Internet dating goes behind bars

Web's largest business pairs up with another huge industry: prisons

Marvin Span has been locked up for three years, his felony case tied up in appeals. In his online ad, he's draped over a faux-Grecian statue in what looks like the courtyard of his Rhode Island jail. He's "sincere, serious romantic and very intelligent and understanding." He's even, he writes - for the right woman - "willing to relocate."

Online dating, the Web's largest trackable source of consumer dollars, drew $300 million last year. Prisons, one of America's largest industries, are worth an estimated $40 billion. Maybe it was only a matter of time before the two paired off.

Their love story begins with the birth of the Internet: In 1996, as far as anyone can reconstruct, a handful of rudimentary prison-penpal sites started out with a few ads apiece. Today, convict matchmaking giants like and claim between 7,000 and 10,000 ads, and scores of competitors: from the straightforward ( to the suggestive ( to the uncomfortably mercantile.'s headline ad this week instructs: "To write to Diana, please add her to your Shopping Cart, then continue browsing ads or proceed to Checkout."

Some, particularly victims' rights advocates, oppose the ads. Others champion them as a humane way to keep inmates connected to society.

Many just wonder: What's the draw? Don't people without criminal convictions have a hard enough time getting dates? What would tempt a free woman or man to seek out and correspond with - and, as corrections officers say regularly happens, go on to date and even marry - an inmate?

The romance of lockup

Everybody's got a theory. Many psychologists say commitment-phobes pursue such matches. Others, like relationship adviser Gilda Carle, point out that far more women than men are involved with inmates. It's the "bad boy syndrome," she says: women attracted to not-so-nice guys out of rebellion, or low self-esteem. When someone who they know is capable of hurting others doesn't hurt them, she says, it "proves" they're special.

For Sheila Isenberg, author of "Women Who Marry Men Who Kill," it's more about pulp romance and daytime soaps. Guys behind bars have a lot of time on their hands: to write long letters, to compose love poetry, to perform a lot of the gallant, romantic rituals that modern courtship has largely lost. Inmate penpals aren't after casual sex, and they're less likely to judge a woman only by her looks.

For women addicted to the drama of Danielle Steele and Days of Our Lives, Dr. Isenberg says, prison dating is "Romance with a capital R. Every day is a cliffhanger. Is he guilty? Was he falsely accused? Will he be able to call tonight, or will there be a lockdown? A fight? A riot? It's a rollercoaster ride."

And they're not the only ones to whom prison looks romantic. Picture your own teenager's untied sneakers and baggy pants. Now think confiscated shoelaces and belts. Sure, prison culture's teen appeal stems in part from the fact that it's an obvious taboo, says Northeastern University criminology and sociology professor Jack Levin. But it's also a product of the same cultural forces that attract penpals to their epistolary cons.

"There's something in our culture that makes celebrities out of murderers and rapists, that promotes prison culture as pop culture," Dr. Levin says. "We do revere, respect, and admire power, and criminal behavior is a form of power."

In fact, notoriety seems to almost guarantee mail - and proposals. Serial pedophile John Wayne Gacy and serial murderer Ted Bundy both married women they'd corresponded with before their executions. In 1996, "Night Stalker" Richard Ramirez married in prison. Just last month, a personal ad on by Susan Smith, the South Carolina mother who drove her two sons into a lake in 1994, drew an estimated 1 million e-mails and letters.

That doesn't surprise Jennifer Drake, a 17-year Maryland Department of Corrections veteran. "Because if you can befriend Charlie Manson," she says, "if you can say, 'I'm Charlie Manson's girlfriend' - how many women can say that?"

Penpal sites make their money by charging inmates (roughly $40 to $75) to post their ads and print and forward any responses, or by charging penpals (usually less than $10) for inmate addresses. Few US prisoners are allowed access to e-mail or the internet, so most never see their listings. Some sites boast pages of testimonials: from soon-to-be- released convicts who've found love to death-row inmates who say letter-writing has given them a way to come to peace with dying.

Some states take an active stand against the sites. In 2001, the Oklahoma Department of Corrections issued "misconduct" citations to 51 inmates for violating the department's policy that "inmates may not directly or indirectly use any Internet services." Last fall, on the other hand, a California judge overturned that state's DOC prohibition against inmates receiving mailed printouts from the Web, calling the policy "arbitrary."

View from the inside

Ms. Drake, who for five years was assigned to read all her facility's incoming and outgoing inmate mail, says though the Web has greatly increased the amount of mail prisoners get, romantic attachments by penpals are an old story. But although her medium/maximum-security prison of 2,000 inmates saw an average of 15 weddings a year, she says, only a few of the hundreds of dating couples over the years struck her as long-term material.

"Because they really seemed to know each other," she says. "Sometimes they'd been through a couple incarcerations together. And he was honest with her when he messed up inside, and she didn't just say, 'Oh, honey, it's OK.' They were like regular couples, with the highs and lows." More commonly, Drake says she'd see an inmate "writing to four or five women, asking for money, stamps, visits, telling them all [that] they are the one."

That's what worries former Massachusetts State Rep. Donna Fournier Cuomo. The founder of a victim-aid group named for her murdered brother, Ms. Cuomo believes sex offenders, murderers, and people who've committed assaults should not be allowed to run ads. The owners of inmate ad sites, she says, should be taking a step back and asking: "Are we setting these people up to be victims in the future?"

Other victim advocates agree, saying the ads are disrespectful to those who've suffered at these inmates' hands.

Sandy Espinoza, president of jail and, says she knows how they feel: "My heart goes out to victims' families. I've had close family members murdered myself. But I also believe people can actually change. Not everyone," - the US prison population was 2.1 million last year; more than 95 percent will be released - "but some of the people in there are gonna come out and be loving mothers and daughters or fathers and sons - and maybe husbands and wives. Or they could be. And what a blessing to be part of that change for someone."

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