These Women Seek Out Romantic Relationships with Incarcerated Men

In this fascinating work, Isenberg collects the results of extensive interviews with women who seek relationships with convicted killers, as well as conversations with psychiatrists, social workers, and prison officials. Her research reveals how of these women know exactly what they are getting into—yet they are willing to risk it all.

This updated edition of Women Who Love Men Who Kill includes gripping new case studies, providing an absorbing look at how the digital age is revolutionizing this unusual phenomenon. Meet the young women writing “fan fiction” featuring America’s most sadistic murderers; the killer serving consecutive life sentences for strangling his wife and smothering his toddler daughters—and the women who visit him in prison; the high-powered journalist who fell in love and risked it all for “Pharma Bro” Martin Shkreli; and many other women absorbed in online and real-life dalliances with their killer men.

The “engrossing, thoroughly researched look at women who are in romantic relationships with incarcerated men”—fully updated with twenty-first-century cases (Publishers Weekly).

How Women On The Outside Meet Prisoners

All over America and internationally, women go online looking for dates, romance, love, and marriage. Most choose Bumble or Tinder. But a few select one of many meet-a-prisoner websites, where lonely and determined prisoners pay small fees to place their bios and photos online, hoping to gain a pen pal or a girlfriend, and thus admittance to the outside world.

Why would a woman choose such a website over a more conventional dating service? It’s a question asked as often as “Why do women love men who kill?” Why prison romance? Why seek out men behind bars? Are these women crazy?

I answered this question in the first edition of Women Who Love Men Who Kill by developing theories based ondozens of interviews with these women. Now, in the age ofthe internet, the reasons are the same—but with someslight differences.

The women interviewed in the twenty-first century often answered “boredom” as a simple reason for scrolling down a prisoner pen pal site. Sometimes, further investigation reveals a past history of abuse: She is seeking safety in a relationship with a man behind bars, who can’t hurt her but can only love her.

Or perhaps she was looking for something to do during the COVID-19 pandemic and came across writeaprisoner.com. But is that likely? Maybe she was trying to find a man who she could sort of control because he was caged.

Ann Dayton*, a thirty-year-old single mother, is a serial scroller on writeaprisoner.com, the most popular site for women looking to meet inmates. Ann has been involved with several men, including the father of her three-year-old daughter. She explained her attraction to the activity and men behind bars.

“All the men have to do is concentrate on one thing—you—and they put all the effort into one thing: your relationship. They don’t have anybody else to talk to. All they do is talk about a family life and what they’re gonna do when they come home,” Ann said, adding that she likes the attention.

Ann had one or two early inmate correspondents, then became seriously involved with a third, Daniel Valerian,* doing time in maximum security at Warren Correctional Facility in Ohio for nine counts of first- and second-degree home invasion. They first communicated via email and phone during the last year of his nine-year sentence. Ann was thrilled with Daniel—while he was inside. She recalls, 

"I remembered how happy I was. Like, I still have all my stuff that I wanted to do with my family and live my life. But I still felt loved, and I still had the moral support of somebody there to talk to every day . . ."

[He] never asked me for money . . . I didn’t have to do anything I didn’t want to, except for load money on the phone. And even then, he would have his brother send me money sometimes to help me out with that.

If she needed money for gas to drive to see him (she lived in Terre Haute, Indiana, 200 miles from the prison), his brother would send her $80.

The couple’s meeting on writeaprisoner.com is common, said the website’s founder and president, Adam Lovell, adding that many, many couples “get together” on his website. As of February 6, 2021, the site lists 30,000 inmates, who are 90 percent men, 9 percent women, and 1 percent “other.” A prisoner pays a yearly fee of $50 for an online ad of 250 words or less plus a photo. Lovell requires prisoners to list their crimes, and each prisoner’s ad is linked to his particular state’s department of corrections.

Before Daniel, Ann had “a bad person” as a boyfriend. Then she dated someone else who was “into drugs,” with whom she had physical fights. She experienced “mental abuse, with him trying to get me out of the house so he could cheat on me. He would always lie. Make me feel like I was nuts.”

Ann’s childhood story was not much better; early puberty led her into unusually early sexual development and activity. “I was way too young. Eleven. I wanted a relationship.” At that young age, she had a seventeen-yearold boyfriend who initiated her into sex; after that, “I became boy crazy.” Strangely, she said, her father did not object: “He is cool, calm, collected. ‘Whatever makes you happy.’”

Young years struggling with sexual identity and several “bad” boyfriends led Ann to seek safety with a man behind bars. She fell in love with Daniel, but the parameters of a prison online romance meant she didn’t really know him. He was at the end of his nine-year sentence, and within months of their first correspondence—via JPay and GTL, companies that run internet services for prisoners—Ann and Daniel were living together and she was pregnant.

Fast forward: he cheated, lied, and then tried to gaslight her. But she finally left him, and now she’s a single mother trying to get her life in order. Succeeding, too: “I go to the gym. I do yoga. I work on myself.” Ann says she will not be scrolling through the numerous prison pen pal websites anytime soon; she’s done with prisoners.

