Seduce Like Casanova: Ask ‘Why?’

There she is right in front of you, and she looks stunning. Time seemed to stand still for a second the moment you laid eyes on her, and she smiled at you when she saw you.

Perhaps you’re on a first date with her, or maybe you just saw her across the way and felt your heart start running a mile a minute. Or maybe even came across her profile online (in which case you’ll need to know how to get her on a date with you, get the free report here).

Either way, you need to talk to her. This here could be your future wife, future baby mama or even something else entirely!

But there’s a problem… what the hell do you talk about with women?

That’s what we’re going to dive into today, let’s get started.

Where are you from?

Chicago, you?

Oh cool, I’m from Nashville


Yea… so whattya like to do?

and etc.

Oh my god… I want to slit my wrists right now…

Have you ever had a conversation like that?

It’s okay to say yes, I won’t judge you because I’ve had a SHIT TON of conversations exactly like that.

Can you feel how awkward that conversation is just by reading it?

It’s awful… and that’s how most people’s conversations are. They’re just a half-step away from being a job interview…

But what should we do instead?

What to Talk to Women About?

Some of the best things to talk about with women all involve asking ‘why’. Though you don’t want to actually say ‘why’ like an annoying 3rd grader.

But you do want to have that in the back of your mind when talking to women (and this helps a lot with people in general, not just women you think are drop dead gorgeous).

Why? In Practice

Let’s see the above conversation in action again when our inner annoying 3rd grader takes over.

Let’s assume you’re not in her home town, which is Chicago for this example (I’ll show you a similar conversation if you’re in her hometown in a second):

Where are you from?

Chicago, you?

Nashville, what made you want to move here?

School *quick note: this is a boring answer, so we want to get off of this subject and onto something else. However, this answer is very important because it allows you to easily come back to it later*

I see. Tell me, in this whole big world where you can go anywhere, where’s the one place you would go if you could go there for your school instead?

From there you can take the conversation anywhere you need it to go. You can also come back to the school answer to do this exact same thing all over again.

But let’s talk about what happened up there. First off, school is a boring subject, and quite frankly, so is asking a girl where she’s from.

It’s small talk, and it’s an important and necessary evil. What small talk allows us to do is to dig into what makes a girl tick. It allows us to ask about things that are far more important to her, like her hopes and her dreams and other motivations.

In the above example, once she tells you where she would like to travel to you can follow up with asking her what about it draws her to that place in particular. This gets into her motivations as a person and getting her talking about why she does what she does.

It also makes her emotionally invest in talking to you and brings up good emotions.

Say for instance that she launches into a story from her childhood about how she traveled to blank before and did all of this amazing stuff. She’s going to remember those emotions and she’s going to begin to associate those emotions to you.

It’s beyond the scope of this article, but it’s called anchoring. Here’s an article about it if you want to learn more about it. 

This can also work even if you’re in her hometown, let’s look at the above example again:

Where are you from?

Chicago, you?

Nashville, what made you want to stay here?

My family lives here

And from there you can go back into talking about traveling and her experiences. You can also ask about her family later on.

Note: if she gives you an enthusiastic answer you can do this same thing with why she wanted to stick around or moved to a place in particular. In the examples I’m assuming that she’s not excitedly talking about the answers she gave you.

But if she does give you an excited response you can simply ask her about it:

Wow you seem kind of excited, what makes you so excited about it?

Now, she might just be excited about the subject or she might be excited about you. Both are great! If she’s excited about the subject she’ll launch into a story about it.

If, however, she’s excited about you she’ll simply say something like “I don’t know” or something similar. If you get a response like that then you have a big hint that she probably likes you and you can continue the above conversations the exact same way.

Those were just examples about where she lives to get into travel and different experiences, but there are other things you can talk about as well.


The best things that you can talk about with women are their hopes and dreams, experiences they’ve had, their childhood memories or even just who they are as a person (which means their motivations for doing what they do).

