Computers, the new private eyes for cheating

Bad loving ain’t easy.

So many traps to fall into, so many mistakes to make, so many ways to flub up. Even the nation’s spy chief couldn’t get away with it, couldn’t keep a secret extramarital affair secret forever. If David Petraeus couldn’t do it, well, how could anyone else convince themselves they could pull it off?

But, you see, they do try. Every day. Their venues may sometimes be cliched — motel rooms or the back seats of parked cars — but their methods are often less prosaic. In the hunt for bad loving, some people will do almost anything.

Whole new identities are created. Elaborate banking labyrinths appear and disappear. Passwords morph, then morph again . . . then morph again. It all sounds so plausible, so utterly doable, at the time. Then, wham, some private eye with a video camera shows up and it’s all over (or, in Petraeus’s case, some guy with FBI e-mail peeping powers).

“Somebody’s going to make a mistake,” says Bill Mitchell, a private investigator and self-styled “infidelity expert.”

This digital world that we live in has made it only tougher on the unfaithful — not that they deserve a break, or anything, right? Each panting e-mail, each naughty text, each sneaky- ­rendezvous call is neatly logged with a digital signature. “Even when they delete everything, it’s still on the hard drive,” says Sandy Ain, a well-known divorce lawyer in Washington. “If computers are discovered during litigation or by an enterprising suspicious spouse, the information is readily available.”

Makes a person think twice about e-v-e-r-y single w-o-r-d he says — or types. “Unless you’re a Russian cybercriminal, anything online is potentially public,” says Paul Saffo, a technology futurist, or forecaster. “There are things in my life I would not write in e-mail but would say on the phone, but I wouldn’t leave on voice mail. There are conversations I’d not have on the phone, and those I’d only have in a field with no one around for a half-mile.”

It’s all about proportionality, he says. Online information is at risk, but “if you really worry about who can run up your tailpipe, before you know it you’re wearing a tinfoil hat on your head.”

But that’s what cheating spouses do. They worry.

The disposable cellphone is a new favorite mode of assuaging all that fretting and concealing all that bad behavior. See a man talking on one of those, and you might be seeing a “big sign of a cheating spouse,” says Jim Casteel, a private investigator in Birmingham, Ala., who has been chasing philandering spouses for more than two decades.

But the computer is the bigger tipoff, says Casteel; it’s the focal point of deception and the vector for discovery. Frequently, the men and women he chases set up dummy e-mail accounts under phony names, thinking they’ll avoid detection. But few can carry on without raising suspicions, and a suspicious spouse can turn into a resourceful one, he says. It’s common now, he says, for wary spouses to install spyware on their computers to surreptitiously track every keystroke and glimpse each Web site that gets visited.

“For every action, they’ve got a counteraction,” says Casteel.

What’s the worst-case scenario for those spyware-installing spouses? That would be AshleyMadison.com, a Web site whose motto is “Life is short. Have an affair.”

The site, which claims to get 1.8 million visitors per month, is a kind of electronic labyrinth of its own, designed, operated and maintained to keep cheating spouses safely inside and cuckolded spouses safely out. Servers are kept outside the United States for extra protection should, say, an FBI agent or divorce lawyer come knocking. “He could have used our site and called himself ‘Head of the CIA Guy,’ and do whatever he needed to do to focus on being the top spy, and it would never have revealed his true name,” says Noel Biderman, who runs the site.

Biderman says the future of infidelity-enabling technology is apps that allow people to sustain two personalities on the same device. “The next evolution is that most people will keep two devices, like two phones,” Biderman says. “One for personal and one for real personal.”

If technology is the problem, why not go back to the good old days? When people organized their illicit liaisons without accessing the World Wide Web.

“The old days of letter-writing and notes under the plants are bygone. People today are too impulsive. We are accustomed to instant gratification,” Ain said.

Indeed, 2012 cheating requires cleverness. And the more sophisticated the cheat, the more elaborate the scheme.

Casteel, the Alabama private eye, once chased a man who’d set up a parallel life with his lover in a separate town. They owned a house together and had a child.

All the while, his wife was buying a cover story that only a fertile imagination could conceive. The cheating hubby explained his long absences by telling his wife that he was on a secret mission. No tracking his calls — our national security depends on it! Or so she thought. His employer, he said, was the CIA.

He lied.

Manuel Roig-Franzia is a writer in The Washington Post’s Style section. His long-form articles span a broad range of subjects, including politics, power and the culture of Washington, as well as profiling major political figures and authors.
Michelle Boorstein is the Post’s religion reporter, where she reports on the busy marketplace of American religion.
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