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I don’t know the first thing about how to speak to a woman let alone ask her out.
I am a dating slub. I don’t know the first thing about how to speak to a woman let alone ask her out. I’ve watched my friends with different levels of success, but none of them have had what I call a successful relationship to a degree that I would emulate how they speak to a woman. As a result of watching all the failure around me, I have acquired some negative thoughts not only about men and dating but women and dating. I would like to find out about this whole thing myself, but I don’t know how to go about it. Can you help me break into the dating world?

I’m not sure how you acquired the negative thoughts about women and dating unless your pals are selecting women who are wrong for them, but no matter.
Your first step is to unlearn what you have learned so you can begin to discard your negative thoughts against dating. Your first step will be to speak to everyone. Just say hello to about twenty people, some women, some men. It doesn’t matter if they return the greeting, you need to get yourself used to people and the different way they respond.
After you can comfortably speak to all kinds of people, begin speaking to women. Again, keep the conversation casual and non-committal. You will begin to see women are different and will react differently to you. It doesn’t make them good or bad, it does tell you whether they are the type of woman you will want to date. You will get in touch with your own reactions to different women and you will begin to formulate your ideas on who you think best suits you.
After a few more weeks, you can begin to zone in on those women who interest you and make conversation that is non-threatening. If they are co-workers, ask a question about work and ease into asking them about themselves. You get the idea. Once you’ve established some friendships, you can move into the questions about going out for lunch and coffee and you’ll be on your way.
I wish I could tell you this will be smooth sailing, but it won’t be. But you will get an idea of how to maneuver the dating waters. If you need more specific instruction, don’t hesitate to write back.
Related Articles: How do you ask a girl out? I'm beginning to wonder if there's something inherently wrong with my strategy
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