Woman Smiling on Rock - Starting a Conversation with a Beautiful Woman

Starting a conversation with a beautiful woman can be difficult.

Today, we’re going to make it easier.

Until you understand certain things, the whole process can be nerve-wracking. Since many guys worry that if they can’t even start a conversation, how can they be comfortable flirting, escalating, and getting her number?

The reason starting a conversation with a beautiful woman is so hard for a man is that he puts her on a pedestal. He may think of her as almost non-human: a surreal, impenetrable, unaffected fairy-queen. Not quite, but almost!

Here’s the truth:
She is a human, and you are a human.
Together you are exploring a potential connection, big or small.

How do you work with this? How do you make starting a conversation with a beautiful woman easier on yourself?

You’re about to find out. Here are three ways to make starting these conversations easier on yourself, no matter how attractive she is:

1. Know what to say in a given situation.

The best way to start a conversation is to point out something you notice. It has to be sincere and top-of mind for you.

Anything about her or about the environment you’re in is fair game.

Whatever you notice that helps you with starting a conversation with a beautiful woman will fit somewhere within these three categories:

  • You
  • Her
  • The Environment

Here are a few convo starters that you’ll find more of inside this guide on conversation topics and tips, and this one on how to approach a woman:

The venue at hand:

This fits into the “Environment” category. Whether you’re at a yoga studio, a class, or a show, have you been to this place before, and if so, have you seen her?

Depending on whether or not you have been or have seen her there before, you can start a conversation accordingly:

  • “Oh I’ve been coming here regularly, but I don’t believe I’ve seen you before. Is this your first time?”
  • “This is my first time here. Have you been here before?”
  • “I’ve noticed you around, but I don’t believe we’ve met. I’m X.”

An observation about the environment:

This also fits into the “Environment” category. It’s an easy way to start a conversation about something you notice and like.

Environment-based topics include…

  • The weather that day/evening
  • Her/your drink or food
  • The host/hostess

A genuine compliment about her:

Whatever you tell her must have naturally occurred to you in your thoughts; it must be genuine and true. Otherwise, talk about the environment instead!

If you notice something you like about her, by all means tell her if you are inspired.

Although if you would feel more comfortable talking about the environment, just stick with that for now while you get more comfortable talking with women.

Starting a conversation with a beautiful woman based on what you notice about her can include…

  • Her dress or shoes or jacket
  • Her hair
  • The way she has about her; her vibe

Obviously, never say something that isn’t sincere. Especially if she’s a quality woman, she can see right through that.

Plus, it’s not fun to be less than genuine. Be honest.

So, all those are great helps to starting a conversation with a beautiful woman. 

For even more on this topic, there is our 6,300-word guide on how to carry the conversation from there, and here is our piece on how to best approach a woman as an introverted man.

Now you have a great head start in knowing what to say and saying the right things for you, her, and the situation.

Next: how do you shake the feeling that she’s on some sort of pedestal? As long as you’re keeping a strong sense of self, you will be safe from that.

This bring us to our next point:

2. Maintain a strong sense of confidence.

While starting a conversation with a beautiful woman, it’s important to maintain a strong sense of yourself.

For you to feel good to her, you must hold your own ground with your own natural confidence instead of “flopping onto her space” in a needy way with your energy / vibe.

For 22 pages of detail on how to do that, check out my free ebook on finding your personal vibe and why pick-up doesn’t work for introverts and what works instead.

Inside, there’s an exercise to find your Attractive Values (the values you hold dearest as your life-compass) and your Attractive Factors (the qualities you get complimented on most).

Once you’ve done those exercises…

  • Go through each Attractive Value and ask yourself, “What does this value mean to me?”
  • Then go through each Attractive Factor, and ask yourself, “What do I most enjoy about having this factor?”

It helps to write this down as you go.

The result is you feeling more of yourself, knowing what you bring to the table and why it’s awesome. 

When your unique value and vibe is top-of-mind for you, it becomes top-of-mind for the woman talking with you.

She can more easily see the man you are.


If you feel good, others feel good around you too. 

3. Know when and how to touch her.

There are 3 stages of touch that I teach our clients:

  1. Friendly Touch
  2. Flirtatious Touch
  3. Making The First Kiss Inevitable.

When you’re just meeting and starting a conversation with a beautiful woman, you can focus on that first stage: Friendly Touch.

Touching her in a friendly, no-pressure way makes her at ease around you. 

Reason being, it shows that you feel comfortable in your own skin around sexual attraction.

Yay! Who doesn’t find that sexy?!

Here’s how to touch her:

When starting a conversation with a beautiful woman, you can lean in and touch her on the hand, arm, or knee if you’re sitting. If you’re standing, lean into her lightly with your shoulder or arm for a second or two, then pull away.

It feels natural when there’s already a great rapport there.

Pro Tip: You can practice this purely friendly touch in a zero-pressure way with attractive women who are already in a relationship, because there’s no expectation on you. You are not going to do anything. You’re not even flirting! You are just practicing this basic friendly touch you could do with anyone.

One of our clients did this, and then when he met a beautiful and available woman on the plane, he wooed her instantly. She was touching him for the rest of the plane ride and eagerly entered her number into his phone. It was so easy to touch her because he’d had all that zero-pressure practice with his attractive, already-attached friends!

Woman's Feet Crossed - Starting a Conversation with a Beautiful WomanTakeaway:

In summary, there are three components to starting a conversation with a beautiful woman in the best way possible:

  1. Knowing what to say in that particular situation.
  2. Keeping your sense of self, a basic sense of confidence.
  3. Integrating touch in the right ways at the right times.

At the end of the day, starting a conversation with a beautiful woman is not all that daunting when you know what to do!

Here are a few follow-up resources for you:

If you are wanting hands-on dedicated 1:1 support with your dating life, learn more about our program. If it resonates with you, apply to speak with us about it today.

Editor’s Note: I originally published this post in August 2015, and in September 2017 I updated it for clarity and helpfulness.