Why Did a Nice Girl Like Me Date a Guy in Jail?

What women really think about news, politics, and culture.
May 16 2013 6:45 AM

Love Behind Bars

Why did a nice girl like me date an inmate?

Illustration by Robert Neubecker.

Illustration by Robert Neubecker.

“I love you.” They were words I had longed to hear from Justin for years, but when he finally spoke them, something held me back. Three layers of Plexiglass and armed guards, to be precise.

Justin and I had dated off and on for years, and some part of me always believed we would end up married. Our parents were close friends, and we’d grown up together. He had always been a troublemaker. In fact, that might be what drew me to him. I was quiet, studious, painfully shy; he was full of boisterous energy and crude jokes. I loved his pug nose, his fiery red hair, and his teasing smiles. But as his school detentions led to expulsions and, eventually, arrests for possession of weed and then burglaries, we fell out of touch. I was ambitious, and my sights were set on anywhere but Delaware. I couldn’t afford to have Justin drag me down. Maybe when got his act together, I told myself, we could finally have a real relationship.

But in the spring of 2006, Justin came back into my life with a phone call from my mother. This time, he’d really screwed up, my mom told me; he’d been arrested as an accomplice in a double murder. His friend, a prescription drug addict, snapped one night and shot two of his dealers. Justin said his friend turned the gun on him and demanded that he help bury the bodies; Justin was, in turn, arrested and imprisoned.


I had pushed myself to get through my final year at Georgetown. For various reasons I felt utterly disconnected from my family and friends back home, who were struggling with their own problems. But I couldn’t quite find a way to fit in at school either, where one relationship after another imploded. I felt lost and lonely. I drank too much, drove too fast, worked too hard, and dated men even worse off emotionally than me.

The summer after I graduated from college in 2007, I moved back to Delaware and drifted along the couches and floors of family and friends. I was the girl who had always known what she wanted, the girl who was finally going to make her family proud, but I felt my drive and ambition draining away. I no longer had to push myself to maintain a full-time job and a decent GPA and good social standing, so I swung to the other extreme. I stayed up late writing or reading or just thinking, and slept in until I felt like getting up. I dyed my hair green and I cursed in front of children and I showed up late for work at Subway. For the first time, I allowed myself to admit I had no idea what I was doing.

That’s when Justin’s letters began finding me with increasing regularity. In the months before the trial, Justin had a lot of time to think. And he often thought of me. We wrote about books and family and mutual friends. I’d tell him about quitting Subway after only a few weeks, and then I’d describe my nights working at the next job, front desk clerk at a hotel and casino. He’d describe a fight he’d witnessed and poker games with his new cellmate. Time wore on, and the letters became more intimate. I told him about my disastrous dating experiences in college: the boyfriend who cheated on me with my roommate; the supervisor at work who was sleeping with me and a handful of other co-workers; the older guy who was living in a Neverland of no commitment. The physical boundaries between me and Justin only served to release us from our inhibitions; nothing was off limits. Writing to him freed me. After all, who was he to judge?

Our interactions were carefully circumscribed by guards and glass and distance. After a few months, we were talking on the phone in daily 15-minute bursts, and we wrote letters to each other every day. Every other week, we greeted each other shyly between panes of smudged glass.

Between my family problems and my painful dating history, I wasn’t ready for a real relationship. I loved him, but I also cherished the convenience the physical distance provided. If I needed space, Justin didn’t exist to me. It was as easy as not answering a phone call or not picking up the letter lying on the counter. But when I did need him, I could conjure him up with a pen and paper.

He was kind and sensitive in his letters, and I was fun and flirtatious in mine. On paper, he could be the man that I longed for, and that he longed to be. I never really had to figure out how he would treat me after a bad day at work, or whether we would fight over money or our in-laws. How much can you ever really know about another person, anyway?

Prison relationships, in particular, “tend to be built mostly on fantasy of the other,” Harley Conner assures me. Conner is a doctoral candidate in clinical psychology at George Washington University who has worked as a probation counselor to jailed youth and has conducted clinical work in forensic and correctional settings for about three years. A pen pal can project all of her hopes and dreams on an inmate who wants nothing more than to be a repository of those desires, Conner explains.