[X&Y] The Dreaded Question: "How Many Women Have You Slept With?"
Published: Sat, 06/29/24
Updated: Tue, 07/02/24
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WHAT'S INSIDE: How to handle the most dreaded question women
ask.
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THE DREADED QUESTION: "HOW MANY WOMEN HAVE YOU
SLEPT WITH?"
Who knows why I've never gotten around to writing a newsletter that
addresses this question before? After all, it's got to be one of
the most vexing moments in any man's dating life.
There you are, sharing a perfectly pleasant and possibly even
downright fun moment with a woman. Things are going swimmingly.
Then, as if out of the blue, she blurts out The Dreaded Question.
It's as if time stands still, the music stops, and in your mind you
hear that harsh sound of a needle scratching a record...just like in
the movies.
It's as if everything is moving in slow motion when she forms the
words.
"So, how many women have you been with?"
Your response, if you're fortunate enough to think quickly, might
be along the lines of, "Been with? You mean like...hung out with?
Oh, I don't know. I make friends pretty easily so...lots, I guess."
But she just giggles...feigning innocence. "No, silly. How many
women have you SLEPT with?"
"Uh...Well, I used to take naps with my sister and the cousins when
we were kids. Those Sunday afternoon family get-togethers really
wore us out, you know?"
But you're getting nowhere. And you know it.
Seriously, though. How on Earth do you DEAL with that question?
I mean it just BLINDSIDES you, doesn't it?
Well, I've got great news for you.
From now on you can not only be READY for The Dreaded Question, you
might even be able to USE IT to test and approve whether or not the
woman who asked it is a high quality woman who you can get along
with long term...or not.
Here's everything you need to keep in mind.
First of all, remember that in any interaction with a woman--no
matter how hot she is--standard, basic rules of human social
protocol should apply.
This means that if you're with a woman you barely know, say on a
first or second date, it's completely INAPPROPRIATE for her to ask
such a personal question.
Remember always, you don't owe ANYONE you barely know all the
answers to anything and everything they ask about.
With that in mind, I'd go so far as to say that when a woman asks
you how many women you've had sex with very early on it presents a
valid question of whether or not she has fully developed social
skills.
But there's more.
Bear in mind that The Dreaded Question almost NEVER can be answered
in a way that will make her happy anyway.
Too many partners? Not enough partners? It's a "lose/lose"
question any way you slice it.
Really though...what is the "magic number" she's looking for, anyway?
The "man whore threshold" is likely to be different for every
woman, and it can be pretty low.
Meanwhile, I get e-mails from men who are virgins and all but
convinced that if ANY woman ever found out about that she'd point
and laugh...shortly before running away.
The good news is that what those guys fear most would probably
never happen. Women just don't think in terms of male sexual
experience as a yardstick for heroism.
The bad news, however, is that if YOU are a virgin and SHE isn't,
as soon as she finds out she'll probably feel like a slut and
suddenly clam up and sulk for the remainder of the evening.
You'll keep asking, "What's wrong?" She'll keep answering,
"Nothing." Afterward, she'll never return your calls again and
you'll wonder what you did wrong.
How about if your "number" is just one or two? Good grief...even if
that's the plain truth do you think she's going to actually BELIEVE
it?
So then, let's get right down to it: How do you ANSWER THE
QUESTION, anyway?
Well, for starters, I'm not convinced that telling her exactly what
I just told you is a particularly bad strategy at all.
In other words, knowing that it's a "trap question" to begin with
why not just ask her point-blank what kind of answer she's looking
for?
Let her take responsibility for having asked the question and own
up to her intentions behind it, right?
You might find she backs down right then and there.
But she might not.
From there you can proceed in several different directions...and it's
all up to you which path you choose.
You can use the time-worn strategy of just giving her preposterous
joke answers until she gives up:
"Oh, 5,577...no wait, make that 5,578. I forgot one."
