Who we fall for romantically is often something we can’t control. That’s why some of us end up with a plumber even if we’re a doctor. That’s why some of us marry Christians even if we were raised in a strict Jewish household. And that’s why some of us fall for people with a criminal past even if we’re law abiding citizens. Dating someone who has been is prison brings to the table its own special considerations and challenges.
Analyze how you feel about the relationship
Once you find out that the person to whom you’re attracted has been in prison, you need to ask yourself if you can really see yourself in a relationship with that person. It’s helpful to know why the person was incarcerated. Were there special circumstances? Was the person a white collar criminal? A thief? A drug dealer? A violent offender? Does the nature of the crime of which the person was convicted make a difference to you?
How comfortable are you with an ex-con?
Another thing to ask yourself is if you feel comfortable and safe with this person. If the person’s conviction was related to a psychological or psychiatric issue, has he or she sought treatment? If the incarceration was related to addiction, does the person regularly attend meetings like Alcoholics or Narcotics Anonymous? Does your potential paramour exhibit other indications of being committed to succeeding in society now, like holding down a regular job and maintaining a home?
Getting over the past
If the former prisoner shows all the signs of rehabilitation and being a productive member of society, then the question becomes how you’re going to deal with the person’s past. There’s certainly a stigma in our society to people who have been imprisoned, and that stigma will extend to you as someone who chooses to pursue a romantic relationship with the person. Are you prepared for the fact that others will judge you based on the company you keep?
Don’t expect too much discussion about prison
You’ll also need to be prepared to talk openly and honestly about the person’s prison past without expecting the person to share too much. Spending time in the penal system is neither pleasant nor easy, and people who have been there typically don’t have a lot of fond memories. Don’t pressure the person to talk about life on the inside, as for many it is a traumatic and painful experience. You’ve likely seen movies and television shows depicting prison life, so you know that it’s not all sunshine and roses. And besides, if your boyfriend or girlfriend just spent the last few years living a life like an extra from Oz or Prison Break, do you really want the nitty-gritty details?
Thinking clearly about the situation
The knowledge you have about a felon’s past is for reference, not residence; that is, take that information and use it as a guide, but don’t get hung up on it to the point that you can’t live comfortably. You’ll want to make it clear from the very beginning that you won’t tolerate any sort of behavior that jeopardizes your life, livelihood, or relationship. Then again, if you’re constantly worried about getting pulled over for not wearing a seat belt, then dating a con is probably not for you.Note: If you’re looking specifically for a relationship with a person in the prison system, there are many online matchmaking websites available that cater to this preference.
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