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How To Initiate & Hold a Conversation With A Woman You’re Attracted To

Hold a Conversation With A Woman

The key how to initiate & hold a conversation with a woman you’re attracted to (no matter how beautiful she is) starts with controlling your mind.

You know what approach anxiety feels like… sweaty palms, racing heartbeat, maybe even an upset tummy.

And even if you manage to approach her, your body can work against you and sabotage your success even if you know all the best pickup lines.

It all starts in your mind. Your psychology affects your physiology!

When you master your mind, these conversational strategies will flow naturally, and talking with beautiful women will be a lot more fun!

And you’ll avoid making an all-too-common attraction-killing mistake many men make. More on that shortly.

So how to initiate & hold a conversation with a woman you’re attracted to starts with getting past stinkin’ thinkin’ so you can stop simping or not even approaching!

Hold a conversation with a woman…

1. Confidence

What is confidence?

Essentially, it’s you knowing yourself, liking yourself, respecting yourself, and being yourself.

You know your own good traits and less good traits you’re working on, and you accept the things you can’t change.

Confidence is also knowing you can handle the outcome of whatever “negative” experience shows up in life.


You finally approach a woman you thought was giving you the green light but get shut down in a nasty way.

It doesn’t affect how you feel about yourself because you know you’re the prize.

Your attitude, “Awesome, I just dodged a bullet.”

When you have confidence in yourself, it’s much easier to approach women and …

2. Break the Ice

Breaking the ice doesn’t need to be complicated or overly creative.

It’s okay to keep it simple! In fact, it’s usually better.

You really don’t need witty one-liners or overly creative conversation openers.

Example (this happened to me!)

“Hi, my name’s JP. You look like a nice person, I thought I’d introduce myself.”

It’s best to add something like, “I only have a few minutes but wanted to tell how what a nice smile you have” or “…how nice you look…” or some other sincere comment.

This type of introduction makes her feel safe. Your compliment isn’t sexual and you won’t be there for long.

If she’s standoffish, no big deal, tell her to have a nice day and move on.

But if she smiles or thanks you that’s a sign she may be open to conversation.

3. Conversation

After giving her a sincere non-sexual compliment, you’ll want to avoid an awkward silence by asking a simple question.

Pay attention to where you are and make an observational question about it.


If you’re in a coffee shop say, “I haven’t been to this coffee shop before, are they any good?” Or, “I come here often and haven’t seen you before, are you new to the area?”

Or, as JP said in the park, “You were really into your book and I didn’t know if I should interrupt you but you look like a nice person. What are you reading?”

Listen, be curious, pay attention to details, and don’t interview or interrogate.

And don’t feel like you have to fill all the silences. Non-stop talking just to fill space feels more awkward than a moment of quiet.

If it’s going well, you’ll want to sprinkle in some playful teasing to the conversation.

How to increase her attraction by teasing her playfully later but first…

4. Sharing

Sharing is caring.

So, you know I’ve said many times to always leave them wanting more.

But you have to give them enough to want more.

Find ways to introduce some emotional intimacy.

Emotional intimacy helps with bonding and trust.

Talk about your passions and interests and pepper in a little vulnerability.

Wait, what??


After you’ve chatted awhile and made her laugh or sincerely smile, you might say, “Hmm, you seem like a great girl/woman, you’re a heartbreaker aren’t you?”

So, you’re not saying, “I’m scared you’ll crush my soul” which would be weak.

But she’ll know the underlying meaning is you’re open to opening your heart, maybe to her, but what might she do with it?

Being open without being desperate is brave, not weak.

Key Point!

The difference between vulnerability that’s ooh-la-la sexy and vulnerability that’s a turn-off is where it comes from.

Vulnerably rooted in love and compassion is strong and sexy; a vulnerability that comes from fear is weak and not sexy.

The next tip on how to intimate & hold a conversation with a woman you’re attracted to is one a lot of guys get wrong.

5. Make her feel special (without simping)

If you do something she knows is especially for her, she’ll feel special.

Women want to feel special!

But overdoing it makes her feel cringe like you’re trying too hard because you don’t think you’re worthy of her.

The best way to do this is by limiting it to one action.


When you do this she’ll want to get closer to you, and if you do some of the other flirting suggestions (coming up), then it won’t be unexpected or uncomfortable.

This brings us to getting physically close… But first, let’s look at getting closer to her.

6. Getting close

Intimacy requires closeness, both emotionally and physically.

If you’ve done the lead-up correctly, you’ll already have a level of emotional intimacy that naturally lends itself to more physical intimacy.

Of course, you’re not going to go straight from sharing a vulnerability to making out—if she’s girlfriend material—but getting closer physically is a natural progression.

Again, more on teasing, flirting, and touching in a minute.

But by now you should be looking at her longer, holding eye contact, and if she reciprocates, slowly move in closer.

If she leans in or doesn’t move away or break eye contact, she’s enjoying your company and it’s safe to ask for her number.

Now is the time to leave her wanting more!

You can say something like, “Oh man, I’m going to be late…what are you doing to me, woman? Let me get your number so we can continue this another time…”

Strategies Employed:

  • Retraction close: You’ve got to be somewhere. (Leaves her wanting more.)
  • Not really a neg close: She’s to blame for being intriguing. (She feels desired.)
  • Assumptive close: You’re not asking for her number, you assume you’ll get it and see her again.

7. Just because you can doesn’t mean you should…

A critical point for a man learning how to initiate & hold a conversation with a woman you’re attracted to is ensuring true compatibility.

Just because you can have her doesn’t mean you should have her.

If you’re looking for your forever mate, make sure you know your deal makers and deal breakers, and don’t settle on the important things!

Follow your heart but take your head with you!

Be honest with yourself (and her), and if you have doubts, trust your gut.

To know exactly how to tease, touch and flirt with her to create instant attraction, you’ll want to watch my video on Teasing and Flirting.

Watch that one here!

Thanks for being here, God bless.


hold a conversation with a woman

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  1. I am very attracted to a woman who is half my age (I am 64) we are both into classical music (I am a symphony conductor and she is a very talented oboist) We are seperated by many miles (I am in the US and she is in Germany) I have been invited to guest conduct the orchestra that she is a member of next autumn. I am a bit nervous about meeting her and it is more than a year away. I am mostly concerned that if she rejects me that it might be seen as me being unprofessional. I really want to approach her when I start working with the orchestra, and I will only be there for 3 weeks. I would like to start a conversation with her when I first get there, so if it goes well, we would have time to nurture a relationship, but if it does not go well, I don't want to risk it looking like a workplace incident. Things are so complicated with women nowadays.

    1. It’s great you have a connection with someone who shares a similar interest. I’d caution you to worry less about getting rejected in a year and more about taking yourself off the market for that long on a ‘maybe.’ Get to know her in a casual, friendly, no-obligation way until you actually meet in person. If it evolves, fine, but there are risks to long-distance especially when you haven’t even met in person. In the meantime, watch my video on long-distance love. You got this!

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