[X&Y] Dipping The Pen In The Company Ink [Reader Question]
Published: Mon, 12/15/25
Updated: Mon, 12/15/25
=====
WHAT'S INSIDE: Should you ask out a
woman you work with? Here's the definitive
answer...
=====
WHEN WHAT YOU THINK YOU KNOW
ABOUT WOMEN ISN'T WORKING
Masterclass For Men: "Hidden" Secrets To Success With Women
We've all been there. We read the books,
watch the videos...and they all seem to
repeat the same tired advice on women.
But then we go out there and actually
TRY what's talked about.
Crash and burn...again.
CLEARLY...there's a disconnect there
of epic proportion.
The problem is that sort of advice is
what gets us as men to click on it.
It's what we WANT to hear.
But we soon find out it's not what
WORKS.
Meanwhile, I realize men like you who
read this newsletter are here for answers,
not "infotainment".
You're already frustrated with the "same
old same old".
Not only are you ready for the TRUTH
you've never heard before anywhere
else, you DEMAND it.
If you've been reading (or listening to
the podcast) for even a short time, you
know I save you the fluff.
Here you can count on getting what's
proven in-field, not in marketing tests.
Not to get clicks, not to drive "viral"
traffic with controversy.
You can--and always have--expected
what really, truly flat-out GETS
RESULTS with women.
So for this month's Masterclass
For Men, I pulled out all the stops
and really had some fun.
I've spent hours scheming and
plotting EVERYTHING true about
how to successfully attract and
relate to women that NOBODY
else is talking about.
Basically, I've doubled down on the
counter-intuitive truth about success
with women...all in one fell swoop.
The result is an ALL-NEW slate of
field-tested and proven content you've
never heard before:
Masterclass For Men: "Hidden" Secrets To Success With Women
Remember when I launched "Yes,
And..." as a powerful way of meeting
women based on improv?
NOBODY had made that connection
before...yet is was developed straight
from hours upon hours of real, live
in-field interaction with women.
Now, imagine an entire Masterclass
chock full of similarly original, yet
POWERFUL steps you can take
RIGHT NOW to get better with
women:
Masterclass For Men: "Hidden" Secrets To Success With Women
Maybe it's because some of what
works sounds straight-up preposterous.
Or maybe it runs the risk of pissing
guys off who are just starting out.
Perhaps some might even find it
hard to believe, which is probably
why everyone else just avoids it
altogether.
But a WHOLE LOT of success
with women comes from counter-
intuitive mindsets, skills and habits.
And I, for one, believe YOU can
handle the truth.
Get your ticket to Wednesday
night's Masterclass For Men
and lift the veil on all kinds of ways
to attract women and relate to
them that virtually NO men will
ever figure out on their own:
Masterclass For Men: "Hidden" Secrets To Success With Women
Remember, the Masterclass
experience includes VAMANOS,
e-mail coaching and even a
live 1-on-1 Zoom call with me
personally.
Can't make it on Wednesday?
No worries. Get your ticket and
the Download Portal will be
ready shortly thereafter. Yes,
VAMANOS, email and Zoom
are still included.
=====
Hi Scot.
I'm a man who's just a bit confused by a response I got last
week when I asked out a very attractive lady. I asked her out and
got a "maybe" response.
So what exactly does that mean and how should I proceed if I want
to try again with her?
A bit of background...We work for the same employer, and see each
other about 2-3 times a week in the hallways. She's quite a bit
younger than me probably early-mid twenties (I'm 37).
Anyway, I've had several seminars/meetings which she's been involved
with. I always thought she was really cute from the first day I saw
her, but I'm sort of shy, so it took me a while to get up the nerve to
ask her out.
I went down to her office early last week to pass along some work
related information, but didn't have the nerve to ask her out then.
We've talked some at work, mostly about general stuff, just chit-
chat.
Had a two day meeting last Thursday/Friday and I made up my mind I
was going to ask her out. During the meeting, she sat across the room
from me and it seemed like she was flirting with me.
She'd flip her hair, smile at me a lot and place her hands the same
way mine were.
There were about 20-25 people at this meeting, so it wasn't too easy
to just go talk to her. I did some, just small talk, and finally I
decided to ask her out Friday.
I went up to her after the conference was over, and asked her if
she was seeing anybody. She said no, so I asked her if she'd like
to go out sometime.
