How To Date Rich Men


Forget everything you know about Donald Sterling. Yes, he’s a silly twat, but his woman is a conniving c-word. If she had nearly as many brains as vision problems, she would have continued wielding Don’s Black Amex card while she discreetly banged the United Nations.

If you’ve landed yourself a financial whale, I hope you selected one who isn’t too attractive (he’ll have too many other options), or too unattractive (they don’t make yet). You want one who’s somewhere in the middle. He may be a bit older, chubbier, shorter, or any combination thereof, within reason.

Things you need to know about Mr. Moneybags:

  • He knows you’re only into him because he’s loaded, but he’ll continue to fantasize that the mess he sees in the mirror isn’t a mess in the eye of his beholder.
  • He’s paranoid. He may be rich, but he still keeps receipts and reviews credit card statements.
  • If you’re hot enough, he’ll look the other way most of the time.
  • He’s probably banging other money-grubbing hosebags.
  • His friends and family will disapprove of you because he’s spending money on you instead of them.
  • He’s going to wear ridiculous clothing like Tommy Bahama shirts and Speedos. Refrain from commenting.

Now, a smart way to handle your Trump is to avoid saying you want something. You need to hint. Casually mention that you saw the lovely, white M5 the neighbor just bought his wife. Tell him Janice’s shoes look amazing on her. Recall that one time you got to taste Krug Rose on the beach in Cabo. You’ll be tapping into his millions in no time.

I need to break something to you, darling: He is going to expect to penetrate you, eventually. I know, I know. You’d think he’d settle for an occasional handy. Nope. You’re going to need to lube up and part your legs for ole saggy nuts. Just close your eyes and imagine he’s a dreamy lifeguard. Be careful not to grab marshmallow butt, or you’ll lose your lady boner.

If you don’t have a whale, and you’re tired of dating men with roommates, here’s some advice for harpooning one. First, you need to hang out in places they do. No more dive bars. Put on a skirt, and go to a cocktail lounge. The 19th hole at any fine golf course is a wise choice, as are restaurants that specialize in $100 steaks. You might also try business centers in large airports. Horse tracks usually have turf clubs filled with all sorts of Ferrari driving fund babies. You should also scope out the high-roller tables in the casino.

These men are easily impressed, but they have fine-tuned bullshit detectors. Best to be upfront about it, like a Brazilian woman. Smile, wink, and offer to be his candy. Laugh at his jokes. Admire his watch. Gush over his car (unless it is a Corvette). Tell your jealous girlfriends to fuck off, and proceed to enjoy your whale until he sinks.

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About the author

Author of humorous essays about relationships and lifestyles.