Love Behind Bars: Dating, Heartbreak, and Hope While Serving a 50-Year Sentence

Dawan Ingram explains why love behind bars is complicated, fragile, and often fleeting—but for those serving long sentences, it’s also a powerful reminder of what it means to feel human.

I’ve been incarcerated for the last 12 years. Many women have come and gone. Although each woman takes a piece of my heart with them, the heartaches don’t hurt like they used to. Every connection I make is a newfound excitement, but like food, I know eventually it will expire.

I am a prisoner. However, I am and always will be a human being, like everyone else, who wants genuine love. Am I naive to believe that it can be found while serving a 50-year sentence? Maybe.

The reality is, I have found love behind bars. The problem is trying to maintain love with so many obstacles, including the archenemy of humanity: time!

Prison Pen Pal Sites: From Scams to Genuine Love Behind Bars

There are hundreds of websites that claim to connect prisoners to women in the “free world.” Many of the websites available will take a prisoner’s money. In some cases, they actually post a profile, but in the worst cases, they are scams. There are some very successful websites such as Write A Prisoner that actually fulfill their promise of making connections. I personally subscribed to the site, and I know several others who have as well, with great experiences.

I have met some crazy women. A girl once told me if I didn’t come home and be with her, she would kill me. Actually, I have been threatened quite a few times. I assure you, the threats did not deter me. However, I did run for the fences.

I have had women tell me that they loved me and that they would always be around to support my fight for freedom. Then they disappeared after some time. The longest relationship lasted five years, and when it ended it was the hardest.

I met the woman who I’ll call Ro through a mutual friend. I’ve known him since I was 14 years old. He told me that she was loyal and a good girl. Her problem was the men she decided to date were the exact opposite. My friend told us both about each other, and I was interested, so I asked for her number. I kept asking, “Is she sexy?” and he kept saying, “I don’t look at her like that.”

When Ro and I spoke on the phone, everything flowed naturally, and we began talking every day. She became a little possessive, but I though it was cute because I felt the same way about her. She first came to see me when I was in the Essex County Correctional Facility. The moment I saw her I could not stop smiling. She was beautiful.

She supported me throughout the entire trial process. She came to my court dates, spoke with my lawyers, and even wrote letters to the judge. Understandably, when I lost trial, she was devastated. She had a nervous breakdown and fell into a depression. After I was sentenced and sent to prison, things became a lot better, but not for long. The contact visits were the best part of being in prison. In the county jail, only window visits are allowed.

I learned so much about her, and I believed she truly wanted things to work out. She came to visit me often. She sent money, pictures, and did everything a prisoner could want. She was special! As time passed by and I lost a few appeals, she became discouraged. She was 14 years older than me but actually looked younger. She was beautiful! The lonely trips and empty bed had taken a toll on things, and once she found gray hairs, she panicked.

One day, I called, and immediately she began crying like never before. I knew in my heart it was over. The circumstances were breaking her down, and reluctantly I had to accept it and just let her go.

Am I selfish for taking time out of her life, not knowing exactly if or when I will go home? I don’t know the answer to the question, but sometimes I feel guilty. I am proud to say that I was honest about the crime I’m accused of, as well as my sentence. I know numerous prisoners who lie to women to keep them around, and it always ends badly.

Learning to Cherish Fleeting Love and Let Go Behind Bars

The revolving door has made me accept that all women I meet while I’m in prison have an expiration date. Eventually, they all will leave. Ive learned to enjoy the moments as they come. I take what I can get, but most importantly I give a piece of me that will without a doubt be remembered forever.

One thing that I’ve noticed, all the women I’ve met while in prison were searching for the same thing: genuine love. A man who listened and was attentive, sent them gifts randomly, taught them new things, made them laugh, and supported their visions. The hardest part was not having me there, is what I was told over and over again. Hearing those words still haunt me!

I never hold a grudge or any malice in my heart when a woman decides to move on. I was often asked by different women, “If I was locked up and you were free, would you wait for me?” I really thought long and hard about that question, and the most honest answer I came up with was, I don’t know.

The more I ponder my experiences, I accept my situation. The heartaches hurt less after parting ways with a woman I vibed with. Overall, I’m grateful for the women I’ve met and the women I will meet. Im only 29. Who knows what the future has in store? Maybe I will find the one woman who doesn’t have an expiration date.

Yesterday is history. Tomorrow is a mystery. And love behind bars hurts.

Enjoy this story? Check out Aging in Prison When You’re Innocent

The post Love Behind Bars: Dating, Heartbreak, and Hope While Serving a 50-Year Sentence first appeared on Prison Writers.