The Curse of the Too-Picky Multimillionaire

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Love must be so easy for those with money, yes? We should know the answer to this already, but no. This week's lesson in romance economics comes by way of the New York Post, where much ink has been dedicated to the relationship travails of Larry Greenfield, 47, a retired Long Island securities trader who has spent more than $65,000 on six different matchmaking services that connected him with 250 women in 12 years. We wouldn't be talking about this, of course, if he wasn't still single, making the casual observer wonder if perhaps that's the state he prefers. Nor would we be discussing lovelorn Larry if he weren't on the pages of the official New York love tabloid, apparently by his own bidding.  

There is a cosmic and constant rule of the dating universe, and it is this: If ever you claim that there's no one good enough for you, that the 250 women (or men) you've dated are not right (and that whomever suggested you date those men or women not very smart or good at their jobs), the dating universe will strike back and call you "too picky." "Too picky" is the worst. It means you're not even playing the game right, or fairly; your standards and expectations are way too high and perhaps you are not as attractive or great as you think you are. Ouch. "Too picky" is an insult, rude beyond "that's the best you can do" and "you should just settle," though those are pretty bad, too. Maybe you just haven't found the "right person" for you, and that's O.K., really—the problem is when you start to blame other people for that.

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That brings us to Greenfield, who, as Tara Palmeri puts it in the Post, wants a woman who's "beautiful, thin, smart, Jewish, a sense of humor and from New York — but not an 'alpha,'” and  has been unable after 12 years to locate such a person. "Too picky" can also be a way of saying "What you want does not exist, maybe not for you, maybe not for anyone, and maybe you made this all up in your head and don't want it anyway." As if to prove that, one woman, "lovely business consultant and comedian Maxine Gordon" has come forward to speak out about Greenfield's dating issues in today's paper—the sad twist there is that apparently he snubbed her even though she says she's everything he's asking for and would still go out with him. This is all better conversation for somewhere besides a newspaper, but that's where it is:

“I think he’s looking for something that doesn’t exist: a gorgeous, talented, Jewish woman like Natalie Portman, except ‘I stay at home; I’m here to put on your slippers and clean your room,’ ” Gordon, 44, told the Post yesterday.

The question here, truly, is not why Greenfield can't find the right woman. Hey, it's hard out there! Or as he says, as a self-described "not bad" guy who hasn't "been to prison": "New York is a tough market for a guy like me. I thought I get the career, then I find the woman.... I’d trade it all in for a white picket fence, two kids, a dog. And you can have it all! I’d take a $50,000-a-year job, work until I retire." Yet, there's much he doesn't want, like a Knicks dancer, a too-artsy West Village girl, women who look "terrible," and then there's that alpha thing. Ugh! “I’m battling successful alphas, driven women who are very comfortable in their lives, and I get left in the dust,” Greenfield told the Post, adding, “My job right now is meeting a girl.”

There are some fascinating revelations to be gleaned about the alleged types of women and the men who date them in the two New York Post pieces covering Greenfield's mishaps and foot-in-mouth transgressions in love. And also, about dating styles. This, for instance, makes that guy with the sign look pretty sweet. But the greatest mystery about love is why someone would share their dating woes with a newspaper in this (or any) day and age. Pro tip: In order to find the person you want or think you want, avoid an unfavorable exclusive about the way you date in the New York Post.

This article is from the archive of our partner The Wire.