The week of February 14, 2016
HTTP LOVR written across two sets of knuckles

The pen pal romances of

By Zachary Crockett

On a waning summer day in 2015, Deanne Wilson flipped open her white MacBook and began the long, methodical process of finding a soulmate.

For the 42-year-old single mother, the afternoon ritual began as it always did: She started with OkCupid, then skimmed through, eHarmony, and Zoosk, rejecting hopeful suitors at each juncture. Then, she spotted something unfamiliar: a sidebar ad for a website called Intrigued, she clicked through.

Profiles of prison inmates lined the page, each listed with a photo, age, sexuality, religion, and crime committed. The men extolled their virtues in 250-word bios—“loyalty,” “honesty,” “great bod”—hoping to connect with a pen pal from the outside world.

Among these profiles was Alberto, a meaty, tattoo-emblazoned man with thick-rimmed glasses and a dark goatee. His crime, aiding and abetting murder in the first degree, had landed him life without parole in a Texas prison—but he wasn’t ready to give up on finding love.

“Ladies: Indulge me for a second while I peak your interest,” he wrote. “Allow me to explore your secrets and treasures … I will be your shining light.”

Wilson was smitten. “When I saw this man—this hulking, sexy man—and read his profile, I thought to myself, ‘I guess all the good ones are in prison!’” she says. “I was intrigued, so I decided to write him and take a chance.”

She emailed Alberto via the website, which then printed her message and mailed a copy to him in prison. Three weeks later, she received his reply in the mail. From there, the conversation went analog: the Internet, computers, and email—all off-limits to Alberto—were replaced by snail mail and semiweekly phone calls. “It’s like being in a relationship from a hundred years ago,” says Wilson. “You’re waiting by the mailbox for letters. Everything is so slow.”

Deanne Wilson is one of thousands of women who find love through prison pen pal websites. Many don’t begin with explicitly romantic intentions. More typically, pen pal relationships spawn from curiosity or a desire to make an meaningful change in an inmate’s life, and only over time become something deeper.

For those who do find true love behind bars, it’s a strange, unconventional journey, filled with unique challenges and barriers. What’s it like to fall in love with someone you’ve never met—to form a romance based solely on letters and the occasional phone call? To find out, we spoke with dozens of romancers and inmates, as well as the man behind the largest online prison pen pal site on the Internet.

A Google search for “prison pen pal” yields hundreds of websites; some advertise as strictly platonic (,, while others (, more overtly cater to hybristophilia—the attraction to “bad boy” types.

The largest of these sites,, was launched in 2000 by Adam Lovell, a Volusia County, Florida, former lifeguard and EMT. He considers it a streamlined way for the nation’s 2.1 million incarcerated men to strike up platonic friendships with the outside world. “We don’t advocate dating; it’s just a unique little byproduct of what we do,” he says. “A lot of the men on our site go in looking for love, but the romantic stories are rare.”

Regardless of motivation, getting a profile on WriteAPrisoner is pretty straightforward: An inmate writes to the website, which responds with an application and a thick brochure containing “rules, guidelines, and tips for writing a good profile.” Once submitted, the information—a 250-word biography and a photo—is published to the Internet, alongside a contact address and the crime committed. From there, it’s up to fate; with no way to initiate contact, prisoners must patiently wait for letters.

For this service, inmates pay a one-time fee of $40, plus a $30 yearly renewal. WriteAPrisoner currently has 12,986 profiles listed—91 percent of whom are male. Good-looking inmates (especially women) get significantly more mail, Lovell admits—and those with profile pictures are almost twice as likely to be contacted as those without them. Still, he insists he’s not running a dating site, but rather a “correspondence service.”

Lovell’s even crunched the numbers to support his case. Last year, he analyzed his website and found that romantic profiles (i.e., containing keywords like “Seeking Ms. Right” or “searching for my soulmate”) were, on average, 86 percent less likely to get mail than those seeking friendship. He warns inmates to tone down the “romance” language—yet hopeful Romeos persist.

“I like thick women because I work out but all women can reply,” writes one six-foot-three-inch, 245-pound inmate. “You must be a considerate woman who is full of passion and willing to fit me in.”

