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Help! My boyfriend was in jail. Can I trust him?

One of my newest guilty pleasures is the VH1 reality show “Mob Wives.” The show follows a group of outrageous Staten Island women whose fathers, husbands and boyfriends are all currently or formerly incarcerated. One plot-line has the women trying to figure out whether they should continue to date shady prison characters. 

So you meet someone interesting, start dating and then he confesses to you that he has a prison record. Is this someone you can trust? Should you continue to date him? You are in the right place with your love advice question — and not a moment too soon. Have no fear, your Official Lifestyle Passionista is here.

Remember, women who are empowered know that they are worthy of being loved by honest and positive men. There are several questions that you should ask yourself if you are wondering whether to date a man who has been in jail ?

1. When did your dude commit the crime?

If your boyfriend is now 30 years old and he was a juvenile offender at age 15, you don’t want to necessarily hold this against him. Everyone has character blemishes. Keep your wits about you, get the facts and be open to hearing his story.

2. What was the crime that your potential boyfriend committed?

Did he jaywalk and talk back to a police officer, earning him a night in the slammer? Or did he go to jail after starting an arson fire in a rage? These are two drastically different situations. Find out what the crime was before rushing to judgment. A person who littered and a mass murderer are two different things.

However, if this person is a “bad boy” who is bent on causing trouble and living beyond the law, you have to ask yourself what you can live with. Anyone who acts out for the sake of acting out can put you in harm’s way often without meaning to. Rule number one is that you deserve to be happy.

3. How much time was served in prison?

Prison rarely rehabilitates anyone. Most people in jail only learn how to become better criminals. Again, there is a big difference between someone spending the night in prison and a hardened criminal who just came home from a five-year stint in the pokey. If it is the latter, I would probably advise you to run!

4. What does your man feel about this crime now?

Is your guy remorseful? Does he regret what happened? If he is still feel like things are everyone else’s fault, that is a bad sign. Evolved adults take responsibility for their lives and their actions.

5. Has your guy undergone therapy?

Anyone with a history of violence against women will continue with these issues in different forms unless receiving some sort of treatment. Again, prison alone should not be considered as a source of rehabilitation. Our prisons are largely about punishment, not redemption. It doesn’t matter what their history is. No one should ever humiliate or belittle you.

6. What is the legal fallout? Is he out on bail? Parole?

There are some cases where you should just run. While we want to believe in the best for everyone, not every person is able to be rehabilitated. If you have even the slightest bit of doubt, then it is time bid your prison lover a fond adieu.

Bonus.

Always run a full criminal background check no matter what they say. While our objective is not to judge, we want you to have a sense of security. You deserve to feel good in love and be safe in all ways — mentally, spiritually and physically.

As I always say, be good. And if you can’t be good, be safe.

Happy Dating!

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