World's Unluckiest Bachelor? 6 Matchmakers, 250 Dates, and Larry Greenfield's Still Single. Here's Why..

Larry Greenfield: bad luck or bad in love?(Dennis Clark/Polaris)

Larry Greenfield can't understand why he hasn't met his wife. He's successful, single and he's not cheap.

In the past 12 years, the 47-year-old has spent over $65,000 dollars on matchmaking services, according to the New York Post.

Now 250 blind dates later he's still single and he's blaming his former matchmakers.

"You pay them up front and they don't provide a service. They tell you how wonderful you are, whatever you want to hear," Greenfield told The Post.

How to be a matchmaker for friends

The retired Wall Street trader seems to have approached his quest for a wife like a kind of business acquisition. "My job right now is meeting a girl," he says in the Post's now viral profile.

It's not exactly a romantic notion, but then neither is paying money for a set-up. But with his laundry list of requirements for a partner, Greenfield figured matchmaking was his best bet. It wasn't.

"His problem is he's a six and he wanted tens," Maureen Tara Nelson, one of Greenfield's former matchmakers, tells Yahoo! Shine. She claims Greenfield chose his dates through her based on photos and profiles but still came back unsatisfied. "He'd say there was no chemistry, but he picked the women!" says Nelson. Greenfield didn't respond to our request for comment at press time.

The Post, however, does paint Greenfield as a bit too detail-oriented. In addition to a woman who's slim, Jewish, and funny, he wants a "non-alpha"-someone who isn't committed to a career.

In New York, that type of women is increasingly rare, according to Nelson.

"He thinks because he's wealthy he could get a beautiful women, but what he doesn't realize is that beautiful women in New York are also already successful."

Millionaire Matchmaker candidate exposed as conman

Maxine Gordon, a 44-year-old comedian set up with Greenfield, echoes that sentiment.

"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 told The Post, after her first date with Greenfield was also her last. "He's looking for love at first sight, and everyone has imperfections. Talk to someone. Get to know them."

If Greenfield needs to lower his expectations with women, he may also need to change his approach to meeting them.

"Matchmaking might not be the right way for him to meet women," says Amy Laurent, a Manhattan matchmaker who recently starred in Bravo's Miss Advised. "It's no longer the days where older men looking for younger women can go to a matchmaker to buy their love."

Confessions of a millionaire matchmaker millionaire

"People who hire matchmakers for thousands of dollars generally want to avoid the vulnerability that we all face when we search for love, " says Nancy Slotkin, a matchmaker who Greenfield has reportedly set his sites on next. "Rejection is part of the process even for the best catches. High-priced matchmakers prey on people's fear of rejection and often make a lot of false promises."

Laurent agrees her colleagues sometimes get blinded by checks "waving in their faces," when they should be turning down overly picky clients who will never be satisfied with what they believe is a purchase.

Now that Greenfield's quest for love has gone viral, his luck with women may be getting worse. Imagine searching this guy's name before a date and coming up with articles like this one.

"I think it's going to make dating harder for the kind of woman he wanted, " says Laurent. "But maybe that's not such a bad thing--I believe everything happens for a reason."