The Beginner’s Guide to Asking Women Out

As an introvert, I struggled a lot when it came to trying to date women. I hadn’t even gone on my first date with a woman until I was in my twenties, whereas some of my friends just seemed to naturally fall into their perfect relationships without even trying. It just seemed like for most guys, knowing how to approach women, talk to them, and get a girlfriend was just common sense. I used to believe that it was just something that men should be able to do.

Meanwhile, I didn’t know how to go about dating or even where to learn those skills. I had no idea what you’re supposed to say to a girl you’re interested in. Are you supposed to use a pickup line? Are you supposed to impress her? How do you start a conversation and what do you say to her? Sometimes I’d hear that you need to be very bold with women. Sometimes I’d hear that you need to be very direct. And sometimes, I’d read some PUA advice that made me question my faith in humanity. I just wanted to find a compatible woman to share fun times and love, to kiss and hold hands with and experience that sense of intimacy, y’know?

Now, things are different. I learned how to talk to women and get them to go out with me. I met this wonderful girl a while back and was able to successfully ask her out. Today, we enjoy a lot of fun times together and it’s amazing to experience that love we have for each other. And I was able to accomplish all of this naturally, without becoming a jerk or an “alpha” or resorting to any of those sleazy PUA tactics – me, the introverted late bloomer!

Honestly, if I can do it then you can too! Here’s my beginner’s guide for talking to women and landing dates:

Find a time to talk to her when she’s not busy

The first thing you want to do is find a time to talk to her when she’s not busy or preoccupied with something else. So, if you’re interested in that one barista at Starbucks then try to talk to her either when she’s getting off work or when there are no other customers. If you fancy that cute girl in your class then try to catch her when lecture is over (just please don’t try to do it during class! This should be obvious but I’ve seen someone try to do that before.) That beauty you see in the bar? As long as you’re not interrupting her conversation, go for it! You get the idea.

Once she’s available, approach her and…

Strike up a fun and authentic conversation

When I first started to try and date women, one of the biggest areas that I struggled with was that I had no idea what to say. It turns out that the answer might be simpler than you think. When talking to her, you should just aim to have a fun and authentic conversation with her. Don’t try to be flashy or impress her by being someone you’re not. Instead, let your natural personality shine through.

For example, in real life I’m kind of sarcastic, I speak softly, and I tend to use dry humor when talking to people. So, if I’m talking to a girl I’m interested in then I’m not going to try to talk to her in an overly-masculine and aggressive tone in order to try and impress her. That’s not who I really am inside. People can sense inauthenticity a mile away, y’know? As cliché as it sounds: just be yourself and try to have fun!

Starting the conversation can be as simple as saying “Hi, my name is Steve” or even just “Hi.” It really doesn’t matter too much how you begin the conversation. Just stay away from pickup lines, since most of them come off as inauthentic (unless you can pull it off in a really endearing way.)

To keep the conversation going, I suggest trying to find out something about her that she would love to tell you about. For example, maybe you notice that she has a folder with a photograph of a cute puppy on it. That might be a picture of her dog. Ask her about it! Displaying a sense of authentic curiosity and showing that you’re genuinely interested in learning more about her is a great way to build rapport.

Talk with her for a little bit and see how the two of you feel. If you’re having a really great time talking to her then go ahead and…

Ask her out!

Ask her to come with you to dinner, or to coffee, or some sort of event happening in your city…whatever! Just do it as confidently as you can and try not to come off as needy or desperate. Back when I was inexperienced, I used to be like “Umm…if you want…would you…maybe…like to get dinner with me…or something?” You can imagine how well that worked for me.

Instead, you can say something along the lines of “Hey, I’m interested in going ice skating at the park this Saturday. Why don’t you join me?” or “Hey, would you like to get a cup of coffee Sunday morning?” These types of questions are more non-needy. If you’re asking out someone that you just met or don’t know that well then you can try showing a little bit of vulnerability. You might say something along the lines of “Hey listen, I really enjoyed talking to you and I wouldn’t mind getting to know you better. Would you like to get a cup of coffee this Saturday?”

Make sure you have a concrete time and place in mind when asking her the question. She’ll be looking for you to lead so don’t make her to plan it for you. Instead of saying “Would you like to get dinner sometime?” ask her “Would you like to get dinner at Mater’s this Saturday?” Remember that if she agrees to going out with you “sometime” then she hasn’t actually agreed to doing anything at all!

Okay, that’s enough with the examples. You get the idea. Go and ask her out already!

She said no (or “maybe” or some variation of “I’m busy”)

Bummer, man. It sucks to hear that. No, you’re not a loser for trying. And no, she’s not going to think less of you or laugh about it to her friends. We all get rejected sometimes.

Keep in mind that it’s not always your fault. Maybe she prefers a different type of guy, maybe she already has a boyfriend, or maybe she’s just not interested in dating anyone at the moment. Who knows? Typically women will try to let you down easy instead of flat-out saying “no.” Instead you can expect to hear something along the lines of “maybe” or “I’m busy” or “I can’t make it.” Often, if a woman is busy but she is still interested in going out with you then she’ll instead suggest alternate times for you to go out. So, don’t pout or keep trying to suggest different dates if she says that she’s busy. Instead, behave like you are okay with it. You can say something along the lines of “Sure, no problem.”

You took a chance and stepped way outside of your comfort zone there. So, congratulations! Go ahead and treat yourself. Grab some Doritos, play some Fallout 4, watch some Game of Thrones, or whatever else you like. You deserve it.

She said yes!

Congratulations!! I know you’re excited, but try and resist the urge to start dancing.

Get her phone number if you don’t already have it so that you have a way to keep in contact with her. She won’t say no to this if she’s already agreed to going out with you, so just say “Can I get your phone number?” Make sure to work out the logistics of the date with her before the actual event so there’s no confusion: Are you meeting her there or picking her up? What time are you two going out? Where are the two of you going? Etc. etc. You can do this while talking to her now or over the phone later.

Okay, now you can start dancing!

What next?

If you’ve enjoyed this guide and you want to see more, I’ll be creating more dating guides such as this one about topics like: what to do after you land that first date, how to go from dating someone into being in a relationship, and how to be confident when talking to women. Sign up for my newsletter below and you’ll receive these articles in your inbox as they are written.

Good luck and happy dating! Ciao!

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