Multimillionaire Stephen Dent, an heir to the DuPont fortune, advertised himself as a sugar daddy on SeekingArrangement.com. He got several dates and then was blackmailed to keep his arrangement a secret from his wife. Police stopped the blackmailer, but Dent continued to use the website until more blackmail attempts began. In total, four people have been charged with trying to extort dent out of more than $100,000. Three of them have been convicted.
"You expect that when you have a Web site where you have lots of beautiful women and lots of rich men gathering," said Wade. "At the end of the day, you know, dating is a risky thing on the Internet, so precautions need to be taken."
Former prosecutor Wendy Murphy said that although the sugar daddy Web sites are legal, if money is exchanged for sex, then that's a crime.
"I don't know how you can call it anything but prostitution," she said.
Self-described "sugar baby" Miller disagreed.
"If someone wants to help me out financially, it's nobody else's business," she said.
Sexual advertising is hardly a secret these days. One only has to take a look at Craigslist's "adult services" classifieds section to see that. Even in the Yellow Pages, there are 20 pages of "escort" and "massage" services.
If this is illegal, then why is it out in the open like this? And why don't we hear about more prosecutions?
"It's a crime that not a lot of people care about," Murphy said. "[It] doesn't mean we should give up and just let it happen."
She argued that if everyone were to start robbing banks tomorrow, we wouldn't give up trying to prosecute those crimes.
But robbing banks steals from others. This behavior is different.
As far as the SeekingArrangement.com CEO is concerned, his site doesn't allow prostitutes.
"I draw a very clear line between what is prostitution and what isn't," Wade said.
So then, what is the difference?
"Just because a guy gives a woman money and sleeps with her doesn't necessarily mean it is prostitution," he said.
Gil agrees. He sees contradictions in what society deems to be prostitution.
"In 1955, my father made an arrangement with my mother," Gil said. "He put a ring on her finger and he said, 'I'm going to support you for the rest of your life.' So my father made an arrangement with my mother. If you make an arrangement for an hour, it's sleazy. But an arrangement for 50 years is OK. So, is it a time factor?"
But it's hard to deny that an arrangement for an hour is inherently sleazier than a marriage, right?
"An hour may seem sleazy," he said. "But when you take it a little bit farther into a day, a week, a month, then it appears to be a little better, I guess. You could call it prostitution or anything you want to, but I don't. Prostitution is just an ugly word for it."
"The concept that you trade your intimate sexual self for money is prostitution, if not slavery," Murphy said. "It's not a clear case the way slavery was, but it's darn close because of what's being sold: access to the intimate self."
However, Caplis, the single mother who said Seeking Arrangement improved her life, pointed out that sex is not always a part of the arrangement. One man she met through the Web site bought her a car, but they never had sex. They only talked on the phone and were never together in person.