"Do all the times I was forced to perform sexual favors against my
will by gun-toting groupies have to count?"
"Well, let's see. There's my first cousin...and my other
first-cousin..."
"Do you want the answer I give my friends, or the one I give my
Mom?"
Now sure, you can amuse yourself to no end with this stuff.
But in the end, even though she might stop pressing for a real
answer, you've got to know she's probably going to ASSUME THE WORST
CASE SCENARIO--whatever that means for her.
So ultimately, you might be worse off avoiding the answer rather
than simply giving it.
That brings up a solid question in it's own right: Why not just
friggin' TELL her the truth?
You know what, that's a very real option. In fact, it's the option
that my co-host on the next episode of The Chick Whisperer (coming
in about a week) would recommend.
After all, it's part of who you are. If you're unashamed of your
amount of sexual experience, whatever it is, then answer the
question truthfully.
If you don't view sexual experience--or lack thereof--as a bad thing,
then you might not get along so well with a woman whose viewpoint
is different from yours anyway.
So yes...you might elect to just throw it all out on the table now
and get it over with.
But if you go that route, especially with a woman you don't know
very well, you're still left with the plain fact that you've just
answered what was an INAPPROPRIATE question to begin with.
So ultimately, my personal recommendation would be to go with this
simple, uncomplicated response that speaks VOLUMES: "So, would
the answer you're looking for include all the women I COULD have
slept with, but didn't on the grounds of principle?"
By answering as such, you avoid giving in to her lack of social
tact, but at the same time you subcommunicate that you are a man
who doesn't necessarily bang anything with a skirt on and that you
have a high standard of character.
Psychologically speaking, any woman who isn't neurotically obsessed
with the question itself should be impressed enough with that
answer to be satisfied.
After all, you've just subtly implied your own high standards while
at the same time exposing the inappropriateness of the question
itself.
And you've done it all without being defensive OR confrontational
about it. Outstanding.
To wrap this up, here are a few other quick notes on this whole
subject.
First of all, NEVER ask HER The Dreaded Question. It's equally
inappropriate for you to ask it as it is for her to.
Besides, you can't expect a rational, honest answer...ever. Women
with even a moderate amount of sexual experience are judged
ruthlessly in this culture (and in most others, also).
Going along with that, it's a BAD strategy to respond to The
Dreaded Question by turning it around with, "You first!".
It's a total coin flip as to whether that'll effectively sweep the
whole issue under the carpet or she'll actually GIVE YOU AN
ANSWER (which might not even be true).
If it's the latter, you're on the hook to give an answer
yourself...when you probably didn't want to.
Second, you might be wondering at which point in a relationship The
Dreaded Question becomes a bit more appropriate to ask. This might
shock you, but I'm inclined to say "never".
At some point we all as humans need to figure out that attractive
people tend to accumulate sexual experience over the years and
that's just the way it is.
Fretting over the sexual activity that happened BEFORE the two of
you ever knew each other is wasted energy.
And finally, consider this. Put the whole matter of social tact
aside for a second and consider what kind of woman would
proactively ask The Dreaded Question to begin with.
I mean, she's voluntarily opened that "can of worms" herself,
right? And she's got to know that if she GETS an answer, she'd
better GIVE one.
Put two and two together and you can reasonably assume that any
woman who drops that bomb is NOT going to have a very large
"number" herself.
Think about it. Even if she DID plan to give a lowball answer, few
people will voluntarily put themselves on the spot like that to
begin with...even if they plan to bend the facts.
Generally, we ALL feel uncomfortable when we lie...which is exactly
what polygraph tests depend on.
So if it's any consolation to any of you out there who might still
be clinging to the last vestiges of a "Madonna/Whore Complex", it's
the inexperienced women who tend to ask guys how many women they've
slept with.
Well, there you have it...a full-on breakdown of how to handle one of
the most classically awkward moments in dating.
Now that you've been armed with this info, will you dread The
Dreaded Question just a bit less from now on?
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