A great post over at the Freakonomics blog.
A woman who takes [a sugar daddy's] offer is presumably already employed. Quitting her job in order to become a kept woman would mean putting her career on hold or abandoning it. Given the poster's self-description, it's safe to assume he has no intention of marriage or longterm financial commitment. So she is sacrificing a potential long-term career of her own for what might be a short-term financial gain with little guarantee of longevity.
Then, of course, there's the matter of satisfaction derived from the money itself. Just as a beautiful woman could be described as a “depreciating asset,” so could a rent-free apartment with an unlimited shopping budget. A platinum card may thrill for a few months, but, particularly given the required tradeoff of supplying sexual favors to a man who describes himself as “Danny De Vito with a nicer suit,” it's also likely to offer diminishing returns.
[...] There's also the possibility (increasing or decreasing depending on his age) that, at some point during the arrangement, he could become unable to work — he could get hit by a cab, or suffer a heart attack, or even be fired (perhaps for inappropriate behavior towards female coworkers?). His self-described unattractive physical appearance (not to mention loathsome personality, as exhibited in his posting) will reduce the likelihood that he will secure another high-paying job.
All of which leads us back to the conclusion put forth by the initial poster: if you're planning to gold-dig, stick to the “MARRIAGE ONLY” rule. Then, at least, you'll be entitled to equitable division of the spoils.