Her response was maybe, so I said she knew how to contact me and
left.
She has been in meetings Monday/Tuesday, so I thought about trying to
maybe contact her Thursday. But I don't want to come across as being
pushy or anything like that.
Should I try to contact her first or wait a while and see if she
tries to contact me? I figured I'd ask her if she'd like to go for
a walk downtown one afternoon on break and/or maybe ask her out to
lunch one day.
What's the best way to do this so I don't get the dreaded "no" or
another "maybe" answer?
I could find an excuse to go to her office, but there are other
people around and it makes me nervous enough when I'm asking
somebody out without having other people around listening in.
Would a phone call be a better way of doing this? I've thought
about asking some of her co-workers about her since I'm friends
with some of them, but I'd rather just ask her myself.
I hope you can give me a quick bit of advice.
The "maybe" answer was one I haven't heard before. I'd almost
rather she'd have said no.
Is "maybe" just her way of saying she's not interested without
saying no? Or could she also be shy and just not sure about
dating an older guy?
From what I've seen of her, I think she might be shy.
Thank you!
Jay--Parts Unknown
=====
Thanks for writing, Jay.
I'll address the most obvious issue first. Since she's a co-worker,
I'd avoid dating her altogether because of the potential complexities
involved.
The old adage about "dipping one's pen in the company ink" applies
here. Basically, the assumption is that your career is too important
to sacrifice at the alter of having to deal with someone on the job
that you are involved with or (worse) were involved with.
At best it's a distraction for both the two of you AND your other
co-workers when things are going well between the
two of you.
But should you ever suffer a bitter breakup, not only will work
become a nightmare, you may find she sabotages your career either
consciously or unconsciously in some petty way.
Let's just tell it like it is. With over three billion women on
Earth, you'd do well to find one that doesn't work in the same
office as you do.
And for the benefit of others reading, what I've just said goes
DOUBLE if whoever you have your eye on is either a subordinate or
a client.
All of that said, I fully realize almost none of you reading this
are likely to pay any heed to logic.
Surveys still show that "the workplace" is the second most common
place for Americans to meet their future spouse.
(By the way, "introduction from friends or relatives" is still in
first place, with "online dating" in third place but rising fast.)
It's my contention, however, that the whole "pen/ink" factor is
pretty much moot in this case.
Sure, it's altogether possible that SHE may be more wary of dating
a co-worker than you are. That could indeed be driving this.
Or, perhaps she was looking for more definitive leadership from you
after she gave you that tentative answer. Some women really want
to see a bold, confident move even in the face of a bit of
resistance.
That's rather rare among mature adults, however. And for what it's
worth, if that's what was going on then the mood would have had to
have been decidedly playful as opposed to cold and direct.
But that aside, my gut feeling is that if she were all that
interested in you romantically, she would have made sure the
straightforward conversation you started with her about going out
sometime would have resulted in firm plans.
That didn't happen.
As such, her giving you "maybe" as an answer comes off as a
purely manipulative tactic that puts her in the driver's seat
insofar as decision making goes.
She can now take her sweet time to figure out what the relationship
between you and her should be.
If she wants, she might even attempt to control you to the end of
meeting whatever non-romantic needs she has (job related ones,
even? Ouch!) by perpetually "dangling the carrot".
Either way, the bottom line is that despite her flirtation during
meetings, she's not enthusiastic about going out on a date with you.
The ideas for follow-up that you've suggested almost never lead to
increased attraction on her part, which is really the missing piece
of the puzzle.
There's not much of a point to asking co-workers about her since
you've already talked to her directly. Such only makes your business
everyone else's.
Ultimately, I really would recommend looking elsewhere for someone
to go out with.
My general impression is that you don't deserve this sort of "game
playing", yet she's been straight-up rude to you.
If you see the world as rife with female possibilities, you will
not have such a pronounced need for this particular woman.
The irony is that once that is a reality for you, even women you
work with start coming on to you first.
But who needs them, really? You'll have opened up a far broader
How cool is that?
=====
(c) X & Y Communications LLC, 2025. All Rights Reserved.
Forward this newsletter to a friend, and help
build this worldwide movement of over 100,000
men reclaiming their masculinity, standing as a
positive role model and deserving the high
quality women we want.
