How to Start a Conversation with a Woman: 3 Steps

Starting a conversation with a beautiful woman can be difficult.

This is especially the case when you’ve gotten questionable advice, like…

  • “Talk about your favorite TV shows!” 
  • “Use a pick-up line on her!” 
  • “Just say something random!” 

Oh my goodness.

If you’re as creeped out about those prospects as I am, let’s move WAY past them. We don’t need them!

Today, we’re going to make it easier with some solid conversation starters for you.

Before we get into it, cut yourself some slack because the whole process can be quite nerve-wracking, even without the above bad advice weighing you down.

A lot of guys worry about how to make eye contact and look for a good sign she wants to be approached.

And then once they figure that out, they worry about how to make a good first impression, how to start a good conversation, and how to keep things rolling towards a first date.

It’s all quite a lot!

Refreshingly, you don’t need pick-up lines. You don’t need to show off.

You don’t even need 100% perfect body language or conversation skills to start improving in this area.

The first thing you can do to make this all a lot easier and less stressful is this:

Don’t put a woman on a pedestal.

She doesn’t even like it up there, because it creates so much distance between the two of you.

It’s not sexy to her if you think of her as almost non-human: a surreal, impenetrable, unaffected fairy-queen.

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

How do you work with this?

How do you open up the way for a genuinely great first conversation?

You’re about to find out.

Here are three steps to starting a conversation, no matter how attractive she is:

1. Know what to say in a given situation.

Awesomely, this requires zero memorization. You don’t have to have cheesy lines in your back pocket (as all that cheese would get messy anyway).

Rather, keep things simple, like this:

The best way to start a conversation is to point out something you notice in the environment around you. 

This way, it’s sincere and top-of-mind for you.

Anything about her or about the environment you’re in is fair game to lead into a casual conversation that feels relevant and natural for both of you.

Conversation starters fit within these three categories:

  • You
  • Her
  • The Environment

These are great alternatives to a one-word “hey!” because if you say that, great, but what do you say next?

Exactly.

No idea.

Not to worry!

With the conversation starters that I’m about to share with you, you’ll be automatically set up to take the conversation further.

(Note: For further reading on this topic, check out 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 or any type of regular meet up or event, and you see an attractive woman, you can ask yourself, “Have I been here before, and if so, have I seen her?”

Depending on your answer, you can start a conversation accordingly:

  • You’ve been but haven’t seen her: “I’ve been coming here regularly, but I don’t believe I’ve seen you before. Is this your first time?”
  • You have not been: “This is my first time here. Have you been here before?”
  • You have been and have seen her: “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.

This sets a positive tone, which is infinitely sexier than a negative tone, and it lifts the mood for both of you in a natural way that you don’t have to force or fake. It’s a win-win by you noticing something you like about what’s around you.

Environment-based conversation starters include…

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

A genuine compliment about her:

Complimenting her can be a really natural thing to do because, after all, there was something you like; otherwise you’d not have approached her.

That said, stay away from direct physical attributes, and instead compliment her on something that she put effort into, something that shows her style or her values (her beautiful dress, something kind you just witnessed her do, etc).

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

If you do choose to start a conversation based on what you noticed about her, you can mention…

  • Her dress, shoes, jacket
  • Her hair
  • The way she has about her; her vibe
  • Something you witnessed her do or say that you liked

See how natural that would feel?

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

So how do you make sure your small talk increases the possibility of attraction, instead of leading straight to the friend zone?

This leads us to our next step:

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 a sense of natural confidence instead of “flopping onto her space” in a needy way with your energy or vibe.

For 22 pages of detail on exactly 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 that ebook, 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.

When you’re bringing your A-game through your confidence, then you naturally ask questions in a natural way and share in a confident way. Conversation flows when you feel good.

Remember:

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

3. Know when and how to touch her.

Touch/proximity is *so* important.

In fact, it’s just as important as words are, if not more so, when it comes to attraction.

Whenever you’re connecting with a woman, remember there are TWO conversations going on at the same time: touch and words.

Imagine having a wordless conversation… it wouldn’t go very far, especially if it’s your first conversation, right?

Same thing with touch. Touch is very important because it’s how a woman feels you and feels whether she’s attracted to you.

There are 3 stages of touch that we teach at Introverted Alpha: 

  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. 

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 and you can see that she likes you so far, here’s what you can do depending on whether you’re sitting or standing:

  • If you’re sitting, you can lean in and touch her on the hand, arm, or knee.
  • 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 as they landed, she eagerly entered her number into his phone. It was so easy to touch her because he had all that zero-pressure practice with his attractive, already-attached friends!

Takeaway:

In summary, there are three steps 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 woman you’re attracted to doesn’t have to be daunting.

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. And as it resonates with you, sign up to be notified the next time it opens.

If you’d like to develop your own uniquely attractive vibe, download our free ebook on doing just that. Get all 22 pages for free right here.

Sarah Jones
Sarah Jones
Sarah Jones is founder and CEO of Introverted Alpha; the premier dating coaching company for introverted men; featured by Forbes, Business Insider, Cosmo, and more. Pick up your free copy of Sarah's 22-page ebook inside the blue box just below.

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