Twice a year, this maximum-security prison hosts several dozen weddings

All photos courtesy of author

Tensions were running high in the reception area of the Oregon State Penitentiary on wedding ceremony day. Jo, one of the day’s many brides, had somehow fashioned an updo free of bobby pins so as not to send the metal detector howling. She had also stashed two backup outfits in the car in case the guards deemed her wedding dress — a black-and-red sheath from Rent the Runway — too formfitting. Anthony Behrens, the man who would perform Jo’s nuptials, fiddled with his dossier of papers to make sure all the documentation was in order. I hoped nobody would notice…

While serving a 25-year-to-life sentence, Ivié De Molina had a four-night honeymoon in a trailer

Photo by Nathan Dumlao on Unsplash

It had been 18 years since Ivié De Molina had been with a man. Arrested on her 28th birthday for murder, robbery, and kidnapping, she is serving a 25-year-to-life sentence at Bedford Hills Correctional Facility, a women’s maximum-security prison in Westchester, New York. Ivié posted an ad on the pen-pal site and received mostly disappointing offers from prospective men. (One fellow wanted her to send him her pubic hair.) Just before her ad was about to expire, Ivié received a letter from a dashing Canadian who seemed too good to be true. After 11 months of visits, letters, and…

The soul searching and questioning behind committing to the system

Credit: Liderina/iStock via Getty

Many people who end up in relationships with prisoners say the same thing: They weren’t originally looking for love. Jo, a military veteran and 44-year-old mother of three, was simply doing a good deed, she thought. Four years ago, she was dropping off old clothing at a friend’s church when she passed the prison ministries table. A volunteer urged her to send a warm holiday wish to a prisoner. She selected Ben’s profile from because he stated explicitly that he was only looking for friendship. They struck up a correspondence and discovered a shared sense of humor and undeniable…

The peculiar appeal of a prison pen pal

Photo by Najib Kalil on Unsplash

Maybe it’s hard for you to understand the urge to pick up pen and paper and write a prisoner you’ve never met before, be they a serial killer celebrity (like the one Samantha Spiegel sought out) or just your garden-variety drug dealer/car thief/conman.

But dozens of websites exist to introduce the free to the incarcerated., a site that serves as a matchmaker to potential pen pals, has more than 13,000 active prisoner profiles. Inmates pay $40 a year to post headshots as smoldering as anything you’d see on Tinder and to write profiles — you know, sharing their backgrounds…

What is it about handsome criminals?

Richard Allen Davis (L) in court with attorney Barry Collins (R). Photo by Scott Manchester/The LIFE Images Collection/Getty Images

Samantha Spiegel was 19 years old when she started writing letters to some of America’s most notorious murderers. A pretty art student with corkscrew curls and porcelain skin, she wasn’t hard up for a date, yet Spiegel wrote to locked-up criminals like Charles Manson, the Unabomber, and “Night Stalker” Richard Ramirez — a man who raped and murdered more than a dozen women.

“It’s not like I was in love with every murderer. I had standards,” she says today. “Scott Peterson is a douche. …

Elizabeth Greenwood

Author of PLAYING DEAD: A Journey Through the World of Death Fraud. Holler at @lizgreenwood4u

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