He’s served time—should you serve him his walking papers?

Dilemma

I recently met someone who told me that they had served some time in a correctional facility. Me being a person not to judge and believing in second chances chose to go out with this person, but I feel like his lockdown has took a toll on him. When we met, he was working as a mechanic but on work release. I’ve visited him but seen the red flags. Should I give him the benefit of the doubt? He gets out in March.

Deconstruction

This is definitely a tough one, as your heart is pulling you in one direction, while your head pulls in another. First of all, let me commend you for your Christian compassion, non-judgmental attitude, and your openness to forgiveness and second chances. All of these are wonderful traits to possess, especially for someone who identifies him or herself as a Christian. However, sadly, sometimes the most kind and compassionate people are the ones who get taken advantage of by those with manipulative motives; they feel they can easily prey on your openness and willingness to forgive. This doesn’t mean you should stop being kind and compassionate, just that you should practice self-preserving kindness—which I will get to in a moment.

Before that, a couple key considerations regarding your situation: First of all, you did not mention why he served time. Was it a violent crime (i.e. domestic violence or some sort of battery charge)? If that is the case, read no further. Disengage yourself from this man immediately. Sure, maybe he has changed, but with the risk being your physical safety, there is no room for chances. And besides, you are a person who deserves better than that. My second question is what are the red flags you mention that you have witnessed? Again, if they are any of those on Nicholle’s list (see “Mr. Perfect Did What? Ignore These Red Flags at Your Own Risk,” November 2007), again, you can wish him all the happiness and healing in the world, while you go find yourself someone who will really make you happy—because this man won’t.

However, let’s consider for a moment that he was not imprisoned for a violent crime and that you do see positive traits and have experienced respectful treatment from this man. (Which, incidentally, is not the vibe I get from your question; however, let’s indulge this possibility for a moment.) My question then becomes this: What have you witnessed him DOING to make a change in his life? The reason for the emphasis on “doing” is that talking about changing or promising to change is not enough; actions are the proof you are looking for. Is he responsible at his job? Is he honest about his past mistakes and actively making amends? Is he practicing his faith and behaving in a Christian manner? Has he gotten clean and sober (if that was an issue)? Most importantly, does he treat you with the kindness and respect you are showing him by giving him a chance?

If you can honestly say that he meets these criteria, and if you really feel there is a special connection, you can be casual friends with this man. Do not make him a priority in your life, and do not promise him any relationship upon his release. After he gets out in March, give him about six months, and see what he does with his life. After that point, if he truly has made significant changes and you see no red flags, proceed with extreme CAUTION. Remember, he is already on his “second chance.” One wrong move—with love or the law—and he’s out.

So now back to what I refer to as self-preserving kindness. This is the term I use to describe when you approach someone with a kind and open heart, as a fellow human being and Christian, yet still put your own wellbeing first. While everyone has their own specific beliefs, my feeling is that God would not be opposed to us acting in our own best interests when it is to protect our wellbeing or safeguard our faith. We are not talking here about “being out for yourself” in terms of financial gain or some other material advancement; we are talking about protecting your welfare . . . which in this case, may mean moving on to a man without such a questionable past.

Until next time, never lose faith . . . it only takes a moment to meet your soul mate.

Regina