[X&Y Emily] How To Get Him To Ask You Out...Even If He's "Shy"

Published: Wed, 01/31/18

EMILY McKAY'S KEYS TO BLISS NEWSLETTER


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IN THIS EDITION:  Even when we're attracted to him and he SEEMS
attracted to us, sometimes things STILL don't segue automatically
to that magical first date.  Call it the "Dance Of Attraction".

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HOW TO GET HIM TO ASK YOU OUT...EVEN IF HE'S "SHY"


Hi Emily:


I love reading the newsletters!!  Wondering if you can give me
some advise.

Scenario:  I am new to this area I moved to for my job.  The
banker who deals with me in my business is very friendly and
single...YAY!

He is so sweet.  I am manager/designer of a florist shop.  I have
made some really terrific designs for him and he loves my work...
gushes over my work, really.  

He recently made an order for his mom and made sure I knew he was
single.  He said no luck with the last gal...LOL.

I told him he was lookin' at the wrong gals and called him sweetie
...for fun.  

He was very animated on the phone with me, complimenting me and my
work over and over again.  

Later on, a day or so later, he saw me in the grocery store and
actually bumped my cart with his basket while I was oblivious that
he was there...LOL.. surprise surprise!  

I smiled said, "Hey how are ya?" There was some chit-chat and
smiling...and then I left.  

The next day I called him to follow up on his mom's delivery.  He
thanked me over and over again and gave me the credit for the
success of the arrangement even though it was a wireout to another
florist.
 
My question is...should I email him and thank him for being so kind
as to say "hi" bumping into me at the grocery store, that he put
a smile on my face and that it was so nice to be recognized and
spoken to in a place where I am the stranger?  

Or...should I wait to see if he makes a move at the next business
after hours get together?  He goes to all of them.  

My way of thinking would be that a contact outside of work may open
the door for him to approach me if he is interested knowing that I
am open to him...hence the email, opening the door?

He might be more inclined to approach me then, right?  I think he
may be a bit gun shy right now as his last interest blew him off.

I just wanted to let him know I am approachable and interested in him.

What is the best way to do that without being too forward?  I want
him to know it is fine for him to come to me.  

I think in his position (VP at bank) he needs to feel that he took
the initiative, but also needs to know I am open to him that way, not
just in business.
 
Help!


Lisa (Ellsworth, ME)




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Hello Lisa:
 
Well, it sure looks as if he's interested in you, doesn't it?  Rest
assured, based on what you have told me I'm inclined to agree.
 
He has always made it a point to be nice to you, clearly enjoyed his
interactions with you, gone out of his way to say "hello" while
shopping and been genuinely glad when you've called him up on the
phone.
 
He has even "gushed" over floral designs, for Pete's sake.  Tell me
THAT isn't completely unnatural masculine behavior!  
 
The only thing he HASN'T done is ask you out.
 
Now I realize it's hard to imagine a successful business man
wimping out when it comes to asking for a date.  

After all, I think we all pretty much know already you're a
perfectly kind woman. In fact you seem super sweet...I'm all but
sure you deserve a great man!
 
I realize this is frustrating.  So let's get inside the mind of the
typical guy for a brief minute or two.  That way we can see what's
going on.
 
You mentioned that the last woman he was interested in "blew him
off".  Clearly he was somehow interested in relating that
information to you, probably to find out how you'd react.  

I think your response was a good one there, but believe it or not
he probably still saw it as ambivalent.
 
You see, most men are absolutely PETRIFIED of rejection.  

For a guy, becoming vulnerable to a woman he has high hopes for
romantically--only for her to turn him down--represents the
ultimate in pain and humiliation.  
 
In fact, I'm pretty sure most men would rather go to work in the
morning buck naked than to suffer being rejected by a woman flatly.  
 
And considering that the vast majority of them keep their clothes
on in the workplace (thankfully), that's saying something.
 
Moreover, most women--like you--understand that a man is more
comfortable when he has made the "first move".  Likewise, most
women also don't want to come off as "forward", lest they look
desperate or even "easy".
 
So what ends up happening is an "attraction dance" that often
involves a lot of sound and fury, but in the end goes NOWHERE.
 
You see, men are often creatures of logic.  Life is either black or
white.  Either you are interested (and are clear about it), or you
aren't.
 
Meanwhile, we as women are mistresses of subtlety, aren't we?
Indeed...we can flirt with guys in the smoothest of ways, only to
have it all go right over their heads!
 
But here's the crazy part.  You wouldn't believe the e-mails that
Scot gets from guys asking, "Why don't women just SHOW us they're
interested instead of making us figure it out?  Why can they just
OPENLY TELL US they want us to ask them out?"
 
The truth is, WE DO...ALL THE TIME.  And then what?  We feel
rejected ourselves because guys seem to completely ignore our
flirtation.
 
So there you have it.  It's not that guys are IGNORING us.  It's
that they don't TRUST our brand of subtle flirtation.  It's really
not their "language".
 
What's a woman to do?
 
Well...now that you understand how men often think a bit better,
you can become a bit more creative in how you communicate with
him.
 
Instead of telling him that he has been looking at the wrong
women, anchor the conversation to YOURSELF more directly by saying
that YOU aren't the kind of woman who would "blow off" a guy like
him, and that YOU realize he deserves better.
 
You may ask him what he is doing for a social life now that the
other woman isn't in his life any more.  When he responds, you may
suggest to him that he try some fun things that you personally
enjoy partaking of.
 
Best of all, you might simply come right out and tell him that you
are friendly and easy-going, and that you "don't bite".  From
there, he may finally get the message.  
 
If it seems like he's still having an internal "civil war" over
taking the plunge and asking you out, the absolute CLOSEST thing to
being "direct" while still not asking him out yourself, would be to
say to him with a smile, "Was there something you wanted to ask me?"
 
It's pretty amazing we have to go to such lengths with men
sometimes, isn't it?
 
But sometimes that's really what it takes.
 
So then, if you don't want to wait until the next business
after-hours social event I think it would be fine to contact him
again soon.  

I'd skip the e-mail and call him.  

Instead of saying it was "nice of him" to say hello at the store,
I'd tell him I was curious as to why he goes out of his way to
make conversation with you.  

Then I'd wonder aloud, "Is there a reason why you like talking to
me so much?  Is there something you've been wanting to ASK me?"
 

Have Fun,

Emily McKay
 


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