Eight years ago, I was driving an Acura TL on my way to a chop shop. I had recently lifted the luxury whip from a suburb, and I was thinking about the $2,000 I would fetch for the new wheels. An unmarked police car pulled up alongside me at a stoplight. Two officers leaped out with their weapons drawn. Suddenly, my joyride was over.

That was the last time I was arrested, but it wasn’t the first. Growing up in Long Branch, New Jersey, I began running with a small teenage crew as a petty thief. By the time I was 20, my modus operandi was grand theft auto and identity theft. In 1992 I was sentenced to three and a half years at the Albert C. Wagner Youth Correctional Facility for those crimes.

It’s hard for me to believe I did all those crazy things. I was raised in a working-class, Christian family. But whenever getting paid the right way wasn’t easy, I turned to the streets to get money. After getting locked up a second time, I decided to get my life together. Today I’m a college graduate and I work full-time as an editor at a prominent men’s magazine. I respect the law at all times. I was raised by my mother and older sister, so my love and reverence for Black women is virtually unconditional. I can say with confidence that I’m a great catch for any woman.

That’s not to say my experiences with dating and relationships have been a cakewalk. The hardest part of getting to know a woman is always when and how to inform her about my past. I tend to go for ladies with middle-class backgrounds and professional occupations. I always consider whether a woman and I will become serious before getting all confessional. I ask myself, Can she handle the truth?

I tell my significant other about my past after two to four months of dating. I like to show her the good guy I am now first. So far, I haven’t had a woman immediately stop seeing me.

Maybe ladies think it’s the best of both worlds to date a professional man with a bad-boy edge. But that novelty and initial acceptance can fade. One woman said she was fine with my past, but then reminded me she would “never write or visit a man in prison.” Another woman would get suspicious if I suddenly had extra money.

Their apprehension makes me second-guess being open, but nondisclosure is not an option. I once told my girlfriend of four months about my crimes. This was just two months before I was sent to prison the last time. My criminal ways and my hesitation to tell her the truth cost me the love of my life.

I can’t advise women how to proceed in relationships with formerly incarcerated men. But if you’re wondering whether he will reoffend, pay attention to the friends he keeps and the type of life he’s leading. Try to evaluate his present character and don’t harp on the past.

Joel Randell is currently finishing his memoir, Razor Horizon.

Share your thoughts with Joel at onhismind@essence.com.