From the end of 2021 to November of 2022, I was in a relationship with an ex-convict. While I know that sounds crazy, he told me he was wrongfully convicted. Despite his innocence, he spent 15 years in prison. And the cherry on top of it all was I knew all of this before deciding to enter a relationship with him. I wanted to write my story in order to share what I learned from dating an ex-con.
When I first found out he spent 15 years in prison, my stomach dropped. My first thought was how hard it must be for him to adjust to society after spending so long locked away. I also started worrying about what or who happened to him while in prison. And then the thought of he hasn’t had the same life experiences that I have had came to me. But what I didn’t expect was how this would play out in our relationship.
The first few weeks were like the honeymoon phase. I couldn’t get enough of him. I was trying to see him every other day when I was off work and kid-free, and spending the entire weekend with him on my kid-free weekends. We would text often along with plenty of video and phone calls. Honestly, I thought I won the lottery. And despite his past, he was a successful professor about to get his Master’s in theology. The man spent Sundays preaching as a guest preacher at churches as well as grading and lesson planning. It didn’t even seem like he spent any time in prison.
Then things started to shift. First, he started comparing me to the person he created in his mind from reading this blog. Then he started comparing the first few weeks to the current time we were in. See, he didn’t have a car (yet), so I was the one driving to him 3 out of the 4 weekends in a month. Then, on the 4th weekend, he would complain about the long train ride he had to take to see me. I found it a little annoying but I continued to do my part and push on since I was starting to really like him.
Then in April, he got a car and broke up with me over text message while I was at work. He blindsided me, and I ended up crying in the staff lunchroom at work. I told him to send me the ticket to my graduation back in the mail. Hours later, he was calling and begging to let me talk to him in person. He came over, despite me not wanting him to since I had Aria. So, he met Aria and then explained to me how he took some bad advice from his ex. She had told him to break up to see if I would fight for the relationship. Since I didn’t “fight” the plan backfired and he regretted his decisions. Also, why he didn’t just talk to me rather than asking an ex for advice flabbergasted me. Unfortunately, this was just the beginning of our demise.
I can’t explain to you why I gave him another chance after the text message breakup. The only explanation I have is that I had fallen in love with him. And with the thought of our future together. And this wasn’t the only time we broke up. As time went on, he became harder to communicate with. Our phone conversations became very one-sided. It felt like I had to carry every conversation. He wouldn’t tell me much, and often it felt like I was trying to pry information out of him. As I became more vulnerable, he became more clammed up. He started giving me unsolicited advice on my life, lifestyle, and career/education goals. He didn’t like how much I socialized with my friends. He didn’t like how I prioritized things in my life. And he didn’t like that he wasn’t my top priority.
Things started to fall apart once he claimed that he was doing all of the work in the relationship and I wasn’t nearly close to putting as much into it as him. He felt like he was doing most of the driving, kinda like how we started the relationship. And he was right. I felt like a nuisance to him. He would tell me that he felt he was doing everything right and as much as he could for the relationship, but that I just wasn’t. And then my marathon happened. He knew about it, and I had invited him to go with me. I even paid for a hotel room and took Southwest all in hopes that he would join me. But when the time came, he never even tried to go. When I got back, he finally told me that he had never wanted to go to cheer me on. He felt he had shown up enough in my life. But for me, it wasn’t enough.
So I broke up with him. I had high hopes that we could be friends, so I asked for him to give me time to process and heal. Time away from him. I told him I needed a break in communication. But unfortunately he couldn’t respect my wishes. He kept reaching out. First through text, then email, then Facebook messenger. I had to block him on every platform just for it to “stop.”
It’s unfortunate, but in hindsight I should’ve seen it coming. I should have thought more about how his time in prison affected not just his lack of social skills but also his ability to mature naturally. I think his career and educational successes lured me in. Then, when he bought a car and a condo, I really thought he had it all together. But when he didn’t trust me enough to hang out with my running friends, I started to see that he didn’t have it all together. When he didn’t respect me enough to listen to me and my wishes, I knew I wasn’t dealing with someone on the same level as me. My only regret is not leaving sooner.
I guess this is what I get for giving the underdog a chance. I’m wondering from my readers, have you ever dated an ex-con? And how did it go? Or would you? Am I crazy for even giving him a chance?
The many layers of Jen 