“Behind every King stands a Queen,” proclaims Jamuri Scott, a 37-year-old inmate in California. “I’m waiting for that one to take my hand, open her heart and give trust and life a chance.”

Fortunately for these men, women do give inmates a chance—and when fate smiles, it leads to love.

A convicted murderer serving a life sentence, Matthew Davis had been in prison for 12 years before trying out an online pen pal service. Initially, his hopes weren’t high.

“I just thought I might find a woman who was infatuated enough to send me some money—someone I could just use and not be emotionally attached to,” he says over the phone from prison. “I expected to find some superficial relationship that would never go beyond a letter.”

Just a few weeks after his profile hit the Internet, a young Illinoisan named Krista Hughes wrote to him—at first, just to offer companionship. Over the next eight months they formed what Hughes calls “an unexpected emotional bond.” Now they’re engaged.

Many prison pen pal romances play out this way: They begin innocently and platonically, then—typically within 4 to 6 months—transition into something deeper.

Heather, a 46-year-old divorced mother and pediatric nurse, came across WriteAPrisoner accidentally, in the course of Googling a friend’s criminal history. A self-described “caretaker” at heart, she decided to try out the service as a way to “make a difference in someone’s life.” But first, she set some ground rules: She wouldn’t use her last name. She’d get a P.O. Box in a neighboring town. She’d only select an inmate who committed his crime a long time ago, and who lived in a faraway state.

Her first selection was Kirk*, a man eight years her junior. “I figured he would consider me an older woman—not someone looking for a boyfriend,” she writes via email. “[Plus], he was pictured with a dog, indicating he was well-behaved.” Heather “pretty much stalked him online to make sure he wasn’t a psychopath.” Soon enough the two became friends, bonding over spiritualism. Several months later, Kirk expressed an interest in learning the ways of Buddhism, and Heather decided to use WriteAPrisoner’s religion filter to find a fellow inmate who could serve as a teacher.

“On paper, he looked VERY VERY SCARY, but in his picture he looked VERY VERY HANDSOME.”

It was in her “late night travels” through the site that she spotted “Ryan” (also not his real name), a life-without-parole inmate in California. In a strange way, she found herself drawn to him.

“On paper, he looked VERY VERY SCARY, but in his picture he looked VERY VERY HANDSOME,” Heather says. “And lo and behold, he was a Buddhist.”

Despite some reservations, Heather decided not to judge Ryan’s capital offenses. And he began to reveal a sensitive soul through his letters. “He started sending me some things he had written in the past about his childhood, about his studies, just about his path in general,” she says, “and I started opening up to him a little bit more, being more trusting.”

Heather—a woman who grew up in a sheltered Baltimore, Maryland, suburb, had her first kiss at 17, and funded her way through college by singing telegrams—soon found herself falling in love with a man far removed from her parents’ expectations.

“I was like and what the fuck am I supposed to do about this?” she says. “Why would I want to enter a relationship that is pretty much engineered to be difficult? I’d have to deal with distance, expenses…NEVER being able to make love. Why on earth would I do this?”

But she also admits it’s “the healthiest falling in love” she’s ever experienced—precisely because it’s analog.

“Our time is meted out to us in hours per week, so when we are present with one another we are fully present,” she says. “Then there is the fact that he will never get on my nerves by leaving his underwear on the bathroom floor. And the fact that I do what I want to do, and go where I want to go—which is nice at 46.”

Ondina Canto, a native of Providence, Rhode Island, and a mother of two young boys, tells a similar story over the phone.

In 2003, as coursework for her criminal justice degree, Canto, then 21, was asked to start a pen pal relationship with a prisoner. Growing up, she had always “had a thing for the bad boy type,” she says, and she seized the unique opportunity to “get inside the mind” of a criminal.

After browsing various pen pal sites, she settled on Shawn*, an inmate at California’s High Desert State Prison. He had just been convicted of offering protection to a prostitute and was a few months into a 16-year sentence for “pimping and pandering.”

“It was the way he worded his profile that got me,” she says. “He’s very intellectual, very smart. It was like he read an entire thesaurus.”

Her new relationship immediately attracted skepticism from friends and family. “Everyone had an opinion about my relationship: You’re an idiot. You’re wasting your time. There are plenty of men out there,” she says. “But it’s because of all these barriers—not in spite of them—that this has been the deepest connection I’ve ever had in a relationship.”

