Online dating, the Web’s largest trackable source of consumer dollars, drew $300 million last year.



In 1996, a handful of rudimentary prison-penpal sites started out with a few ads apiece. Today, convict matchmaking giants like prisonpenpals.com and jailbabes.com claim between 7,000 and 10,000 ads, and scores of competitors: from the straightforward (inmate.com) to the suggestive (ladiesofthepen.com) to the uncomfortably mercantile. Cellblockmail.com’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?

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.

More here.