An Introvert’s Guide to Talking to Women

Note: A version of this article was originally published on Introvert, Dear

A few years ago, I happened to run into a woman that I used to have a massive crush on. I’m fairly certain that she used to like me, but nothing ever came of it and eventually we lost touch with each other. So, my heart skipped a beat when I saw her at the bus stop.

“Molly?” I asked.

“Oh my God, Steven!” She ran over and gave me a huge hug. “How have you been?”

“I’m good. How are you?”

“Good, good.”



(Uh-oh, awkward silence! How do I keep the conversation going? What do I say next? Do I make a joke? Should I comment on how she looks? Think, Steve, think!!)

“So, the weather’s pretty nice,” I muttered.

“Yeah,” she replied.

(The weather? Really Steve??)

“Umm, my bus is here. I need to go,” she finally said.

She stepped onto the bus and my heart sank as I watched it grow smaller in the distance. I was just about ready to bang my head on the concrete until I passed out.

When it came to dating, I had been awkward for a long time and I always blamed it on the fact that I’m an introvert and INFJ personality type. Eventually, I realized that if I wanted a girlfriend, I needed to get better at talking to women. What got me here wasn’t going to get me there.

Successfully talking to women doesn’t have to be reserved for those rare people who are born confident or are extroverted. I’ll show you how to talk and what to say so you don’t have to feel awkward again.

Be Your Best Authentic Self

Okay, raise your hand if any of this describes you:

  • People ask you “why are you so quiet?” like, 10 quadbillion times
  • You tend to want to leave the party early (or hide in the bathroom) and no one else understands why
  • You carefully think through what you’re going to say or do before you do it
  • You feel tired or want to take a nap after socializing with others for too long.

If this describes you, then you are probably an introvert (like me). On the other hand, if you’re the type of person who actually…enjoys…making small talk with strangers *GASP* then you might be an extrovert. If so, you probably don’t need to spend your time reading this. Instead, here’s a picture of my dog wearing sunglasses.


Never seen something like that before, am I right??

As introverts, we face a lot of pressure to be more like extroverts. Susan Cain, the author of Quiet: The Power of Introverts in a World That Can’t Stop Talking, calls this the “extrovert ideal.” For a long time, I always thought that something was wrong with me because of my introverted qualities and that women would never find me attractive.

After all, one of my friends who I always saw getting dates had the opposite personality as I did. He loves to surround himself with people all the time. When he talks to women, he is very aggressive and makes the conversation overtly sexual very quickly.

That’s not me at all. I’m introverted, reserved, and gentle. After watching my friend succeed seemingly all the time while talking to women, I started to become afraid that I would have to change my personality to be more like his if I ever wanted to get a girlfriend.

I tried to behave more like my friend. However, I didn’t achieve any success even though I was basically doing the same things he was. I also started to feel like I was being an actor by going against my own personality.

What was I doing wrong?

As it turns out, women could sense that I was being inauthentic—and they were turned off by it. 

I found myself succeeding when I behaved authentically. When talking to women, you should be your best authentic self. Or, you should be the version of yourself that your friends and loved ones enjoy being around. How do you behave around the people you are comfortable with and what is it that they like about you? As an introvert, you have your own strengths that are uniquely yours. You are more creative, a better listener, and more perceptive than many extroverts. Play to your strengths!

Talk to Her About What She’s Interested In

A while ago, I was at a weekly gaming meetup held close to where I lived and I met this cute, quiet girl wearing a pair of glasses. After I introduced myself to her (“Hi, I’m Steven”), she told me her name (“I’m Molly”–yes, this is the same “Molly” I mentioned in the beginning of this article). She started by admitting that she was somewhat of a quiet person and that she hoped I didn’t mind.

“Oh, good,” I thought to myself, “because I sort of am too.”

To my surprise, we ended up talking for almost an hour! She told me all about how excited she was to see the new Pirates of the Caribbean movie when it was in theaters and how she was anxiously waiting for the next Harry Potter book to come out. She explained how she was trying to create her own computer game.

All of that from a self-proclaimed quiet girl.

As Dale Carnegie wrote in his book How to Win Friends & Influence People, becoming a good conversationalist involves talking in terms of the other person’s interests and listening to them when they talk about themselves. This shows you’re interested in her values, attitudes, experiences, and beliefs. You’re interested in who she is as a person.