Thirteen years later, Canto and Shawn are still together. To this day, they have never seen each other in person—partly because of financial reasons (flights from Rhode Island to California are not cheap), but more so because they haven’t considered it necessary.

“We’ve formed that old-school romance through letters and phone calls,” she says. “My other relationships were always centered on the physical; with him, it’s all mental—we know each other from the inside.”

Shawn is set to be released in two years; before then, Canto plans to move to California and purchase a home near the prison. But the couple faces steep challenges: Shawn will be registered as a sex offender, rendering it difficult to find work or even take her children to soccer practice.

“We’ll make it work,” Canto says. “We’ve waited 13 years already. How much harder can it get?”

Jessica* initially set out to connect with a military pen pal through Adopt a US Soldier, but after that fell through, she chose to write a prisoner instead—strictly for friendship.

She recalls being “extremely nervous,” and concerned about soliciting someone “weird and crazy.” After weeks of combing through profiles, she kept coming back to the same page. “He wasn’t old, too young, and he didn’t commit a terrible crime,” she says, “so, I just took a chance.”

Gabriel* had been arrested in May of 2010 after crashing his car into a police cruiser—a crime punishable as “assault with a deadly weapon.” Three years later, in July, he received his first letter from Jessica.

“Our first letters to one another were three pages front and back; his second letter to me was 19 pages front and back,” she says. “It was so interesting getting to know someone through pen and paper: We talked about our entire life from birth, our goals and achievements, our positive and negative pasts—every single thing you could ever imagine.”

Two months of intense letters commenced; these segued into weekly phone calls and, a year later, monthly 7-hour contact visits. Gabriel is due to be released in 2.5 years, and the couple plans to build a life together.

“It’s weird—I never expected something like this to happen,” she says. “I just let things fall into place.”

Graph by Zachary Crockett; based on data from (*% Christian = non-denominational)

But like any romance, prison pen pal relationships can go awry.

In her late 30s, after a string of failed relationships, Mayra Ruiz, a nurse’s assistant in New York City, had grown weary of the dating scene and began to look for another way to meet men.

“I’m a good Dominican girl—never been in trouble, nothing,” she says over the phone. “The men I was meeting in the outside world were all pigs. They just wanted the physical, all the time. They didn’t care for me as an individual. They didn’t care to listen, or talk, or be romantic. They just wanted easy access.”

A close friend who’d been dating a prisoner suggested Ruiz try out a pen pal service. Around Valentine’s Day 2013, she decided to give it a shot.

The first man she connected with—whom she now calls “Bonk”—seemed genuine and kind. For months, he inundated Ruiz with passionate love letters. “He threw around the word ‘soulmate’ a lot,” she says, admitting that his language had her swooning. Then, things began to take a turn for the worse.

“It started with him asking me for money for stamps,” she says. “Then it turned into money for soap, money for food, money for things I didn’t even [think] he needed.” When Ruiz refused to transfer Bonk $400, the inmate sent her “the nastiest, meanest letter” she’d ever read. Eight months into a seemingly blissful relationship, he ceased communication and she never heard from him again.

Of course, romances—whether successful or not—are a small minority of all the connections made through WriteAPrisoner. Founder Adam Lovell has compiled stories from 360 long-term couples, all of whom met through his site. But for a website that facilitates thousands of letters per day, that’s a pretty low number.

But it does tell us something: Despite the challenges, love can flourish in the most unconventional of places—even a prison cell.

Deanne Wilson can testify to this. Last month, she ventured across the country to tie the knot with Alberto in a prison chapel. Standing beside each other, the straight-laced sales manager traded vows with the convicted murderer and the two bound themselves to eternal faithfulness.

Back home, Wilson imparted some advice at her postnuptial bachelorette party.

“I told all my girlfriends [who are] struggling on the dating scene to get a prison pen pal—to just try it out” she says. “There’s a lot of fish in the sea, but hell, there are a lot of fish behind bars too.”

Asterisks (*) indicate an inmate’s name has been changed to protect his privacy.

Illustrations by J. Longo | Images of prisoner letters and profiles courtesy of