So here are the email parts, and my responses…

Quote from Jack’s email:

“I was a nervous wreck when I asked [S out] and I tried hard to come across as suave.. my hands were shaking. I was not very suave to say the least.. she likes Disney a lot right… so I think I asked her to be my princess.. ya. Also, I got it in my thick head that I should start writing her letters and sending her cards with secret msgs on them for her to decipher.. it really was a cute jester I suppose; I know she liked the letters.  She wrote me back several times.. the final letter I actually asked her out in it. Ya, no reply from that”

My response:

Awww Jack is so sweet.  I would never want to date him but he is still so sweet.

The term sweet is the kiss of death from a woman.

Sweet is equivalent to “he has a great personality”.

Get it!

Error #1

Never go through this amount of effort for a woman you are interested in if she shows no interest in you.

S is showing absolutely no interest in Jack and therefore behavior like this is uncalled for and wasted on S.

These behaviors and actions are for those women who are also interested in you.  The ones that can appreciate, reciprocate and reward your efforts.

Plus, these actions also make it painfully obvious to S that Jack really likes her.


Women always know when a man likes them.  You are not fooling any woman by being her “friend”.

Just because a woman has never mentioned or brought up the elephant in the room does not mean she is completely oblivious.

For S it is easier to ignore that behavior then confront it.

She wants to keep Jack in her life and having “that conversation” poses risk of loss.

For women it is always nice to have someone in their lives that cares about them, gives them attention, makes them feel wanted and lets them know they are still attractive.

Jack is that person for S.  He is her SAFETYMAN.

A safetyman is that man who will always be there for a woman.   The man that she knows will love her and treat her like gold and can always be an option in case it doesn’t work out with other men.

The sad thing about the safetyman is that he rarely gets called up to the majors.

This is because a safetyman does not stir feelings of attraction, he stirs feelings of comfort and security.

For women they fear that if they acknowledge this attraction their safetyman has for them and reject it, this security and comfort will be taken away from them.

Usually that is exactly what happens.

This is unhealthy behavior for both parties involved. Both are trying to avoid the uncomfortable conversation.


Do you know how much time and energy and money you are wasting avoiding this discomfort and possible rejection?


Here is another portion of the email from Jack that will show you exactly what will happen to you if you avoid this conversation.

“She was very infatuated with this new guy she met who told her he wasn’t interested and it broke her heart I suppose. At that point I pretty much got the ‘friendship’ card stapled to my forehead, as I became the chump that lent a shoulder to cry on. Although she keeps telling me how much she appreciated it and that she feels like she can tell me anything.”

As soon as you hear comments similar to the ones above coming out of the mouth of a woman you are interested in, RUN.

If I said before being called sweet is the kiss of death then being told “I feel I can tell you anything” is the torture chamber that comes before the kiss.

If you feel you are working a girl and she makes this statement count your losses and move on.

You have become the female confident equivalent.  Pretty soon she will be painting your nails and taking you on shopping excursions.

Error #2

Jack stayed in the game even though S was trying to make it painfully obvious how she felt about him.  She was telling him about other men and telling him she valued their friendship.

Jack was being dishonest to both S and to himself by remaining in the friendship.

Again, you have to take control, as a man, and ask for what you want.

The worst that can happen is that someone says no to your request. The good thing is that you know and you can move on to other options instead of being stuck in one option.

I know that working up the courage to ask for you what you want is not easy for everyone.  That is why the Wing Girls have created the program How to Become the Man Women Want.

Do you want to end up like Jack or do you want to be able to move on from dead end “friendships” to real relationships?
To ensure this doesn’t happen to you. Go to:

Remember, I’m here for you. I’m in your corner.