How to Be More Confident Around Women as an Introverted Man

IntrovertDear.com introvert confident around women

Let’s talk about confidence.

Growing up, it always felt like women liked the guys who were more confident and outgoing. Whenever I had a crush on someone, most of the time I would be too scared to ask her out. My mind would tell me things like, “She probably already has a boyfriend,” and if I did try to talk to her, I would become super awkward and would barely be able to say anything. The advice I heard over and over to be more confident was, “Fake it until you make it.” But that never helped me at all.

This makes it especially difficult because as men, we’re the ones who are expected to be the initiators when it comes to dating. It’s up to us to ask her out, go for the first kiss, ask her to be exclusive, and so on. And this can mean having to step way, way out of your comfort zone, especially as an introvert. So how are we supposed to be confident when it comes to dating?

Here are three things I learned about dating that helped me be more confident around women:

1. Don’t put her on a pedestal.

Several years ago, I had a crush on a woman I’ll call Joyce. She was stunningly gorgeous and I really liked her. She was always really friendly toward me. I began to imagine the two of us together. I fantasized about being in a relationship with her and having her as my girlfriend. If I saw her and was able to talk to her, it made my whole day. And if I went a few days without even seeing her, I became depressed — sometimes to the point of having trouble eating.

This went on for weeks, then months, and then over a year. They say there are “plenty of fish in the sea,” but I didn’t want to hear it. Did I ask Joyce out once during that entire time I obsessed over her? No. I knew that if I asked her out, there was a chance she would say no. And that would be impossible to deal with, especially after months and months of having become obsessed with her. It was easier for me to live in my fantasy world where the two of us were together then to face the reality that she may not actually want that.

Steven, you moron.

One day I learned Joyce was moving away and that I’d probably never see her again. That’s when I finally decided to ask her out. By that time, my expectations had become so high that there was no possible way she was going to live up to them. I had put her on a pedestal, and no woman wants that. She said no and, naturally, I was crestfallen. That night I shut myself up in my apartment and I cried myself to sleep.

Eventually I got over it, but that one rejection was a very tough pill to swallow. For months, I had pinned all my hopes on a single woman and that had made me desperate around her. Don’t do what I did. Don’t put her on a pedestal.

2. Give yourself permission to fail.

As introverts — and especially if you’re an INFJ personality type like me — we can be perfectionists. You may think you need to have the perfect opening line in order to begin the conversation. I always worried that I would stumble over my own words while trying to talk to her and that I would look like a complete fool. However, it turns out that this doesn’t matter as much as I thought it did.


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Being awkward can actually be endearing. One of the most attractive traits you can display when it comes to dating is authenticity, and someone who comes off as too rehearsed sounds inauthentic. Think about the guy in the bar who goes up to twenty women and uses the exact same opening line on each one he meets, immediately moving on to the next woman when it becomes clear that the one he’s talking to is not interested in him. He clearly only wants one thing, right? That’s a huge turn-off.

I used to worry that if I asked a woman out and she turned me down, she would later tell all her friends about it and they would laugh at me behind my back. As it turns out, the only person who is really going to spend a lot of time and energy thinking about our own failures is ourselves. Recently, I heard a story where a woman was walking to work and accidentally stepped in wet cement. The construction worker who was pouring the cement yelled at her angrily and she left feeling humiliated. The next day she went to the worker and apologized for having stepped in the cement. As it turned out, the construction worker didn’t remember her at all from the day before. He told her that it happens all the time and he couldn’t possibly remember everyone individually.

Everyone is that construction worker. Introverts, no one will ever judge you as harshly as you can judge yourself. Go out there and show her your best authentic self. Don’t worry about having to come off as Rico Suave, and give yourself permission to potentially get shot down or end up making a fool of yourself.

3. Don’t let your mind talk you out of it.

A lot of times, when I wanted to ask out a woman that I liked, my mind would give me a whole bunch of excuses to talk me out of it. I’d be scared and I’d invent all kinds of reasons not to talk to her, such as, “She would probably never be interested in me,” or “She probably already has a boyfriend.” And then I would hate myself later for not even trying. When these kinds of thoughts come up, what are we supposed to do about them?

According to Acceptance and Commitment Therapy (ACT), these types of thoughts are actually normal. Your mind actively looks for things that could go wrong because it’s better to be over-prepared than under-prepared. Our brains evolved this way. Before we started living in cities, this defense mechanism helped keep us from being eaten by tigers or bears.

What if these thoughts are true, though? Well, these types of thoughts can certainly feel like they are true, especially if you haven’t had a lot of dating experience. Everybody feels some anxiety when talking to someone they like or have a crush on, and it’s not a bad thing to feel that way. Obviously, if you know for certain that she already has a boyfriend, that’s one thing. However, if you want to talk to someone you’re interested in and your mind becomes overwhelmed with negative thoughts, try to remember that those thoughts are merely assumptions. And you know that old saying about making assumptions.

For more dating advice for introverts, check out my website CharmingIntrovert.com.

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Read this: The Introverted Man’s Guide to Talking to Women


  • chikashikaari

    Great advices! Although, not convincing.
    Never understood why men are supposed to ask women out.
    Isn’t that supposed to be a mutual interest?

  • Kat

    LOL, this applies to introverted women, too. I think I will stay single forever.. unless someone approaches me on their own 🙂