#1 Mistake Men Make When Flirting With Women (Not Listening)

I wanted to share a recent email exchange I had with an email coaching client of mine.

He has given me permission to share this exchange with you as he knows it will be a helpful lesson to you 🙂

I’m going to call this guy Bob and I’m going to show you an exchange he had a woman.

After I show you the exchange, I’m going to show you my comments to him on what I saw from a female POV…

As well as my interpretation of why his advances were not reciprocated.

Bob’s Email To Me & The Exchange With The Woman:


I would like to ask you if you would not mind passing comments on one of my online attempts recently. Any comments on refining and improving.

It kind of fizzled out, I think I let it dragged out too long at the end. Probably should have went for shorter messages and maybe just cut loose just after the initial rejection. Your thoughts?

………………online attempt………………

(Background: I knew this girl a little from before, I wrote to her complimenting on her latest photos I saw before trying to move to asking her out).

Me: I guess now is my only chance to flirt with you, before someone abducts you away ;). Seriously though the cream dress is just divine, really sensual and elegant.

Her: Don’t want to offend you but I’m not looking for a boyfriend. Friends are still ok. And thanks for the compliments. 🙂

Me: Hahaha, really? I knew I should have given Cupid his favorite candy before I left the house today. No problems with the compliments, it’s easy when telling the truth. 😉

Her: You are so sweet.

Me:….I was going to play hard to get dammit, and you had to bring up that one thing. I’ll have you know that I happen to be an expert in the use of sugar, and with it I can make a woman…..The rest is member’s access only 😉 and you can sign up for a special offer of $9,99!

Her: Haha, if I need a sugar woman I will let you know for sure! 😉

Me: I spent the whole day trying to puzzle out that message….I guess I’m a filthy degenerate because the only thing that makes sense to me, is us in a room with sexy sugar woman and then mercilessly licking her into a puddle, because why else would you want me to make you a sugar woman?? I think I’ve discovered a daaaaark place inside myself……. 🙁

Her: I hope you can cope with that by yourself!

Me: That’s so cruel….oh no, i think i feel something……;D

Her: Good luck

Me: Haha, I think you win, Can’t find a way to swing that

Her: Haha, okay. Hope we can still be friends though

***** end exchange****

Here are my comments:


So first, I’m going to comment on your style in this exchange.

I think you have banter pretty down.  Your responses were fun and playful.

What you DON’T have down, is listening and paying attention to the person you are bantering with.

You failed to notice that her responses were NOT on the same level as what you kept writing to her.  Women will always let you know which direction they want an interaction/conversation to go and their signals will be crystal clear if you just open your eyes and ears.

For example, if she was flirting back the same way with you and making similar references, associations etc….. I would say that this could lead to a pretty successful, fun first date.

BUT she wasn’t and didn’t.

Her first responses to you were actually extremely clear about her intentions and what she expected from you.

After your first message to her, she directly wrote “Don’t want to offend you but I’m not looking for a boyfriend. Friends are still ok. And thanks for the compliments. :)”

She couldn’t be any more clear with you. She saw the direction you were going and intention behind your message to her and she THOUGHT nipped it in the bud by sending you that message.

You responded well in that you still continued with confidence BUT then you kept pushing forward with your original intent. You went sexual when she clearly told you “nope. not into that. keep it PG please.”

A healthy, flirty banter would have been welcomed but escalating it to that level showed her you didn’t listen and therefore did not respect her or her wishes.

I have to give her credit because even though this happened, she was still polite.

She responded to you, but was still clear in her short responses that she didn’t want to push the interaction any further.

Now, I know your intent was not meant to be disrespectful.

I can tell you had no intentions of disrespecting her and you just wanted to flirt and get to know her better.

BUT you didn’t listen to her. You didn’t hear her requests and therefore she felt unheard and disrespected, hence the pulling back.

To help you stay present and connected to the women you are interacting with, I want you to practice using something called mirroring.

Here is how Wikipedia defines mirroring:

Mirroring is the behavior in which one person subconsciously imitates the gesture, speech pattern, or attitude of another. Mirroring often occurs in social situations, particularly in the company of close friends or family. The concept often affects other individual’s notions about the individual that is exhibiting mirroring behaviors, which can lead to the individual building rapport with others.

For now, if you can mirror the tone and cadence the women are using in their communication with you, it will help you stay more connected and show you are listening.

Your responses will come across better and attraction/connection can be built.

Another suggest I have for you is improvisation classes. Have you ever done improv classes??

In improv, the main rule is to work together to build a great story. If your goal is to be funny and get laughs, you won’t pay attention to what others are giving you and the whole scene will crumble.  You have to work together.

Same applies to every day conversation.

That’s kind of what happened with this girl. You didn’t play WITH her. You PLAYED past her, around her… however you want to phrase it.  But it didn’t work!  And therefore you missed out on ever “playing with her” in person 😉

Taking notice of this, mirroring and taking an improv class will definitely help you catch this behavior and stop it dead in it’s tracks so that you never lose out on an interaction again!


My advice to Bob is advice that I want to pass onto you.

I notice so many men doing this.  And not just my clients.  Guys that approach me!

Not listening to a woman’s communication makes a woman think she is being talked AT and not talked TO.

When a woman feels talked AT or like her words have fallen on deaf ears, she stops talking…gets deflated…and then gets angry.

Don’t make women angry!!!

Make them happy, aroused, excited, attracted…… All much better options that serve you 😉

Make sure to get your copy of The Chick-tionary.

The Chick-Tionary is a complete manual that beams a powerful light onto the most puzzling, perplexing & BAFFLING female behaviors… turning them all into confident clarity for you, and illuminating the simple steps to making her YOURS (for one night or for years to come).

Learn more here:


The Last Female Friend You’ll Ever Need,


More Articles