Women who go on these sites often mention looking for something different. Boredom can be alleviated this way, they think, so they “go online and look for new pictures of lonely prisoners.” The number of prison romances are not recorded, although marriages and conjugal visits are tracked by most states.

Unofficially (of course), those in the criminal justice system acknowledge that these relationships exist; they’re more common than the public knows. And the more heinous a crime, the longer a sentence, the more notorious the criminal—the more appealing the particular inmate will be for women on the outside.

Before the internet, romances originated between women and prisoners who spent time in all kinds of penal institutions. But these relationships are small in number today compared to those that begin on pen pal websites. The internet has revolutionized prison dating so that any woman anywhere can contact a prisoner through his online ad.

There are no geographical boundaries: A woman in England can marry a convict in Texas and a woman in Australia can fall for an inmate in Kansas. International relationships are common but go only one way; women outside the U.S. find men behind American bars, since there are so many of them. The only barrier is language, which is easily overcome—the women and the prisoners speak the universal language of love. Or what they believe is love.

There is an element of fantasy in both the ads prisoners put online and the responses they receive from women. The men send photos and are honest about their crimes, but their interests often read as if they’re on a college campus or hiking in the woods. One man in a maximum correctional prison in upstate New York writes in his ad that he “loves people, dogs, hunting and fishing, and politics.”

But he is serving a life sentence for ordering the murder of an eight-year-old boy and his mother, so he will likely never hunt or fish or vote again. Nevertheless, he is optimistic that the internet will change his life, that he’ll meet someone and fall in love.

Another inmate posts that he is upset that prisoners are seen as cold and emotionless, or as savages. This is not true for him; he is warm and caring, as human as the next guy— even though he’s a convicted killer. He is hoping that some woman will realize that he isn’t a beast and answer his ad. After six months, he heard from a woman he liked instantly. He plied her with poetry and long love letters, and they now have a romance which has boosted her self-esteem and also improved his image with both guards and fellow prisoners.

According to Adam Lovell, the prisoners who take the time and make the effort to post ads are those who are optimistic. Those who don’t bother are institutionalized, hopeless, needing prison life’s restrictions and routines. When one such prisoner committed an infraction only hours before his scheduled release, he explained he wanted to be rearrested and reconvicted in order to remain in prison: “I got nowhere to go. This is my home. It’s warm here and they feed me,” Lovell recounted.

Of writeaprisoner.com’s 55,000 visitors a day, only a few hundred actually follow through, said Lovell. He noted that X-rated messages are not passed on, and that the men who receive the most responses are either the best looking, the youngest, or have the saddest stories. Death row inmates are popular, especially with women in the UK and Australia who oppose the death penalty. For long-running ads that get no response, churches sometimes intervene with volunteer pen pals. (And some of these volunteers end up romantically involved.)

Sometimes a random connection online can lead to lasting but impossible love. When Emma Fountain*, a masseuse from Sydney, Australia, was “fooling around” online one day, she Googled “prisoners and websites”—the first site to come up was writeaprisoner.com. “So I literally just went on the website, scrolled down and then just randomly stopped when the mouse stopped scrolling and decided to choose whoever it landed on. It landed on Manuel.”

Now, two years later, she believes she is deeply in love—although she is certain it’s a doomed relationship. Manuel Torres*, who committed murder as a young gang member, is imprisoned in Louisiana’s notorious maximum-security prison, Angola; Emma lives thousands of miles away at a time when international travel is difficult, if not impossible. They communicate via email for the most part.

Their attraction is surprising, until Emma details the connection:

“The way he explained his life, there was a recurring theme throughout that made me feel like I really related to him. We were both abandoned as kids, though I wasn’t abandoned the same way he was. His was physical. With me, I wasn’t understood. My mom would just leave me to it. She didn’t think that giving me affection was the right thing . . . [Manuel and I] were both very confused and had to grow up very quickly.”

After agreeing they had never felt this way before, Manuel and Emma declared their love for each other. They are content to share their deep, emotional connection long distance for now, and perhaps forever.

Emma explains the intense closeness they feel:

“We both struggled to understand other people. We both didn’t have a purpose in life. He explained that he has never felt like he had a meaning for being alive and he was just existing. I felt the same. I’ve never really understood why I’m here. I’ve always assumed that I probably wouldn’t live past the age of forty because I just don’t see a purpose for being here. I couldn’t believe someone else felt the same way.”

Her past includes an abusive father, a neglectful mother, and a fiancé who cheated on her then lied about it. And Manuel has mental health issues exacerbated by prison—he has even attempted suicide. Emma expresses despair: “You know what it would do to me if he did commit suicide? There’s not a chance that I would be here right now. If I got that phone call saying that he had gone, I’m gone too. We are very, very set on each other. There is no way I could live without him,” she says.

Manuel has twelve more years at Angola. And Emma is 8,700 miles away.

Featured photo: Denis Oliveira / Unsplash