Financing a Mistress
There’s no such thing as a free lunch; the same goes for free love — or, lust. Assuming you’re fit to handle the physical and mental demands of having a mistress, you best be set to spend dearly if you want steady action on the side. Financing a mistress is — ironically — a sizable commitment. Here’s a breakdown of a typical year’s worth of expenditures for your lovely lady on the side.
Basic expenses
Entertainment
Assuming she’s not into the clubs and concerts that don’t take effort and expense to get into (which also pose the greatest risk of exposure), you’ll be buying your way into some big-ticket shows several times a year. Quite a dilemma: You’ll want great seats, but you don’t necessarily want to be seen.
Cost: $3,000 (12 events, averaging $250 each)
Travel and transportation
Even legitimate business trips don’t have to be all business. If you want some breathing room and the chance to be together in public for a change, take her along to make downtime your get-down time. Naturally, take care expensing this “executive assistant,” “interpreter” or “independent consultant.”
As for transportation, this covers a lot of bases. It could count as an anonymous car you and your mistress use specifically for your engagements (registered to an LLC for good measure) or it might be cab fares and “you-didn’t-see-anything” tips. Clearly, the days of using your parents’ car for free transportation and carnal deliverance are long gone, and your mistress won’t take kindly to the gift of a bus pass.
Cost: $7,000 ($2,000 airfare for quarterly round-trip fares of about $500 each; plus $5,000 for car or cab fare and silencing tips)
Gifts
What’s an impractical risk of marital implosion without buying impractical goods? We’re afraid this isn’t a matter of whether she likes expensive gifts; it’s a matter of how often she requires them. Jewelry is probably going to take the biggest bite, though she’ll eventually ask for new furniture after her puppy (yes, the one you bought her) destroys her old set. Do we really need to remind you not to buy her a blender?
Cost: $7,500 ($4,500 for jewelry, $750 for the lousy mutt, $2,250 for new, non-puppy-bitten-and-defiled furniture)
Salon and spa
She wants to look good. You want her to look good. Any questions? If so, they’d better not sound like, “Why can’t you wash your hair and put cucumbers over your eyes at home?” If those words should ever happen to fall from your mouth, you deserve whatever befalls you afterward. Chances are, it won’t be pretty. Our advice: Shut up and pay.
Cost: $4,200 (Monthly salon and spa sessions averaging $350 each)
Cheating isn’t cheap…
Housing
If you’re meeting for trysts at a motel, you may as well put up your mistress in your guest house, complete with neon sign to attract as much attention as possible. Neutral, discreet ground is in order. An apartment is a wise investment. Even though it will require a sizable outlay, it’s potentially far less damaging than motel registration records.
Cost: $12,000 (Typical metropolitan one-bedroom apartment, plus utilities, averaging $1,000 a month)
Clothing
If you had your way, she wouldn’t own a stitch of clothing and she’d just pine for you in the nude. Look, you already have a mistress. Don’t push your luck. Invest in some designer clothing for her, and her pining will be for hardwood. FYI, Steve & Barry’s is not a designer label.
Cost: $6,600 (Averaging $550 per month)
extra expensesAs if all this weren’t enough, you have to consider the outside-outside expenses. These are truly rainy-day expenses, but that rainy day will come eventually. When it does, be ready for the extra payouts.
Extra expenses
Hush money
As discreet as you think you are, you’re bound to be caught by someone you know — or worse, someone you and your wife know. If you’re lucky, you can buy their silence. Simple opportunists will accept cash and be done with it. The truly despicable, however, may hold it over your head like the sword of Damocles, requiring frequent and demeaning favors.
Cost: At the very least, your pride
Damage control
You might think you’re being slick and perfectly devious until your wife gets suspicious. Don’t ask how she’ll find out. If we knew how that happened, we’d be selling the secret to the highest bidder. All we can advise is to be ready to go into pre-damage control mode. To appease a suspicious wife, it will take equal measures of tangibles and intangibles: “just because” presents, a trip to a place she’s always wanted to visit, a little extra attention, conversation and cuddling (just don’t overdo it or you’ll be dead obvious).
Cost: If you pull it off, less than half of your assets
Bear with us and do try to summon enough blood back to your brain for a few words about erasing the financial evidence. Even though the means to finance a mistress may not be an issue, the trail of ATM withdrawals and credit card statements could blow your cover. If you were already putting a little money aside when your marriage was peachy, you can use it to fund your extracurricular activities now that life with your betrothed is in the pits.
If you have nothing in reserve except your pent-up urges, the only laying you should do is the foundation for discreet finance. Have your company direct-deposit a portion of your salary into a secondary bank account you’ve established on your own. If your company grants a meal allowance or an expense account, work it — but don’t get greedy. Raises? Divert the difference into the account. Bonuses? Fail to mention or at least underreport it to the domestic authorities. If she doesn’t heavily screen your income taxes before signing, you’re golden. Otherwise, more than a few accountants receive calls immediately after couples sign off on their 1040s: “Um, by the way, when we were in your office, I forgot to mention…”
And the grand total is $40,000 and some change for 12 months of tappin’. That’s like buying a new BMW 3-Series Coupe every year. If you’re going to finance a mistress, you definitely have to pay to play. There’s no free lunch, and lust isn’t about to come your way gratis either.
Source: Private Media - 2007

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