Dating Again

Parts of your story hit my soul because of the similarities, mainly dealing with an incarcerated man. Like you, I did not have a happy ending. Long story short, the trauma took its toll. I’m sure you know what I mean. I was devastated. My family and friends did their best to be supportive but they could not understand. I’ve done therapy and continue in my healing journey. My questions for you are how do you date with an open mind after dealing with someone who was incarcerated? Would you date an incarcerated man again?


First let me say that I didn’t start dating right away. It was probably three years after we broke up before I went on my first date. I was still healing and wasn’t really interested in dating. I hated the idea of starting over again, having to get to know someone new. I think that kept me from being open in the beginning. Once I started actively dating, I struggled to find balance between my usual open, loving self and my now wiser self who’d learned some hard lessons about love. I’m a hopeless romantic and still believe in the power of #blacklove, but I was guarded.

I knew I had to be vulnerable to find love again, but I was afraid of what that vulnerability might bring. What if I opened up to a guy, trying to learn each other, and he took my kindness for weakness or turned the things I said in vulnerable moments against me? I had thrown caution to the wind with Shaka but my head and my heart wouldn’t let me do that again.

I didn’t realize where my pain points were—where I still needed healing—until I started dating a guy I really liked. Trust was an issue for me—trusting him and trusting myself. Early on, I questioned whether he was who he said he was. I didn’t trust those gut feelings, the same ones I was so sure about when I met Shaka. I kept looking for signs that he was fronting. It was hard, but I had to quiet the fears I had. The fear of being wrong, again. The fear of being hurt. I had to replace those thoughts with affirmations. You are worthy. And I checked in with myself often—is this feeling rooted in an old wound? I also had to remind myself to be in the moment and take the pressure off of him and me to be a certain way. Being tuned into a higher power helped me when I started overthinking.

I recommend you listen to your heart. If you’re not ready to date, wait. Do the work that’s needed to heal your broken heart and trust again. If you’re ready, be patient with yourself. Use this time to figure out what you like and what you don’t like. Learn your triggers. Tune into yourself so you know when your guard is up or past trauma is showing up, so you can work through it. When it gets tough, just trust that God has more for you. More love. More joy. Sometimes we have to get out of our own way.

To answer your second question, I learned a lot from my experience and have no regrets, but I wouldn’t make that choice again.

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