Three ways I made myself more confident around women

Let’s talk about confidence.

When I first started looking for love, I always wished that I could be more confident around women. If only I were more confident, I could go right up to a woman that I was interested in and just start talking to her. No more feeling awkward or nervous. No second guessing myself.

However, I’d usually just find some way of talking myself out of it. I’d tell myself things such as, “She probably already has a boyfriend” or “Someone like her would never be interested in me”. If I had a crush on someone, I would try to psyche myself into asking her out beforehand but when the time came and I did see her I just told myself, “She’s probably busy. I’ll ask her out tomorrow.” Of course, when tomorrow came I would just tell myself the exact same thing.

How do you become more confident around women? Especially if you haven’t had a lot of success before?

One of the very best descriptions of confidence that I’ve ever seen comes from the book Mate by Tucker Max. He writes, “Confidence is the realistic expectation you have of being successful at something, given (a) your competence at it and (b) the risk involved in doing it.”

There are two important parts to that definition. Your confidence reflects how likely you realistically believe that you’re able to succeed at something, given:

  • Your level of competence at it
  • The risk involved in doing it

When you positively influence these two factors, it naturally makes you more confident. Here are three specific things I did that made myself more confident around women.

I learned to stop putting women on a pedestal

A long time ago, I had a crush on an acquaintance named Joyce. It started off as a small crush, but over time I started thinking about her more and more. I began to imagine the two of us together and I fantasized about us being in a relationship. Eventually, I started to become obsessed with her to the point where I’d overanalyze every single interaction we had with each other. She smiled at me today…does that mean she’s interested in me?

If I didn’t see her for a few days, I would start to have trouble eating or sleeping. This went on for weeks, and then months, and then over a year. My friends told me that I was becoming too obsessed and that there are “plenty of fish in the sea” but I just didn’t want to hear it.

I never asked her out at all during that time. At first I was too nervous. But over time, I had built up a mental image of her that would be impossible for any person to fulfill. I had put her on a pedestal. At that point, if I asked her out and she turned me down then the illusion that I had built for myself would come falling down. It was easier to continue living in my fantasy world than it was to ask her out and risk being rejected.

Some time later, I learned she was moving away and that I’d probably never see her again. That’s when I finally decided to ask her out. She turned me down. In an instant, my fantasy world had shattered. That night I shut myself up in my room and cried myself to sleep.

*sigh* Steve, you were such a moron back then.

It sucked at the time. A lot. But looking back I’m actually glad she turned me down. After all the time and energy that I spent fantasizing, I don’t think I ever loved the real Joyce. Just the Joyce I had built up in my head. She was a completely different person.

One of my biggest problems with women is that I’d become overly invested in her even before I talked to her or asked her out. In terms of Tucker Max’s definition of confidence, this influenced the risk involved in talking to women. By putting her on a pedestal even before I got to know her, I risked emotional devastation if she turned me down.

What I learned to do is to not have any specific outcome in mind when I interacted with women. I stopped requiring myself to get dates or phone numbers with the women that I talked to. Instead, I would go up to women and just be genuinely curious about her. That’s it. If it led to something, then great! And if it turned out that we’re not compatible, that’s okay too! Doing this helped take the pressure off of interacting with women and it helped me feel a lot more relaxed.

I learned to plan out what I was going to say to her

A while ago, I happened to run into a cute woman and we ended up hitting it off. She gave me her phone number and told me to call her. However, later when I actually did try to call her I ended up having a hard time finding the courage to do so. I would type her number into my phone and then immediately delete it. Then I would type her number again and then let my finger hover over the ‘Call’ button before deleting her number again.

I kept trying to psyche myself up into calling her. I told myself, “This time I’ll call her! Okay, this time I’ll actually call her! For real, this time!” I kept going back and forth like this for over an hour before I eventually just told myself, “Forget it. I’ll call her another time.”

As it turns out, the biggest reason I was so scared to call her up is because I had no idea what to say to her at all. What would I even say to her? Should I ask her how she’s doing? What would we talk about? Should I ask her out? To where?

In terms of Tucker Max’s definition of confidence, my level of competence was low because I had no idea what to say to her. Calling her without even knowing what I was going to say would have been a recipe for disaster. My unconscious mind realized this and tried to warn me by making me too nervous to go through with it.

That’s why no amount of psyching myself up was going to make me more confident. No matter what I told myself or how much I tried to “man up” or “fake it until I made it”, it didn’t change the fact that I had no idea what to say to her.

So, I rehearsed it. I mentally prepared a list of interesting things that I did in the last few days and I came up with a few questions I could ask her in order to make small talk. I researched come interesting places nearby to take a woman on a date and picked one that I thought was interesting. Finally, I practiced asking her out several times until I could do it without sounding totally nervous.

It’s impractical to plan an entire conversation, but it helps if you have at a least a rough idea of what to say to her. Do you have an awesome job? An adventurous story? Read something unusual recently? It really helps if you have a few things prepared beforehand to talk to her about.

I looked down at my cell phone. Taking a deep breath, I dialed her number and pressed the ‘Call’ button.

I stopped letting my doubts control me

Whenever I wanted to talk to a woman I was interested in, my mind would never fail to come with several reasons as to why I probably shouldn’t do it. It would tell me things such as “She probably wouldn’t be interested in me” or “She probably already has a boyfriend”. I used to believe that having thoughts like these made me unconfident and I hoped someday would come when I wouldn’t have these types of thoughts anymore.

That time never came. As it turns out, being be confident does not involve talking yourself out of these types of thoughts. It involves having these thoughts and doing it anyway.

If you think that she probably won’t be interested in you or that she probably already has a boyfriend then I’m not going to try and convince you otherwise. Trying to force these types of thoughts away is like trying to stop yourself from thinking of a pink elephant. The more you try to push them out of your head, the harder they push back.

Instead, the way to overcome these thoughts is to go straight through them! Think that she wouldn’t be interested in you? Talk to her anyway! Think that she probably already has a boyfriend? If you don’t know 100% that she has a boyfriend, then maybe you should go for it anyway!

Yeah, it’s scary. You’re putting yourself out there and risking getting rejected by someone you’re romantically interested in. That’s never easy. Everyone feels nervous around talking to a woman that they’re interested in.

But you know what? I’ve seen men become more confident even after they’ve just been turned down by a woman. It takes a huge amount of courage to go up to a woman, talk to her, and then ask her out. It’s much easier not to. By actually taking that step and doing it, you scale a massive personal mountain. And by asking a woman out once, you prove to yourself that they you’re capable of doing it a second time. And a third time.

And from there, it’s only a matter of time until you do find someone that you connect with.

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