I really used to suck when it came to talking to women. Like, I just couldn’t do it. Some time ago, I tried to talk to a rather cute girl who was waiting near a bus stop. It went something like this:

“Hi,” I said.

“Hi,” she replied.

“How are you?”

“Good,” she said. “How about you?”

“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.

I can tell you from experience that it sucks to be that guy who can’t talk to women and I don’t want that to happen to you. I used to be really awkward when it came to dating and I always blamed it on the fact that I was an introvert. Eventually, I had to accept that I needed to be better if I wanted to find love.

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

Before the Conversation

If you have the proper mindset before you even begin talking to her, it will make everything much easier. It’s a lot like how sports teams will actually warm up before an important game. For example, a basketball team might practice passing to each other and shooting the ball to help them get “in the zone” before the actual game. Similarly, if you get yourself “in the zone” before you approach her then it will make everything much, MUCH easier.

First, you want to be evaluating her just as much as she is evaluating you. This is still true even if you’ve never had a girlfriend before. If you’re desperate and you’ve been “lowering your standards” in order to try and attract ANY woman then you’re just setting yourself up for failure because most women find that unattractive. The cruel irony is that you might think you’re increasing your options by “lowering your standards,” but in reality, you’ve reduced them even further.

Secondly, you want to talk to her without expecting anything or needing it to go anywhere. Instead, you want to talk the mindset of: I’m just going to go up to her, introduce myself, and have a little fun. Maybe she’ll give me her number or agree to go out with me and if she does, great! But if she doesn’t, that’s okay too!  The important thing is to just have fun and enjoy being in the moment.

Here’s a trick that I like to use in order to make myself more confident before I try to approach women. I’ll walk up to a random stranger (man/woman/young/old, it doesn’t matter who), give them a genuine compliment, and then quickly walk away. Sounds simple, doesn’t it? It might even sound a bit weird or scary because…no one does that, right? Here’s the thing, though: You cannot possibly be shot down by the people that you approach.

Since you are not asking for anything, you risk no social rejection. And you will long be on your merry way before it can ever become awkward.

In addition, you probably made the day of everyone that you complimented. You’re now the mysterious stranger who stepped out of the shadows and brightened someone’s day before disappearing into the night. Like Batman! Seriously! Do this a few times and you’ll notice your nervousness around approaching women start to melt away.

Alright, Casanova, I know what you’re thinking. “What do I actually say to her?” Let’s get to the good stuff.

Step 1: Beginning the Conversation

The first thing you want to do is create a natural opportunity for a one-on-one conversation. Try to casually position yourself so that you end up next to the woman that you’re interested in. You can do this any number of ways and there’s no specific way that you need to do this. Here are a few examples you could try:

• [At a party or social gathering]

If she’s talking to a group of other people, wait for her to break off from the group or for the conversation to begin to die down before you start talking to her. Alternatively, you can introduce yourself to the group and join in the conversation before talking to her one-on-one. People generally enjoy meeting other people at parties, so don’t worry that she won’t be interested in talking to you.

• [At the gym]

Make eye contact with her and smile while she is exercising on one of the machines. Hop on some of the other machines and then “coincidentally” finish up with your workout just as she finishes with hers.

• [At the dog park]

Casually walk your dog so that it ends up next to her and her dog. Let your dog interact with hers before beginning the conversation. Women love men who have dogs! If you have a dog, use it to your advantage. A good conversation topic is the health benefits that dogs give their owners.

• [At the coffee shop]

If she’s just ordered her coffee and is waiting for it to be made, stand next to her while waiting for your coffee as well. Or, if she’s already sitting at a table then approach her from the side and stand next to her as you talk to her.

By doing this first, you’ll help make the conversation seem more smooth and natural. She’ll feel more comfortable because it doesn’t feel like you’re “on the prowl.”

Once you’ve casually positioned yourself next to her, you can open the conversation by talking about something contextual. For example:

• [At a party]

“How do you know [host’s name]?”

“I’m having a great time! How about you?”

• [At the gym]

“I see you working out here a lot. Are you an athlete?”

“I’m going to feel this in the morning”

• [At the dog park]

“Your dog is so cute! What’s his name?”

“Look at that! My dog seems to like you.”

• [At the coffee shop]

“What are you reading/studying/listening to?”

• [If she’s reading a textbook]

“I’m glad I don’t have to know any of that!”

Another way you can open the conversation is to simply introduce yourself and say “Hi, I’m Steve.” Or, you can give her a genuine compliment such as “I like your purse/shoes/jacket/hair.

It looks really cute!” Women spend a lot of time choosing their outfits and making sure that they look good before going out, so she will definitely appreciate a genuine compliment. If you’re feeling bold, you can even try saying “Hi, I thought you were really cute and I wanted to meet you.” This takes guts but she’ll probably be floored if you said this.

