This must be one of the oldest and most considered questions of mankind.
I'm willing to pay well for an answer that is clearly backed up by
experience, with obvious good ideas and possibly some references to
classical sources such as literature. The question is how to enlist a
mistress from a considerably younger female connection - a good friend -
who is unattached and in need of money, but who would normally not consider
an alliance with you because of age and the fact that you are married. The
proposition has to be subtle because there is a strong desire to retain the
friendship if there is no interest. Just as important, the proposal has to
be such that it isn't perceived as payment for services.

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Request for Question Clarification by nenna-ga on 03 Aug 2005 09:03 PDT

Hello,

Are you looking more for personal suggestions or facts? I could write
you out a answer from a woman's perspective giving you information on
how to approach this, however, I can't find documented sources that
would back up your scenario. Let me know a bit more about what you're
looking for, and I'll see if I can help. I've also been talking to a
number of friends of mine in this situation (I know a lot of people
with alternative lifestyles) and getting 1st hand stories from them as
well that could help if you're looking for personal
information/suggestions.

Nenna-GA

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Clarification of Question by xclaire-ga on 04 Aug 2005 06:27 PDT

Firstly, I am still very confused about this process, and may be doing
the wrong thing, apologies if so. I really like the approach as
described by nenna-ga, it's not clear whether I am after 'facts' or a
more personal approach, and I'm not sure what is more appropriate. I
think the opinions of others are potentially very valuable, but that
of course'depends'. In response to other comments, no, there are no
children involved, young or otherwise. I have no moral qualms about
this question or associated background, and have put a great deal of
thought into the situation.

I also don't want this to go on for too long, and after another round
or so will be attempting to reimburse everyone as fairly as I can.

What an interesting question!  The condition that an answer must be
backed up by experience maybe asking too much, but if the posting
seems plausible, that could speak for itself.

First, win her affection, as in any affair, supported by subtle
generousity  - a "loan" to help with her financial straits  - no cash
-  paying her back rent or car payment, a bill for her expenses, or as
a participation in her work if she has a shop or the like.  If that
doesn't work, give up and be happy with retaining friendship.  In the
long run, that could be much more satisfying.
Dreams of what could have been are often much better than what
evolves, especially when the eventual consequences occur.

"classical sources such as literature":
David and Bathsheba,
Goethe's Faust,
Madame Bovery,
The Scapegoat,
My Life and Loves,  ...

none really very applicable, but I am sure that there are others that are.

Myoarin

It seems to me that enlisting a mistress from a friend is destined to
lead to disaster.  The friend will know, then others will know, then
your wife will know and your work will know.  Then the mistress may go
psycho on you and everyone will know.  Of course, your overtures could
seem subtle only to you and the whole thing could blow up in your face
without having had a mistress at all.  The stories of men burned via
mistresses are legion.  What a nightmare you are tempting.

According to Whois, mistress.com is owned by Digital Management, Inc.,
22433 Meadow Woods Cir., Taylor, MI 48180

Of course you didn't ask about mistres.biz or mistress.gov

Do you wish to retain the marriage ? If so, try being (reasonably)
honest, and tell the girl you value her friendship, that you'd like to
extend it to sex plus fun with no strings, but will understand if she
says no. Do it yourself - don't expect a friend to approach her for
you - that's pimping.

Be subtle about money. Tradition - apart from perhaps paying her rent
or education expenses - is presents and the occasional holiday (NOT
check-in to a hotel in order just to go to bed). Be gracious if and
when she wants to break it off, and generous with your farewell gift.

Do not spend money that will affect your family - if you can't afford
the membership of a good golf club, you can't afford a traditional 
mistress.

Don't take her to  business conferences unless you want the whole of
your industry to know within a week. No, they won't believe she's your
"niece".

If you are considering this because your wife is ill, be tactful and
considerate of your wife's feelings. Otherwise, should your wife wish
to take a lover, do not be either surprised or offended.

Age should not matter if you are reasonably fit, not very overweight,
and preferably have your own teeth (or at least teeth that stay in at
night). Don't sudenly jump into an over-strenuous get fit regime:
other things bing equal, it's a dead giveaway.

If you still have young children at home, I think you should reconsider.

Mixing both frendship and money/mistress requires a lot of
intelligence and maturity from the women. It will, for sure I think,
alterate the friendship but in the case the woman is very intelligent
and accept these conditions, it is something that should not be taked
about and remain unofficial between both persons, you and her. She'll
maybe understand that somehow, both friendship and the mistress
position, has its advantage at the condition you treat her like a
gentleman and protect her in a way that no other men did before. Then,
the friendship might turn into a real romance and even be more
dangerous, since she might expect from you not only that you support
her financially but stay with her. In the other hand, she also has to
respect your status as you have to respect her status, she is not
married and therefore, might have the right to date somebody elsed.
That's why it is tricky for both of you and even your own wife. But
believing that the friendship will remain the same as before, is quite
impossible I think

Thankyou, there is valuable advice in there. I'm attempting to find
out how to remunerate you with a fee that I judge fair. I think it is
likely that there will be no 'full'' answer to this question.

I was not aware that comments appear globally. There is more than one
response with good information.

Those people whose names are in black are ga members and can comment
but not answer questions.

Those whose names are in blue are official Answers researchers. 

If you feel one of their responses is worth your original fee, ask
them to post it as an answer.

Or if you feel the fee should be shared, you can change your amount
offered for the original question and ask one reaearcher to post their
comment as an answer, and then post some simple questions (eg. "What
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