In addition, you don’t want to forget to use statements and relate back to what you’re talking about otherwise it’ll start to feel like an interview. I go over this a little bit more in this article. 

Just remember, start with boring whatever questions and then follow up and dig deeper:

  1. Where do you work?
    1. Blablablabla
      1. Do you enjoy it?
      2. If yes, ask what their favorite part about it is. What about their least favorite part?
      3. If no, ask them what they would do and where they would do it if they got paid exactly the same thing they do now
  2. Where are you from?
    1. Oh is it true what they say about people there?
      1. That they’re huge dorks lol (make sure they understand that you’re teasing!)
  3. Tell me what 10 year old you was like. What were some of your hopes and dreams?
    1. What made you change and do what you’re doing now?
    2. Or, that’s so awesome that you stuck with it! I bet you face a lot of challenges to get there
  4. When did you have your first kiss/lose your virginity?
    1. Always a guaranteed story there. Just follow-up with stuff like “I bet it was awful” or even “I bet you were both nervous as hell”
    2. Quick note: this isn’t something you’ll bust out in the first 2 minutes of conversation, just keep this one in your back pocket if you need it later. 

The main thing about questions is to get the other person talking, then dig deep into the why of their answers. You can always go further into a subject by asking why (but do what I did above and draw it out a little bit, always asking someone why is incredibly annoying so mix in statements).

When you dig deeper into a subject always try to find out what their motivations/thoughts/emotions were as they were going through it. This alone can help create a bond with the other person.

Ask Why, But Don’t Forget to Tease

Something else you’ll want to get into the habit of doing is mixing in teasing comments every once in a while (like the everybody from blank is a huge dork example above). Otherwise you’ll just be a one-trick pony at best, and at worst you’ll land in the friend zone. .

Here’s an example I had with a cashier today:

I don’t need a bag

*looking at the bag guy* He’s easy

*in a fun tone and obviously not serious* Hey now! I have standards ya’know! That hurts my feelz

Clearly she meant that I was making their jobs easier, but I turned it around and ‘accidentally‘ misinterpreted it to mean that I’m a whore.

She got a big smile on her face as her jaw dropped *did this sexy guy really just say that?*

Meanwhile the bag guy loved it and started to play along:

Hey you don’t have to put his business out there like that.

He obviously knew I was joking and was just playing along. She knew I was joking and it was just a fun time. The interaction only lasted maybe 5 seconds but I probably made their day. And all I did was make a single teasing comment.

Also a quick note: I’ve talked to this girl before. We’re not exactly bff’s but we’re not strangers, she recognizes me. If we were complete strangers this would be more difficult to pull off. Not impossible, but not something I’d recommend. You want to be at least a little comfortable with each other before making sexual comments like that. Though with the dork example you can do that right away because it’s so harmless. 

Little stuff like that. With teasing, you’re not trying to be an asshole, you’re just making little playful comments about things that don’t really matter in the long run.

Teasing her about calling me a whore is okay. Telling her that her outfit sucks is too far into the asshole zone, not going to work out with healthy women.


I go into this a little bit more in the above article, which is linked here again for easy access.

But to take it to the next level you will want to relate to what she’s telling you with stories/statements/memories of your own. This way it’s an exchange of information instead of her just telling you her whole life story and you standing there like a rock. As always, you need balance when you do things.

So try not to get too caught up in asking questions, teasing or even relating.  This is something even I have to remind myself of sometimes as I love to hear about everyone’s stories.

The real thing you want to do is to find out why she does the things that she does and then relate your own experiences with hers. This makes you seem similar to each other (without coming off as a yes-man).

People like people that like them/understand them. And it’s a neat little mental shortcut if you can show the other person that you have similar worldviews/experiences because then they will feel like you understand them on a deeper level than almost anyone else ever will.

That’s it for a few things to talk about with women today! In future articles I’ll dive more into conversations with women, including teasing and even relating to women.

Keep Moving Forward

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