Advice for men: How to keep a mistress, and the second-person-plural problem.

How Does a Gentleman Keep Both His Wife and His Mistress Happy?

How Does a Gentleman Keep Both His Wife and His Mistress Happy?

Answers for modern men.
Feb. 26 2014 3:50 PM

Cheat Sheet

Philosophy for philanderers.

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Troy Patterson.
Troy Patterson.

Photo by Christina Paige

Do you have any useful advice on how to maintain a mistress as well as a wife, in a civilized fashion? Not including the obvious “don't do it,” of course! Thanks.

Thank you for your question. Barred by its terms from strenuously advising restraint, I find myself inclined to bask in its shadiness and, simultaneously, to treat it as a prompt for a session of creative problem solving, as if this were a gifted-and-talented brainstorming session or an entry-level job interview at a management-consulting firm.


But I will assume that you are a veteran adulterer who has already resolved certain fundamental issues regarding discretion and self-deception and dissemblance, perhaps even taking an improv class to develop your talents for ad libitum mendacity, so I’ll instead step back and remark that this is one of those instances where it would be exceedingly advantageous to be exceedingly rich. For instance, you may find it helpful to settle upon your wife a trust guaranteeing her a Darcy-sized income—loads of free money in something like perpetuity. Given vast geographical disparities in the cost of living, one hesitates to prescribe a specific dollar amount, but the sum must glaze her scorn-washed eyes so that she looks the other way from all but the most rabid tomcatting and, further, nurture her sense that she will remain financially secure even should the madness instantiated by your skirt-chasing metastasize into a wholly debilitating infirmity.

On the real estate front, a city-dwelling two-timer should be on the lookout for a country house in which his spouse may comfortably pass the month of August while he is scratching carnal itches in the torrid town. It would be nice to find a place with an eat-in kitchen, a screened-in porch, and a gunite swimming pool, and it will be necessary to keep your mouth shut should the maintenance technician appear to be checking the pool’s pH levels with the frequency of a hypervigilant NICU nurse monitoring vital signs. Meanwhile, a suburbanite should consider investing in a no-fuss urban crash pad for himself, as in the 2012 Magnetic Fields song:

Where's a minx get minks to wear?
Why, my husband's pied-à-terre!
In two drinks, you think she'll care—
That's my husband's pied-à-terre!

In terms of ready cash, what you want is lots of it, some loaded into a prepaid debit card. These funds will come in handy whenever you feel yourself compelled to buy flowers and jewelry and swim noodles for your wife (when abruptly bludgeoned by guilt) or to fling 50s at cabbies to just keep driving around (while you and your girlfriend defile his backseat).

Let’s call the other woman your girlfriend, yes? One is not certain that mistresses still exist. That term tends to flounce in an antique fashion, to seem very bonbons-and-bodices. The most recent person recognizable as a mistress might well be Maria Ruskin, the special friend of bond trader Sherman McCoy in The Bonfire of the Vanities. I have a hunch that the real McCoys of 2014 do not have mistresses—except in those instances that the term mistress encourages the illicit couple in the useful idiocy of seeming to elevate their piggish bourgeois rutting to the truffle-scented aristocratic decadence of Louis XV and Madame de Pompadour. No, bond traders step out on their wives these day with girlfriends and side pieces and sugar babies and, in certain Scorsese-addled instances, goomahs. Not incidentally: Because our plan calls for you ideally to get exceedingly, consequence-cushioningly rich, I suggest you emulate Sherman McCoy and get a job in high finance. (Sure, there are also piles of money to be made in the tech sector—but has the relatively young corporate culture of Silicon Valley developed a tradition of perfidy to compare to the generations-deep institutional amorality of girlfriend-friendly Wall Street?)