Dating An Ex Criminal. My Boyfriend Was in Jail! Luv Em Or Leave Em Relationship Advice Series (VIDEO)

Should I Date A Criminal?

Passionista Principle: You have the right to be “picky” in all matters of love. Don’t let anyone tell you otherwise.

You meet a cutie and go out on a date. Somewhere between “You’re so funny” and “Please pass the potatoes,” he reveals that he has been in prison. Or you’ve been dating for a while and then your new love shares with you his secret past or current life on parole. Yikes! Your boyfriend is cute, smart, fun and a jailbird. So what should you do? Is he “winning?”

This is an important question because prisons in our current prison industrial complex are not centered around rehabilitation. Jail in America is big business. The United Stated has the highest number of people in the population incarcerated. And as we know, some populations are jailed more often than others. Crimes are unevenly enforced in urban communities. I have sadly had family members in prison. So what do you do when you find out that your crush was a criminal?


File this under Phaedra Parks on The Real Housewives of Atlanta whose husband Apollo was in jail. Would you marry someone who has been incarcerated? Although I consider my blog and web series to be a judgment free zone the hard truth is that I am unfortunately not as open minded as I hope to be one day. I say that it all comes down to questions.


QUESTIONS TO ASK YOURSELF: What was the crime that your boyfriend committed? A violent crime? A white collar crime? How old was he when he went to jail? What has he done to rehabilitate himself? Has he had therapy since he came home from prison?

IF YOUR MAN HAS A CRIMINAL PAST…
  • 1. Always run a background check to get information for you. 
  • 2. I have to say for the record that if this person has committed a violent crime, RUN. 
  • 3. Like Oprah Winfrey always says when she quotes Dr. Maya Angelou, “when someone tells you who they are, believe, them.”

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