtually any dating guide will tell you, are looking for a man who is confident and, in many ways, shy is anti-confident. Before you even think about dating, sit down and figure out what it is about yourself that you're confident about. Here are a couple to start with: first, you can treat women better than most jerks and second, you're smart enough to realize that you need dating help and you're making the effort to get it.
Okay, I know it's not much of a start, but it is a start. If you can't think of other things about yourself that you are confident about then you need to develop some before attempting to date. It doesn't particularily matter what it is that you're confident about: your abilities in martial-arts, dance, HTML coding, it doesn't really matter as long as there's something.
Speaking from personal experience, I can say that I used to worry about making a woman uncomfortable or offending her if I asked her out. This makes it sound like "wow, he's a nice guy to care so much about her feelings." Guess what. That wasn't it. It was a lack of confidence. When I ask a woman out now, I feel that, at the worst, she should take it as a compliment I'm a nice, intelligent, decent-looking, reasonably tall guy who can ballroom dance and gives good backrubs. If she's offended, it's her problem and I got out of the amateur therapy business years ago.
A Nice Guys reader, Jay, wrote in to comment on things that I needed to add and had some very good points that I missed:
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