[X&Y] The Dreaded Question: "How Many Women Have You Slept With?"

Published: Sat, 05/30/26

Updated: Wed, 06/03/26

SCOT MCKAY'S DAILY TIPS FOR SUCCESS WITH WOMEN

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WHAT'S INSIDE:  How to handle the most dreaded question women ask.

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(FYI...The author of this thing is genuinely a good guy who 'walks the talk'.)

OK, now it's time to share something with you that I had way too much fun writing...


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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?

Be Good,

Scot McKay

X & Y Communications

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