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When Do You Flirt? When Do You Go Deep?

A lot of guys ask me what they should talk about with women after an initial approach.

As always there are two levels:

The Flirtatious

Depth

I happen to be a fan of mixing them up. When a woman asks me my sign, I usually say, with utmost sincerity, “Yield” or “No Exit” but then, if it’s important to them, add, “Gemini.”

There is a time to keep flirting – and keeping up the social tension – and there is a time to leave flirtation behind and meet a woman heart-to-heart, soul-to-soul. Only you can tell when you need to employ which mode.

Here is one clue on how to handle the transition, and as, always, it means taking the lead.

Say you are joking and flirting and messing around, but suddenly she injects some true depth into the conversation. Say she mentions she’s tired of being hurt – this is your sign to drop the flirtation and take her even deeper than she just asked you to be.

Here is an example from a text conversation I recently had with a

stunningly beautiful young woman who gets hit on constantly. I met her online, took her to a nice dinner. We had a blast – really funny and

smart girl – and we laughed our way through the whole thing. Our second date ended up in an unexpected (by me!) but very passionate encounter in her apartment.

The next day, we were lightly flirting by text -- when the conversation took a heavy, serious “real” turn. Now, before you read this, I want you to know that I am in fact, looking forward to finding one great partner with whom to journey into the next phase of my life. So my answers to her are all genuine and truthful. I want you to watch the modulation of flirtation and seriousness, and how I take her call for depth even

deeper…

Me: Mopster substitute (that’s her dog who joined us in bed unexpectedly)

Her: I will treat you as my grandchild, then.

Me: Yay! Cookies!

Her: But that is all you will get, if you are a bad boy. And maybe a time out.

Me: Yes, my dominatrix

(Any time a woman pulls “power” on me, I call her a dominatrix or say

“Yes Mistress” – to playfully alert her that this will not be an acceptable way of communicating with me. Also, if they “tell” me to do something, I reframe the statement into a question. For example: if she says, “Get me a fork.” I respond: “Would you like me to get you a fork?” I do it

playfully but I am very clear that I do not take orders – from anyone..

On the other hand, that I am happy to help when asked.)

Her: Hey! I’m your grandmother.

Her: Why are you talking to me like that? This is Mopster, talking!

(Here’s the tonal switch)

Her: Why do you like me?

Her: I don’t want to be a booty call.

Me: bc you are smart and funny and playful…

Me: … and nutritious Her: ok.

Her: you forgot psycho.

Her: how many women are you dating?

(Ok so that last one was a question from insecurity, and I don’t know what she is fishing for exactly – but I do know that it’s not really from her heart. I needed her to reframe this. So, not wanting to be

robotically answering her and following her, I decided to play a bit.

Otherwise, she would own me and lose respect for being too obedient.)

Me: 3 and a half.

Her: why half?

Me. Machete accident.

Me: But I got the good half, so it’s all good.

Her: You’re a nut.

Me: That’s why we go together so well. Also bc I’m so hot.

Her: No! I am the hot one!

Me: Yr acceptable Me: Yr the nerdy one.

Her: True, I am nerdy.

(Ok – so that was a little play, making sure she doesn’t pull her “hot”

card on me. I won’t fall into that position, of being submissive because she’s model-quality. Now, notice, here comes the switch again – but this time it’s for real. Please note, all kidding aside, this is a heartful,

beautiful good woman, speaking from her true heart, so I meet her there with the full power of my full authenticity.)

Her: Promise me you won’t hurt me – I’m so done being hurt Me: I respect that. Tell me exactly what you need.

Me: I really like you. So tell me everything you need and I will never lie to you.

Her: Don’t make promises you can’t keep.

Me: Got it. That’s #1. Deal.

Her: What do you want?

Here is where I let the flirtation go 100% and take her beyond what she asked for. I lay out my deepest desires in a truthful way that I know will lead her even more deeply into thinking about what I would be like as a partner. The key for you is to see that here I take the LEAD.

Me: A lot.

Me: Honesty. Depth. Sweetness. Laughter. Kindness.

Her: That’s me!

Me: Endless sensual bliss and deep connection

Me: The kind of love and connection, devotion and mutual celebration that poets write about.

Her: Sounds good.

Her: … and a huge walk-in closet.

Notice, I am not the one who broke the emotional tension of depth. She mentions the walk-in closet bc now she feels comfortable that I’m not a player or surface guy – that I really can offer the kind of coming-home-to trust she truly desires. Of course, I notice that she couldn’t stay in that very serious place. She was testing and is satisfied, but she didn’t go deeper with me. I’m watching closely now, to see where she goes.

What happens next is interesting. She had to go to work. Then, after a short while, after mulling what transpired, she continued the

conversation. Now remember, we had only gone out twice. I was

traveling across the country, so it’s a bit odd that we had this conversation by text, but hey, that’s 2011!

Her: I am looking for something serious, not play.

Her message was for real. So here, I ratchet up the stakes even more, because I know she is serious. She is testing me so I take the lead even more commandingly, raising the stakes and asking for something more by adding the word “extraordinary” and letting her know that she’s not only qualifying me, but I am qualifying her. No mistaking that here!

This is the voice of boldness that women want. It is the voice of Commanding Confidence

Me: Me too. I had my play. I am seeking one extraordinary woman for an extraordinary life

Me: I don’t do mediocre well.

Her: Do you want marriage again? Marriage till the grave? If not, please tell me now so I don’t get attached.

Me: Yes. Absolutely. For my extraordinary equal.

Me: But I am very, very picky.

Her: Good Her: Good

Me: I require reeeeeeealy deep and open evolution Me: A deep curiosity rather than arguing

Me: I don’t fight and I don’t hurt.

Her: Ok

Me: I want amazing love and daily celebration

Me: What do you want? What experience? Day by day?

Her: Someone who will make good on their word Her: Someone I can share all with

Her: The good and the bad.

Notice how I really gave it all. I opened both barrels. I wanted for her to feel my overwhelm. That I really meant it. That I held a high vision for love. As you may know from my other works, I take true intimacy very seriously, as a powerful spiritual arena – not just a convenient

partnership. So I have the vision to offer when a woman asks what she wants. I don’t give a standard offer. I lead her with vision and see if she can go that kind of distance with me. She left to go to work but when she poked me later with…

Her: Boo!

Me: boo? You already scare me.

Her: Good.

Me: Tell me your three best qualities as my beloved, worshipped wife.

Notice – here is a really great girl who has clearly been hurt and lied to in the past. We got very sexual very fast and now she was worried. I actually really liked her. So I was not going to mess around with her.

She wants to play for high stakes, I will meet her there – and that’s why I immediately began qualifying her and bringing her back to the depth of our previous discussion almost right away. I made a joke first so I don’t come off as psycho-serious – but then I took it right to “okay, you want marriage? I am going to be the best husband you will ever know (“my beloved, worshipped wife”) – so what are you bringing to the table.

I’m letting her know that I am indeed a serious man and suitor, but not in any way a pushover or an easy catch – most important – I’m not a follower and it’s not her decision alone. This assertive approach is especially important with especially beautiful women because most men just fall to their knees and do whatever they are told by them.