The Web makes it easier than ever to cheat—and easier than ever for cheaters to get caught.
We've all been there: Your late-night flirtation with one (or several dozen) of your Twitter followers has blossomed into something very close to love, and now you've been called upon to do something bold. Chocolates and flowers won't cut it, and an invitation to dinner seems antiquated. No, it's time to send her a picture of your penis.
Be careful now—this is a delicate moment in any budding romance. You could kill the mood by getting paranoid that your junk might end up all over the Internet. On the other hand, you don't want to regret this later. Hence the question of the day: Is it possible to send out photos of your body parts in a secure fashion, such that they're viewable only by the many, many objects of your affection but not the public at large? More generally, how can you—whether you're a Democratic congressman from New York, a Republican congressman from New York, a pro golfer, or an NFL quarterback—set up a liaison online without getting caught?
Short answer: You can't. The Internet was built for sharing, and if you send pictures, videos, or text to one person, you might as well cc: Andrew Breitbart. This is the paradox of the Internet-abetted illicit hook-up. Digital technology has made setting up a secret relationship easier than ever before. You can find someone to love on Craigslist, use your cellphone to snap and send her photographic evidence of your deep feelings, and then log on to Hotels.com to book a place to meet. Best of all, you can do it all from the privacy of your home or congressional office, all with your wife in the next room.
The trouble is, all these tools will record a trail of your misdeeds—there's your browser history, your phone's archive of photos and text messages, your damning e-mail inbox. If you're careful, you can minimize the danger that any of this stuff will leak. But being careful is inconvenient, and it's likely a turn-off to your paramours. Plus, however careful you are, you'll never eliminate the chance of getting busted. Call it Weiner's Law: As the volume of your X-rated tweets increases, the probability of your genitalia ending up on TMZ approaches 1.
Anthony Weiner, of course, was not a paragon of discretion, and there's a wide distance between what he did and what one might call the "best practices" of online cheating. Weiner contacted women on Twitter and Facebook, and used public photo-sharing sites like Yfrog to post his photos. None of these systems was designed for discretion—rather, they're all meant to distribute your bits far and wide, which is exactly what's happening to Weiner right now. The congressman was done in by one of Twitter's oldest design flaws—the ease with which one can send a public reply when trying to write a private "direct message." This is known as a DM fail. In Weiner's case, it proved catastrophic.
So, which tools should Weiner have used to conduct his affairs? Shortly after Weiner's press conference this week, a start-up called ProtectedPix began shamelessly (and effectively!) showering journalists with press releases arguing that, had the congressman used the new site, he might have "prevented the widespread viewing of his photos." I checked out ProtectedPix, and it does seem to offer several features that Weiner would have found handy. One feature lets you blur your photos for public consumption. Weiner could have sent out these fuzzy images of his boxers as trial balloons, then granted his prospective paramours access to his non-blurry ProtectedPix album once they gave him a thumbs-up.
Unlike other photo-sharing sites, ProtectedPix has several security features to prevent people from copying your photos. A ProtectedPix image can't be printed, downloaded, or copied and pasted. The site even has a way to prevent people from taking screenshots of your images, and an advanced feature called BusyHands requires that you hold down a combination of keys to show an image—the theory being that if your hands are on the keyboard, they can't reach for a camera to take a picture of the screen. Joanne Villani, the site's founder, told me that it wasn't only cheating scoundrels who would find ProtectedPix useful. People who are wary of posting their pictures on online dating sites, or who want to share snapshots of last night's kegger without worrying that they might be visible by prospective employees could also use the site. "It's an alternative for people who want to be a little more private and have a little more control," Villani says.
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.
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 Slate's technology columnist and the author of True Enough: Learning To Live in a Post-Fact Society. You can email him at email@example.com and follow him on Twitter.
Photograph from BigGovernment.com.