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T h e F i v e Q u e s t i o n s E v e r y
W o m a n S h o u l d A s k B e f o r e
S h e G e t s i n T o o D e e p
I
had just gotten to Hollywood and I was seeing a lot of
things my then thirty-eight-year-old eyes had never seen
before. One of those that stood out most was the lifestyle
of a famous and well-regarded celebrity, whose name I’m just
going to go ahead and keep to myself. But this much I will tell
you: this man had it all—money, fame, and a bevy of super-
beauties so bad he could have easily made Hugh Hefner scratch
his head and wonder how he could get in on
that
action. I mean
this man was surrounded by gorgeous women. A lot. All. The.
Time. And I was amazed at this because I couldn’t understand
how one person could get all of these fine women like this. I
mean, he wasn’t the best-looking dude in the business—there
were others with more money, more prestige, and certainly
better looks than him. Still, he was a master at keeping a stack
of solid tens at all times, with commitments to none of them.
I’d heard about these superplayers with supermodels on their
arms and everything, but when I saw it up close, I was amazed
at how the actual connections could happen, and especially
why these women stayed with this guy, knowing that they
were one of many hanging on his arm.
And I needed to know how this was done (um, not neces-
sarily so that I, too, could have supermodels hanging on my
every word, but because I was genuinely blown away by the
phenomenon). So I sat down and talked to this guy and a bunch
of other men who were in similar “relationships” and asked
them point-blank: How do you keep these women coming
back for more? And each one, including the most notorious of
the bunch, laughed, shook his head, and said pretty much the
same thing: those women want the money, the fame, and the
lifestyle, and they’re willing to put up with a lot of things—not
many of them good—to get it. “But do they realize,” I asked in
all earnestness, “that this is going nowhere?” The one guy
shook his head some more and said, simply, “They don’t know
where it’s going because they never ask.” He added: “What am
I supposed to do—tell them I’m just using them for sex and arm
candy? It just is what it is.”
Blew me away.
And the more I asked the same questions of guys in similar situ-
ations, I heard the same answer, again and again. And each time I
asked them what could have made it different for the women they
were with, almost down to the letter, each one of those men said
the same thing: if a woman came to me and quizzed me up front
about my intentions, they would have known from the beginning
that I’m not looking for anything serious. They don’t ask, each one
said, because they think they’re going to run me off, so I get to just
string them along. And the one celebrity who seemed to be the
master of all of this said, quite simply, “I have enough of them so
that when I get the questions, I don’t have to answer because for
every one woman who asks, I have two more who won’t.”
Call this what you want: foul; wrong; inexcusable—what-
ever. But that’s how it is. And this kind of thinking from guys
isn’t just happening in celebrity circles, trust me. It happens
with everyday guys—doctors and lawyers, truckers and deliv-
erymen, too. Some of them have as many women as some of
my celebrity friends, and the women they run game on are just
as fine as some of the supermodels clinging to the arms of stars.
But if you’re a woman on a string of three or thirty-three,
you’re still on a string. And both you and I know that’s not a
good place to be.
Your objective is to avoid being on the string.
The first step, I think, is to get over the fear of losing a man
by confronting him. Just stop being afraid, already. The most
successful people in this world recognize that taking chances to
get what they want is much more productive than sitting around
being too scared to take a shot. The same philosophy can easily
be applied to dating: if putting your requirements on the table
means you risk him walking away, it’s a risk you have to take.
Because that fear can trip you up every time; all too many of
you let the guy get away with disrespecting you, putting in
minimal effort and holding out on the commitment to you
because you’re afraid he’s going to walk away and you’ll be
alone again. And we men? We recognize this and play on it, big
time. Know this: the game is old, and it’s not ever going to
change. My sons will do it the same way because they can and
there will be women who allow it to happen. But you can cer-
tainly know the rules up front, and change up your strategy, so
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