Gentleman Scholar

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?)

Perhaps the least stressful way of carrying on with a woman not your wife is to self-medicate early and often. It may also be helpful to involve yourself with a woman you don’t actually respect, which is perhaps a sin within the sin, yes, but may help to simplify things. If we are just talking about getting cheap thrills, or about the quasi-quixotic pursuit of erotic novelty, or about numbing yourself against the terror of mortality—if, in sum, we are primarily talking about developing a relationship with an unfamiliar vagina—then it would be slightly less stupid for the cheating man to seek out a girlfriend for whom he is unlikely to develop the feeling of love (or one of its illusory doubles), on account of sharp differences in sensibility or social caste or what have you. Obviously, there are no guarantees here; the heart and the libido have been known to leap yawning gulfs, and the familiar erotic law of supply and demand only complicates the matter further. (Updike: “[A]ppealingness is inversely proportional to attainability.”) Obviously, also, it would greatly help a person attempting to enter an extramarital relationship in a spirit of premeditated detachment to be a sex addict or sociopath or narcissist (as opposed to a garden-variety horndog with a heart of gold or a standard-issue midlife-crisis victim with a romantic streak).

But I think you see my point: If we are talking about an affair that generates affection and recycles that emotional energy as fuel for its survival, then the time management issues you’ve brought upon yourself will be intensified by the fact of spending your days consumed with thoughts of the other woman as you scribble her name in your mental notebook and your nights lying in bed weeping copiously while necessarily hiding your tears from the wife you still love, which is not to mention the emotional demands that the girlfriend will make on you directly, nor the existential wear and tear of the shame and fear and thrill engendered by your fall.

Good luck!


I am a professional in my 30s and often find myself pausing when wanting to address a group of people of mixed gender and age, or solely composed of women, in a generic, somewhat casual, but still professional and appropriate way (whether in email or in person). It seems in fashion to call such a gathering “guys,” but I do not find it appropriate to say “Hi, guys!” or “Can’t wait to see you guys!” to a mixed group or to a group of women. It also sounds odd and patronizing to say “guys and gals/girls/ladies” to anyone except acquaintances whom I know will not be offended. With just men, I have no problem saying “guys” or “gentlemen,” and with female friends, have no issue with saying “ladies” or “girls,” but those don’t seem right in other circumstances. I often default to “folks,” but that seems forced. What, then, is a useful term for a gentleman to use for such a crowd, either mixed or solely female, in social and professional circles?

Thanks for your question. As Allan Metcalf mentions while discussing the utile y’all in How We Talk: American Regional English Today, the problem haunts us because we fell away from employing thou as a form of second-person singular address and reserving you as a plural: “We lost thou a couple of centuries ago, because thou didn’t seem as polite as you.” Metcalf further explains your irritation with you guys as a reaction against two aspects (“masculine reference and slang”). Meanwhile, Slate’s language blog heartily endorses your desire for a second-person pronoun singular in its indication of multiplicity, supposing that there is “something more intimate, more demonstrative, more direct, about making sure that pronoun is unambiguously plural.”

I hereby call upon this column’s readers to address this matter in the comments. Whaddaya say, gang? Any advice, comrades? Are any of yous willing, at this moment of rejiggering personal pronouns, to coin an American analog of ihr or ustedes?