The Definitive Facebook Group For Men
woman you work with? Here's the definitive
answer...
=====
WHEN WHAT YOU THINK YOU KNOW
ABOUT WOMEN ISN'T WORKING
Masterclass For Men: "Hidden" Secrets To Success With Women
We've all been there. We read the books,
watch the videos...and they all seem to
repeat the same tired advice on women.
But then we go out there and actually
TRY what's talked about.
Crash and burn...again.
CLEARLY...there's a disconnect there
of epic proportion.
The problem is that sort of advice is
what gets us as men to click on it.
It's what we WANT to hear.
But we soon find out it's not what
WORKS.
Meanwhile, I realize men like you who
read this newsletter are here for answers,
not "infotainment".
You're already frustrated with the "same
old same old".
Not only are you ready for the TRUTH
you've never heard before anywhere
else, you DEMAND it.
If you've been reading (or listening to
the podcast) for even a short time, you
know I save you the fluff.
Here you can count on getting what's
proven in-field, not in marketing tests.
Not to get clicks, not to drive "viral"
traffic with controversy.
You can--and always have--expected
what really, truly flat-out GETS
RESULTS with women.
So for this month's Masterclass
For Men, I pulled out all the stops
and really had some fun.
I've spent hours scheming and
plotting EVERYTHING true about
how to successfully attract and
relate to women that NOBODY
else is talking about.
Basically, I've doubled down on the
counter-intuitive truth about success
with women...all in one fell swoop.
The result is an ALL-NEW slate of
field-tested and proven content you've
never heard before:
Masterclass For Men: "Hidden" Secrets To Success With Women
Remember when I launched "Yes,
And..." as a powerful way of meeting
women based on improv?
NOBODY had made that connection
before...yet is was developed straight
from hours upon hours of real, live
in-field interaction with women.
Now, imagine an entire Masterclass
chock full of similarly original, yet
POWERFUL steps you can take
RIGHT NOW to get better with
women:
Masterclass For Men: "Hidden" Secrets To Success With Women
Maybe it's because some of what
works sounds straight-up preposterous.
Or maybe it runs the risk of pissing
guys off who are just starting out.
Perhaps some might even find it
hard to believe, which is probably
why everyone else just avoids it
altogether.
But a WHOLE LOT of success
with women comes from counter-
intuitive mindsets, skills and habits.
And I, for one, believe YOU can
handle the truth.
Get your ticket to Wednesday
night's Masterclass For Men
and lift the veil on all kinds of ways
to attract women and relate to
them that virtually NO men will
ever figure out on their own:
Masterclass For Men: "Hidden" Secrets To Success With Women
Remember, the Masterclass
experience includes VAMANOS,
e-mail coaching and even a
live 1-on-1 Zoom call with me
personally.
Can't make it on Wednesday?
No worries. Get your ticket and
the Download Portal will be
ready shortly thereafter. Yes,
VAMANOS, email and Zoom
are still included.
=====
DIPPING THE PEN IN THE COMPANY INK
Hi Scot.
I'm a man who's just a bit confused by a response I got last
week when I asked out a very attractive lady. I asked her out and
got a "maybe" response.
So what exactly does that mean and how should I proceed if I want
to try again with her?
A bit of background...We work for the same employer, and see each
other about 2-3 times a week in the hallways. She's quite a bit
younger than me probably early-mid twenties (I'm 37).
Anyway, I've had several seminars/meetings which she's been involved
with. I always thought she was really cute from the first day I saw
her, but I'm sort of shy, so it took me a while to get up the nerve to
ask her out.
I went down to her office early last week to pass along some work
related information, but didn't have the nerve to ask her out then.
We've talked some at work, mostly about general stuff, just chit-
chat.
Had a two day meeting last Thursday/Friday and I made up my mind I
was going to ask her out. During the meeting, she sat across the room
from me and it seemed like she was flirting with me.
She'd flip her hair, smile at me a lot and place her hands the same
way mine were.
There were about 20-25 people at this meeting, so it wasn't too easy
to just go talk to her. I did some, just small talk, and finally I
decided to ask her out Friday.
I went up to her after the conference was over, and asked her if
she was seeing anybody. She said no, so I asked her if she'd like
to go out sometime.
Her response was maybe, so I said she knew how to contact me and
left.
