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Beyond Bars: Navigating the dating scene after being in prison

By Brian Wood, Beyond Bars Columnist - | Sep 17, 2018

Part of one’s acclimation from prison to the outside world is going from the constant interaction with other people, where it’s impossible to get time alone, to perhaps a situation where alone is the norm. And in my life before going to prison, there really hadn’t been another time where I couldn’t identify someone I was really close to. I’ve always had that best friend, a significant other, or even that partner in crime – literally.

I imagine loneliness is something many parolees deal with as they enter the real world. The biggest pitfall I’ve heard for parolees is hooking up with “old friends.” I heard two stories just this week that ended with “old friends” and then a drug overdose. R.I.P. Jimmy and Ben.

I’ve also seen parolees combating the loneliness by jumping right into a relationship, which is rarely a positive thing. With that in mind, and because I got out a year early, I told myself I would not date for the first year. It sounds reasonable when I say it, but the practical application requires some discipline. For the most part, I feel largely unfit to date, so it hasn’t been too difficult.

When I first got out, I had a friend tell me her friend thought I was cute and was asking about me. I asked if her friend knew I just got out of prison and she told me no. I suggested she tell her friend about that first. So, she got back to me and told me the girl was still interested even after learning I was on parole and lived with my parents. I decided that was a red flag. She is probably super open-minded and a great person, but that was a deal breaker for me at the time.

As I’ve spent some more time out, I’ve since relaxed my stance, or in other words, I haven’t been able to stay disciplined and completely stick to the plan. This same friend convinced me to try one of those dating apps. About halfway through my first online date experience, I dropped the prison bomb. She was nice about it, but like overly nice.

If the first half of the date was like I was being evaluated by a professional baseball scout as I played, then the second half was like I was being encouraged by my mother in a little league game after I had just struck out.

After that experience, I decided I’d throw the prison thing right up on my profile. It read: I’m only 5’9″, so tall, dark and handsome need not apply. Sorry, it’s not you, it’s me. Also, I just got out of prison six months ago, on the plus side, you know all my photos are current.

With all that out in the open, I set up another date. I was on the phone with a girl as I drove to meet her and made a comment about not being familiar with all the new stuff out here because I had been gone for so long. She processed and then stated she thought I had been joking about the prison thing… She quickly changed her mind about meeting me, but was at least nice enough to text me she wasn’t coming. I told her I understood. I deleted the dating app shortly thereafter.

This is part of my reality now. There are many people who will never be OK with dating an ex-con and that’s OK. When I was in prison, many prisoners who had been released and were back claimed being fresh out of prison makes you a chick magnet. I was skeptical and rightfully so, as that has been the opposite of my experience.


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