SWM, 54, seeking gold diggers for secret trysts and blackmail

Once, twice, three times a charm for Greenwich investment-firm chief Stephen Dent. The married heir to the Dupont empire has been extorted three times through the online sugar daddy website SeekingArrangement.com. Dent, 54, whose fortune is estimated at $100 million, lost a mere $200,000 on hotel trysts and web chats with wily women who saw that this was one sugar daddy to milk. The cost of a potential Dupont divorce for marital unfaithfulness? Priceless.

In one case Dent spent $15,000 for sex with a sugar baby he met on the website, a fee which makes Eliot Spitzer's $1,000-an-hour downfall look like a bargain. But unlike Ashley Dupré, who didn't know she was shacking up with the Governor, three separate women involved with Dent sniffed a goldmine and went on to threaten blackmail by exposing his philandering ways unless he kept the checks flowing.

In March 2008, a Queens resident pleaded guilty to extorting $40,000 from Dent, who had committed lewd acts with his girlfriend. Dent went on SeekingArrangement.com again, and was blackmailed by an Ohio couple who took him for $100,000 by threatening to release photos and e-mails of the tryst. And according to court records, a third woman extorted Dent for $9,000.SeekingArrangement.com claims to be the premiere site for a mutually beneficial relationship. Open to both sugar mommies and daddies, the site describes its core market as "rich and successful. Single or married," with "no time for games," who are looking for a "personal secretary, secret lover, student, or a mistress for an extra-marital affair." The sugar babies are "attractive, ambitious & young, college students, aspiring actresses or someone just starting out," who seek a "generous benefactor to pamper, mentor" and take care of them financially. The site is free for sugar babes to join.

The whole idea is based on the belief that it's human nature for people to seek out younger, more attractive partners, while younger men and women are seeking more mature, financially stable partners. "While some in society may have laid down a set of unsaid rules about extra-marital affairs," reads the site, "who is to say what is 'right' or 'wrong'?"

Well, besides the obvious, here are a few things wrong with this reasoning:

1. There is no love involved in these arrangements. The younger girls fully know that they're using the men for money.

I met a man once who told me he had met his girlfriend through a sugar daddy speed dating event. The men had to prove their net worth as $5 million or more. The women had to prove that they were hot. Simple enough. Seems like they both knew what they were getting into. As they proceeded to date, the woman demanded that he keep taking her out to more and more expensive places. If it wasn't the hottest place in town, they were done. After putting up with the charade for awhile, he realized that what he really wanted was a relationship that involved human feeling and emotions. Some men, however (ahem Donald Trump), can keep the con going for much longer.

2. Expectations are imbalanced. While it seems like an ideal situation for the sugar babies, they're often put into compromising situations, forced to do things they wouldn't otherwise do because they feel like they're getting paid to do a job. The men feel like they own the women. Case in point, Dent referred to his women as his "slaves."

3. Extortion! Sure, some men just want arm candy, and some women just want a free dinner. If you're not looking for love, we're not going to judge. But in this economy, where everyone is scrounging for extra cash, it's not even safe to try your luck with the gold diggers. One extra-marital affair could end up costing you a whole lot more than an expensive meal. It just goes to show that money can't buy you happiness, but it sure can buy you a lot of embarrassment and grief.
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