These are just a few examples of how to approach women. There are infinite ways you can begin the conversation with her. The most important part is to be authentic when talking to her. In other words, 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?

Step 2: During the Conversation

After you break the ice by talking about something contextual, the next step is to build rapport by making the conversation more personal. As Dale Carnegie wrote in 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. Try to find something that she would enjoy telling you about herself.

Depending on the context, you might be able to figure out what she is interested in. For example, if you’re meeting her at a dog park and she’s walking her own dog there then you can bet that she’s a dog lover.

Or, if you’re meeting her at an anime convention then she probably has a bunch of really nerdy interests. If she’s looking through a book at the coffee shop then she might enjoy reading fiction.

Also, you can try just asking her outright. For example, you could just say “What do you like to do in your free time?” And then whatever her answer is, talk to her about that. One of my favorite conversational techniques is to ask

“What is your favorite [movie/book/hobby/music/etc.]?”

and then follow up with

“What do you like about [her answer]?”

If she suddenly changes the topic during the conversation, it’s probably something that she’s interested in. Talk to her about that or ask her to tell you more!

How’s it going, champ? If she starts asking personal questions about you then she is probably interested in learning more about you. She might ask you some of the same questions you’ve been asking her.

“What’s your favorite [movie/book/hobby/music/etc.]?

What do you like to do for fun? Etc.”

Don’t just give one-word answers, but tell her more! Remember that if you’ve gotten this far then she’d like to know more about you.

For example, if she asks what your favorite hobby is then don’t just say “I like reading” but say something more such as “I’m a huge fan of reading.

I really liked The Catcher in the Rye because it’s so easy to relate to the main character when you were his age.” Just make sure you don’t dominate the conversation by talking about yourself too much. If she starts zoning out then you’re starting to become uninteresting. Ask her another question or change the subject.

Try to steer the conversation towards any common interests the two of you have. On a psychological level, we like people who are like us because it shows that we’re part of the same group.

As the conversation flows, listen to the things that she’s interested in or that she enjoys doing. If she tells you that she really likes watching Game of Thrones and you happen to be a huge fan as well, let her know and then talk to her about your favorite moments from the series.

And if you’re talking about one of your own interests and she happens to enjoy doing that as well, she’ll chime in and let you know. Talk to her about that some more! One of my friends is a huge bookworm and 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.

Step 3: Closing the Conversation

Okay, you’ve spent some time talking to her and getting to know her a little bit. At this point, do you still find her interesting? If not, that’s perfectly okay! Just politely end the conversation and walk away.

If you do find her interesting then you’ll want to get her phone number. Let her know that you’ve enjoyed talking to her and that you would like to see her again.  You can say something along the lines of “Hey [her name], It’s been cool talking with you. Let’s grab a coffee sometime” If she says yes, ask for her number. You can just say something simple like “Sweet, I’ll drop you a text” and then take out your phone.

Being Successful Talking to Women

What does it look like when you successfully implement these ideas? Let me show you.

A few years ago I was hanging out in the bookstore. As an avid reader, I enjoy reading novels and I had just finished the one I was reading so I decided to find a new book. After finding a new book, I leave the building and I see a rather cute girl sitting on one of the benches outside reading a book of her own. She looks interesting and I decide to go talk to her.

I approach the bench from the side and casually sit down next to her.

“Hey, what are you reading?” I ask her. This is a contextual question meant to break the ice. She’s already reading her own book and there’s a possibility that she might not be interested in making conversation, but I decide to go for it anyway.

She shows me her book. “Have you heard of it?” she responds. She’s asked me a question in return, which is a good sign that she would like to talk further.

“I’ve never heard of it. What’s it about?” I ask. She’s sitting outside the bookstore and she’s in the middle of a book. Based on this context, I think that she might be an avid reader as well.

“It’s a novel about magic and alchemy” she responds.

“Like Harry Potter?” I ask.

“Sort of. I love Harry Potter!” she replies. Bingo! I’m a huge fan of the Harry Potter series, and since she’s reading another novel about magic I figured that she’s probably a fan as well. We’ve discovered a common interest.

From here, the conversation flows much more freely for both of us. The two of us spend some time talking about our favorite moments from the series and we start to relax around each other. I tell her that I have to get going but I’d love to talk about our favorite books some more over coffee. She agrees and gives me her phone number.

Once upon a time, I would have been super awkward trying to talk to a girl I was interested in. This time, however, I didn’t need the conversation to go in any particular direction.

If she didn’t find me interesting then I would have just gone home and read my own book like I was originally planning to do. Before I talked to her, I told myself “I’m just going to go up to her, introduce myself, and have a little fun.” Now that I got her number, though, it looked like I was going to have a little less time to read my own novel.

That’s not a bad problem to have.

For more dating advice, feel free to check out Charming Introvert.

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