How to Overcome Shyness Around Women – 5 Tips on Being Able to Confidently Talk to Women

Chris Tyler

Chris is an American dating columnist who is sharing his straight up wisdom on attracting, seducing and winning beautiful women. A bit of an alpha male himself check out his blog at

There are definitely varying degrees of shyness that men will exhibit with women. Some guys have no problems at all approaching and talking to women, and others are utterly terrified of even approaching a woman that they do not already know, or one that they do not know very well. And a lot of guys are really somewhere in the middle.

Sometimes they can confidently start a conversation with a woman, and then there are other times when they just cannot seem to make it happen.

I am going to kind of “target” this article at guys that are really uncomfortable when talking to women, and depending on where you find yourself, you may be able to pick up a few things here and there, even if you are more in the middle, so to speak.

First of all, I would like you to think of where the fear comes from. Was there EVER a time in your life that you did not have any fear about talking to women, or was it always that way?

I know for myself, that there have been times when it seemed like I could approach any woman that I wanted to and I did not even think twice about it, and there have been just as many times when I felt as though I could not even start a conversation with a butt ugly chick.

Obviously in those situations, where the woman is not attractive, it is not a situation where you are intimidated by her looks.

For many guys, the fear comes from the “unkown.”

What do I mean by this?

At many different points in your life, I can assume that the majority of your social circle, or your social network has consisted of mostly other men. Don’t count female family members, and I bet that the majority of the time, your social circle has mostly been other guys.

So, right there, you kind of have a disconnection from women, and you probably are not really sure what to talk about, and you have no real reference points in your mind that shows you that you can easily start a conversation with a woman.

Now, I can also bet that there have been times when your social circle did have at least a couple of females in there. Maybe it was in high school or college. During those times, I will also bet that you found it at least a little bit easier to talk to women.


Because you had those reference points in your mind, you have examples and memories of conversations with women, and that was enough to tell you that you DID know how to talk to women, at least on some level.

The reason why I am digging into this area, is because most men that have a REALLY hard time talking to women… don’t talk to women that often.

And that is the source of a lot of the fear and the awkwardness, it’s the inexperience.

So, here are 5 tips on how to overcome shyness with women and be able to confidently talk to women:

1. Become friends with at least one female.

And I do mean friends and nothing more. You want to introduce some females into your life and your social circle. The change that you can make just by doing this alone can be profound. One guy that I worked with took this one bit of advice and kind of ran with it. He wound up making friends with quite a few women, and suddenly he saw that he could talk to women, no problems at all.

He built new references and experiences in his mind, ones that he could pull from at any time, and realize that he DID have the skills to talk to any woman that he wanted. The result? He started dating more women in one year than he had in the previous 5 years.

2. Approach at least one woman per week that you do not know and start a conversation, no matter how small.

Eventually, if you really want to get this area of your life “mastered,” then I suggest that you up it to one woman per day. The point of doing this is not to get a date or a phone number, at least not at first. It’s about overcoming the “shock” of approaching women that you do not know, and starting a conversation with her.

Soon, whatever fears that you might have will start to subside, and you will realize that it can actually be kind of easy to start a conversation with a woman, even when you don’t know her at all.

3. Now that you have started to get female friends and started to talk to women that you do not know, start to build up for something more.

Once you have a female friend, and hopefully more than just one in your network, and you have started to approach women that you do not know and get a conversation going, it’s time to UP the ante. You now want to start at least getting some phone numbers from women.

When you approach a woman that you do not know and the conversation seems to be fun and maybe even a little flirty, ask her for her phone number. Sure, she might say NO, and she might just move on after that. The point is to get used to asking for her number so that way, the shock of doing that will just wear off.

4. After the first one or two or maybe even three women, you have probably gotten at least one phone number, and now, you want to get comfortable making plans or dates.

Obviously, you are not approaching women just to have a stash of phone numbers, right? The whole point in getting the phone number is to work up to a date with her, and of course, maybe even more than that. So, you want to get used to talking to her on the phone, at least enough to make plans.

Depending on your personality, a short conversation may be better and more effective than a longer one. The more silent pauses there are, the more it will seem like she would be bored on a date with you. So, if that is your personality, make it short, touch base with her, and get her to meet you somewhere. My favorite thing has always been to get a woman to hop on the train and head into Manhattan, yours may be different.

5. This is probably the MOST important tip of all– Think of EVERY FAILED ATTEMPT AS JUST A PRACTICE RUN.

If you think of every rejection or every conversation that leads to nowhere as just being a test run, a practice, then it will not have as big of an impact on you as if you think of it as being just another sign that you suck with women. You probably DON’T suck with women as much as you think you do, and when it starts to “click” and you start to get more and more dates with women, then you will look back on all of those failed attempts as just being either funny or a lesson learned and nothing more.

There is no shortage of women that are worth dating out there, so don’t have the mentality that you let one get away and that you might never get another opportunity like that. Look around, beautiful women are everywhere, and every day you can end up coming across a woman that is even better than the last.

Even though it can be intimidating at first, and you might think that you have nothing worth saying, the more times that you get out there, you will discover how to talk to women in a way that builds intense attraction.

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