She has been in meetings Monday/Tuesday, so I thought about trying to
maybe contact her Thursday. But I don't want to come across as being
pushy or anything like that.
Should I try to contact her first or wait a while and see if she
tries to contact me? I figured I'd ask her if she'd like to go for
a walk downtown one afternoon on break and/or maybe ask her out to
lunch one day.
What's the best way to do this so I don't get the dreaded "no" or
another "maybe" answer?
I could find an excuse to go to her office, but there are other
people around and it makes me nervous enough when I'm asking
somebody out without having other people around listening in.
Would a phone call be a better way of doing this? I've thought
about asking some of her co-workers about her since I'm friends
with some of them, but I'd rather just ask her myself.
I hope you can give me a quick bit of advice.
The "maybe" answer was one I haven't heard before. I'd almost
rather she'd have said no.
Is "maybe" just her way of saying she's not interested without
saying no? Or could she also be shy and just not sure about
dating an older guy?
From what I've seen of her, I think she might be shy.
Thank you!
Jay--Parts Unknown
=====
Thanks for writing, Jay.
I'll address the most obvious issue first. Since she's a co-worker,
I'd avoid dating her altogether because of the potential complexities
involved.
The old adage about "dipping one's pen in the company ink" applies
here. Basically, the assumption is that your career is too important
to sacrifice at the alter of having to deal with someone on the job
that you are involved with or (worse) were involved with.
At best it's a distraction for both the two of you AND your other
co-workers when things are going well between the
two of you.
But should you ever suffer a bitter breakup, not only will work
become a nightmare, you may find she sabotages your career either
consciously or unconsciously in some petty way.
Let's just tell it like it is. With over three billion women on
Earth, you'd do well to find one that doesn't work in the same
office as you do.
And for the benefit of others reading, what I've just said goes
DOUBLE if whoever you have your eye on is either a subordinate or
a client.
All of that said, I fully realize almost none of you reading this
are likely to pay any heed to logic.
Surveys still show that "the workplace" is the second most common
place for Americans to meet their future spouse.
(By the way, "introduction from friends or relatives" is still in
first place, with "online dating" in third place but rising fast.)
It's my contention, however, that the whole "pen/ink" factor is
pretty much moot in this case.
Sure, it's altogether possible that SHE may be more wary of dating
a co-worker than you are. That could indeed be driving this.
Or, perhaps she was looking for more definitive leadership from you
after she gave you that tentative answer. Some women really want
to see a bold, confident move even in the face of a bit of
resistance.
That's rather rare among mature adults, however. And for what it's
worth, if that's what was going on then the mood would have had to
have been decidedly playful as opposed to cold and direct.
But that aside, my gut feeling is that if she were all that
interested in you romantically, she would have made sure the
straightforward conversation you started with her about going out
sometime would have resulted in firm plans.
That didn't happen.
As such, her giving you "maybe" as an answer comes off as a
purely manipulative tactic that puts her in the driver's seat
insofar as decision making goes.
She can now take her sweet time to figure out what the relationship
between you and her should be.
If she wants, she might even attempt to control you to the end of
meeting whatever non-romantic needs she has (job related ones,
even? Ouch!) by perpetually "dangling the carrot".
Either way, the bottom line is that despite her flirtation during
meetings, she's not enthusiastic about going out on a date with you.
The ideas for follow-up that you've suggested almost never lead to
increased attraction on her part, which is really the missing piece
of the puzzle.
There's not much of a point to asking co-workers about her since
you've already talked to her directly. Such only makes your business
everyone else's.
Ultimately, I really would recommend looking elsewhere for someone
to go out with.
My general impression is that you don't deserve this sort of "game
playing", yet she's been straight-up rude to you.
If you see the world as rife with female possibilities, you will
not have such a pronounced need for this particular woman.
The irony is that once that is a reality for you, even women you
work with start coming on to you first.
But who needs them, really? You'll have opened up a far broader
(and more private) world of new possibilities outside the
workplace. How cool is that?
=====
(c) X & Y Communications LLC, 2025. All Rights Reserved.
Forward this newsletter to a friend, and help
build this worldwide movement of over 100,000
men reclaiming their masculinity, standing as a
positive role model and deserving the high
quality women we want.
The Definitive Facebook Group For Men
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