So, try to find something that she would enjoy telling you about herself. A great way to do this is by asking open-ended or “why?” questions. When she tells you something about herself, listen to what she has to say. Then, ask some follow-up questions based on what she just told you or relate it to yourself.

Talk About the Things That Make You Interesting

If she is interested in you, then she would probably like to learn more about you too. Just like how we looked for things that she would love to tell you about herself, she will be looking to talk to you about the things that get you excited.

Does she ask you open-ended questions about yourself? This basically means, “I want to learn more about you.” Tell her about some of the things that make you an interesting person. Do you have an awesome job? An adventurous story? Read something unusual recently? Tell her about it!

Try to find something that the two of you are passionate about or have in common. One of my friends is a huge bookworm. When he met his girlfriend for the first time, he discovered that she also really enjoyed reading. They spent a long time talking about the stories they read and trying to convince the other person to read their favorite book.

However, just make sure that she is actually interested in what you’re telling her about yourself. Don’t get carried away and make the conversation entirely about yourself. If she is zoning out, change the subject or let her get a word in.

Being Successful Talking to Women

Looking back, there are many ways I could have handled it better when I ran into Molly at the bus stop. I could have asked her where she was taking the bus to. I could have asked her if she ever finished that game she was trying to make, or if she ever got around to reading the latest Harry Potter.

Better yet, I should have asked her out the first time I met her.

Recently, I saw her Facebook profile and she’s in a relationship with a great guy. Well, I don’t actually know the guy, but I want to believe that he’s a good guy and I want to believe that wherever she is right now, she’s happy.

I don’t want this to happen to you, though. No matter how introverted you are or how awkward you might feel around women, I want you to know that it is always possible to improve yourself. Don’t be the guy who misses out because he doesn’t know how to talk to her. I can tell you from experience that it sucks to be that guy.

To make this as easy as possible for you, I’ve put together a “How to Talk to Women” cheat sheet. Just enter your email below and I’ll send it right over to you.

Update 1/31/19: The “How to Talk to Women” cheat sheet is now an EPIC 12-page guide covering everything from beginning the conversation, keeping it going, making it interesting, and flirting. It also includes the original cheat sheet. Enter your info and I’ll send it right over to your inbox!

10 thoughts on “An Introvert’s Guide to Talking to Women

  1. WOW! Thank you so much. Your insight was so spot on I couldn’t believe it! It’s as if you took the words off my mouth when it comes to painfully awkward interactions. It’s a very succinctly written article and I’d love to hear some more of your tips.

  2. Wow! Am sorry you and Molly didn’t end up together. Okay there is this girl am totally into, we both love the same things eg. Movies and anime. Before I visit her, I’ll think about the movies I want us to talk about . It has been going like this for days that I never talk about my feelings because I feel it’s weird for me to talk about them. Okay now we have finally graduated from school and we are about to travel to our various homes, I was sad that I won’t see her again that I started feeling lonely that I’ll be crying at night in my room. Her friends knew that I had feelings for her because I could talk to them about it and how much I’ll be sad when she leaves. Then the day before she traveled, I finally wrote a letter to her which says how I felt. The next morning, before she left she dropped a letter under my door and said she can’t wait and she is leaving now because then I was in the bathroom. When I came out, I read the letter and it said “I which you told me this a long time ago at least our last days will be memorable and romantic”. She was already long gone am already missing her and I haven’t even said goodbye. I left my room and ran towards the bus stop till I reached her. My eyes were already red and she said to me “no guy has ever cried for her” we talked a little and we switched contacts. As boarded the bus and it was leaving, I think I saw her cleaning tears from her eyes. Then some mins later she sent me a message say “I love you… it’s now I know, I really love you…” I replied back to her. But now that she is gone, I don’t really know what I’ll be saying over the phone and since she is my first girlfriend, I don’t just know what to do.

  3. After I initially commented I seem to have clicked on the -Notify me when new comments are
    added- checkbox and from now on whenever a comment is added I recieve
    four emails with the same comment. Perhaps there is a way you are able to remove me from that service?
    Appreciate it!

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