Dating / Relationship Question and Answer


23 May 2001


Dating Two (or More) Women At The Same Time



With all the hassles, why would someone want
to date more than one woman? Frankly, there are as many answers
to this question as there are men! However, some very good
reasons are as follows:


* Women are picky – by
dating more than one you increase your odds of finding and keeping one
that you’ll be with for a long time.


* Women are competitive – Think your buddies are competitive? Try
being with more than one woman!


* Women love a challenge – The bigger challenge they perceive you
to be, the harder they’ll work for your exclusive attention.


* There is no “perfect woman” – each woman offers a unique set of
benefits and problems. You may find that by dating more than one at
a time, you’ll get a good mix of the benefits.


* You’ll get to know just what you do, and don’t want in a woman
– Especially if your dating experience is limited, having more than
one gives you a better understanding of what you want – and



* You always
have a “back-up” – As you get to know a woman, you’re going to
get “tested” [please see:
for specifics]. It’s good to have a back-up or two so you don’t have
to throw away those expensive theatre tickets!


*You Better Get a Calendar!


Believe me, you’re going to need this handy tool. The format of
the calendar doesn’t really matter, as long as you can keep
track of which days you saw a woman, and what you did, and when
you’re next available. You’re going to want to know when you’re
free in the future (to schedule dates), and to review what you
did with whom. Why do you want to know whom you did what with
when? To cover you tracks! You don’t want to be having a
romantic dinner with a woman only to blurt out, “Hey honey –
remember that trip we took to San Diego?” only to find out it
wasn’t her you went with!


A calendar also helps you organize your time. Let’s face it; free
time is scarce for everyone these days. You want to make the
best use of your time that you can. By scheduling your time, you
can use more of it in ways you want – like meeting and wooing
women! A calendar lets you visually structure your time. You
know you need time for yourself, your work and your fun – work
them in with your women. Even better, when possible (or
desirable), bring along one of the ladies as a combination
date/hobby time. Now that’s using your time effectively.


*Loose Lips Sink Ships!


Just because you’re dating two or more women, doesn’t mean you
should advertise it – unless of course, that works to your
advantage! Believe me, women have an innate sense about these
things, and will probably figure it out without you telling
them. It is far better to have some mystery here rather than to
have everything out in the open. This way, you are in better
control. Further, because of women’s competitive nature, they’re
going to try to get you to commit to only them – even if THEY
don’t plan to see YOU in the long term! It’s a woman thing – go


Woman will use subtle tactics to get you to drop the other women,
such as saying “You know, I wouldn’t be sleeping with you if I
knew you were with someone else!” Here, the assumption is, that
if you answer this statement, you’re assuring her that you’re
with her exclusively. She knows that you, being a man, are
probably not well versed in using these “verbal puzzles” to your
advantage, (and, you’re probably not!) You don’t want to
outright lie to her – she’s going to catch you and hold you
accountable for it! Instead, you’re going to re-direct the issue
by saying something like, “Yes, honey, I know you feel that way
because I understand you.” Then, drop the subject and move on.
You are specifically not telling her what she wants to hear, but
you are responding to her.


The second reason you shouldn’t feel compelled to “out” yourself,
is you haven’t committed to anything in the first place. You
didn’t promise her anything – did you? Men have a bad habit of
promising the world to get sex – and women know it. Don’t do
this! Don’t let her back you into a corner. To prevent her from
doing this, you’re going to need to establish the rules up
front. She is going to assume your monogamy far sooner than you


To set ground rules; let her know that you’re busy elsewhere. You
don’t have to always jump to answer the phone when she calls,
nor do you have to return her call the same day. Get actively
involved in your friends, your work, your hobbies, etc. Then
when you are with her, make it real, quality time – but don’t
get locked into a schedule – being with her every Saturday night
for example. Be sure to use that calendar we discussed


*What’s Good For the Goose


By the way, it’s not reasonable for you to be out hunting, and
for you to expect her to be home waiting for you! She may WANT
an exclusive relationship with you, but unless you’re willing to
give her that, you can’t reasonably expect it from her. That
doesn’t mean that she won’t be monogamous however. This is for
her to decide.


*Be Careful!


You need to protect yourself. Just like you use condoms every
time you have sex (you DO use condoms – right?), you need to
protect yourself in other ways too. If she sense that you’re
with someone else, she is going to just “stop by” to say hello,
or call at inconvenient times. You may want to make it a habit
of not answering your door unless you’re expecting someone. At
least, don’t answer when “Ms. Stripper” is over having a


Further, if she begins pressuring you to make a commitment, and
you keep her going along without one, she may become angry – or
worse, psycho! Be aware of your surroundings when you’re out to
make sure she isn’t following you around. Watch out for her
large family members too. It probably isn’t coincidence that you
ran into her brother or her friend while you’re out to dinner
with woman #2. Does this sound crazy? Maybe, but I’ve talked to
too many men where it’s happened. Watch your back if you choose
to date multiple women.


One more thing to watch when you’re dating more than one woman –
your wallet! Dates are expensive anyway, often costing $100 or
more. If you’re dating twice a week, this adds up pretty
quickly. You may need to be more creative on how you spend your
dating dollar. Memorable dates don’t have to result in a second
mortgage – you just have to be a little creative.


Yes, there are many problems with dating two or more women at
the same time, but if you use your head, watch your back (and
your wallet), and do some creative planning, you could be in for
the time of your life!