Anthony Weiner photos: The Web makes it easy to cheat, and easy for cheaters to get caught.

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June 9 2011 5:42 PM

Weiner's Law

The Web makes it easier than ever to cheat—and easier than ever for cheaters to get caught.

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Like all protection, though, ProtectedPix (which costs $10 a month) is a hassle to use. After all, it's hard enough to get a lady's attention with a plain old cock shot. Showing her a blurred shot, and then asking her to sign up for a ProtectedPix account that requires her to hold down several keys in order to see your penis, seems like it would be a few hoops too many. She might get the impression that you don't trust her.

This isn't a minor thing. The Internet is accommodating to casual encounters because it's both anonymous and convenient. The philosophy behind a site like ProtectedPix is that you should only share your photos with someone you've taken the time to get to know (enough time, at least, that she's willing to sign up for the site). It makes the flirtation slightly less anonymous and slightly less convenient than using Twitter alone—and, thus, slightly less fun.

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The site that has come closest to resolving this tension is Ashley Madison, whose simple mission—helping married people find people to cheat with—has earned it more than 9 million users since 2001. "The whole premise behind the site is that an affair has two key components," says Noel Biderman, Ashley Madison's founder. "One: A liaison with somebody else, and two, not getting caught." Ashley Madison has several technical ways to ensure that second part, Biderman says. When you leave the site, for example, you can not only delete your own account, but everything that you've sent to other Ashley Madison users is deleted from their inboxes, too. "We make it seem like you never existed," Biderman says.

He admits that these features can be defeated—people can print out or save your messages, or download your picture and post it on Facebook or some other less-secure channel. But that's where Ashley Madison's greatest security feature comes in: Everyone on the site has something to lose. Because it's a place where married people go after other married people, there's a kind of mutually assured destruction built into all romances. "When you see these men having affairs with people who don't have a lot to lose, is it any wonder you see them on TV telling their story?" Biderman says.

But if you go that route, remember that your browser history will show you've been checking out AshleyMadison.com. How will you explain that? And as your affair develops, you might get sloppy and start texting your mistress instead of messaging her through the site. And what about the hotel bills? Remember to use cash. Oh—and you better hope your wife hasn't installed a keystroke logger on your computer. Or discovered your secret e-mail address. Or hired a PI to trail you.

In other words, don't do it. There's no getting around Weiner's Law.

Farhad Manjoo is a technology columnist for the New York Times and the author of True Enough.