Here’s What it’s Like Navigating Love After Lockup and in the Midst of Being Behind Bars
by Ashley Cobb



March 22, 2021


8 Minute Read


Here’s What it’s Like Navigating Love After Lockup and in the Midst of Being Behind Bars

Man in prison (Courtesy of Canva.com)
Courtesy of Canva.com

For the past few weeks, many have binge watched the hit show Love After Lockup, a show about finding love after incarceration. Episode after episode, I became fascinated with learning more about prison relationships. How does one find love while incarcerated? 

My curiosity led me to a website that I found on Facebook — a prison pen pal program. A study by Warwick University in 2015 found that these programs were “likely to raise prisoners’ chances of rehabilitation… through providing someone who accepts them as more than just ‘an offender’ and shows belief in their capacity for change.” Inmate.com allows incarcerated people to communicate through handwritten letters or emails with people in the outside world. 

Each person has a profile, much like a dating site, that describes their intentions, hopes and dreams once released. The profiles also contain information about their conviction, time served and date of release. After reading several profiles, one profile in particular, caught my attention–Leonard Love. Leonard is a handsome man and described himself to be 6’4, 260 lbs, charismatic, open-minded, and a visionary. His profile was very well written and discussed his life goals and accomplishments. However, Leonard is serving a 20-year sentence for bank robbery but has made tremendous strides to rehabilitate himself while incarcerated. He currently has a blog, where he talks about life in prison.

Out of sheer curiosity, I posted Leonard’s picture and profile on my Facebook page with the caption, “He has a better dating profile than folks on Tinder” and the responses were quite surprising. Leonard’s post received over 100 comments and 200 shares. I was shocked that women were willing to risk it all over a person they knew nothing about, outside of him being in prison. Oftentimes while watching Love After Lockup I would wonder what kind of person looks to prison pen pal websites to find a relationship? Interestingly enough, I now had my answer — everyday women, women that I know personally, women with degrees and careers — that’s who. 

He was extremely open to speak of his experience of looking for love during and after his sentence.

How has your dating life been while incarcerated? How many women do you date at one time? And how do you meet them?

Leonard Love
Leonard Love

My dating life has been fun, wild, and very interesting. I was once engaged to a millionaire, dated a 400-lb. woman, a doctor, an R&B singer and have had thousands of different women email, text or write me over the course of my 19 years of incarceration. In the beginning years of being on prison dating sites I dated 4 women at once but they all knew about each other as there is no reason to lie.

Once your sentence is completed, what will dating look like for you? 

As far as me looking to date once I’m released, I would say ‘yes’ as long as I could find a woman that is open-minded and could respect me as a man. One that wants to get to know me and know my heart. I won’t have much to give, but I am a priceless man in the sense that I know my worth and my purpose.

What type of women attract you to want to date them?

The type of women I normally date are very pretty (in my opinion), feminine, smart, have goals and dreams, work and enjoy life. The type I have mostly met while incarcerated have been single mothers, women that have problems with men in their lives. and women already in relationships but not happy and looking for some male companionship.

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Because you’ve been in prison for 20 years, do you think it’s best for you to sow your wild oats or are you looking to jump into a committed relationship?

It’s never ok to sleep around and want to have sex with multiple people. Yes, I have been gone 20 years yet I keep up with what is going on in the world and they have too many diseases and I  just need ONE woman and I will be fine.

Is there a certain kind of person you’re looking for upon the conclusion of your sentence?

I am looking for a woman that is well-rounded. Meaning she has her stuff together. I am not a man that thinks all women need to be barefoot and pregnant, or they cant have higher paying jobs than a man. It’s 2021 and women are smarter, more determined, and are not sitting back and waiting for a man to take care of them. I want a go-getter type of woman.

You don’t have any kids, are you looking to have kids once released?

I don’t have children due to the fact that I was very immature when I was younger, and I have been incarcerated since I was 25 years old. At this present moment I don’t want children due to the fact I need to get my life in order and then who knows.

Why do you think women reach out to you knowing you are in prison?

Well, a lot of women have reached out to me due to the fact they think I’m attractive, I have my head on straight, I don’t smoke or drink and I have accomplished many positive things being incarcerated. Also a lot of women like how I give back by mentoring the youth and at-risk teens so they don’t follow in the same footsteps as I did. Also I’m a nice guy!

When choosing to connect with someone while they’re incarcerated, it’s important to note that many are looking for companionship, while others may be on the chase for someone to put money on their books. It’s imperative to lean into discernment as a safeguard to protecting yourself from being taken advantage of in any way.