ADVICE: Should I Date a Bad Boy With A Criminal Past?



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Q: My bestie Googled a guy I’ve been out with three times. Let’s call him Bad Boy X. Our chemistry is crazy! And men who live on the edge do something to me. I'm 28, and I've vowed to get this out of my system by the time I turn 30. Anyway, Bad Boy X has a few warrants for things I’d rather not say. This popped up during my friend’s thorough Google search. Should I ask him about it before our next date? Or pretend like don’t know, and let him tell me when he’s ready?

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A: Since when does a grown mujer with common sense take the ostrich approach—i.e., stick her head in the sand about a situation like this? For the record, there are different kinds of warrants, such as search, arrest, and bench, with varying degrees of seriousness.

For example, a bench warrant can be issued if you fail to appear in court to answer a citation or a subpoena. But my gut is telling me this isn’t your garden variety warrant situation, and Mr. Bad Boy X is more trouble than he’s worth.

Let’s examine the facts, shall we?

1) You don’t want to disclose what the warrant is for, so that means it’s major, and you're ashamed like you did something wrong. I may be reaching, but something tells me I’m not. Hey, Bag Lady, “you went hurt your back, dragging all them bags like that.” Word to Erykah Badu. Please don’t take this person’s ish on.

2. You’re curious about why said warrant/warrants exist in the first place, instead of being turned allllllll the way off. We were taught that curiosity killed the cat and satisfaction brought him back. Yeah, that logic made sense in elementary school when we wanted to how Mikey, who wasn’t the sharpest knife in the draw, aced the math test. But as an adult, the truth may not be satisfying, and in this case, it could be unsettling.  

3. You're almost 30, and you STILL want a Bad Boy. Girl, you were supposed to get that out of your system when you graduated from high school. I’m not judging you but...forget it, I am judging you. I need you to jump out of a helicopter at 5,000 feet if you are looking for a thrill, sis.

I have questions. Are you prepared to accept and deal with the truth? Or do lies keep you warm and cozy at night? Or are you more interested in some convoluted story that’s a combination of the truth and a lie and begins with: “What had happened was”?

I’m all for second chances and believing people can change. And I don’t think we should continuously punish people for stupid mistakes they made in their youth. However, if you transgress in the same manner more than once, that’s not a MISTAKE, that’s called a CHOICE.  

This warrant sounds super recent and there’s no need to go all private eye and start stalking his social media and fact checking his story, when it bothers you that it exists in the first place. Don’t turn your life into an episode of Love & Hip Hop: Atlanta. Don’t try to save him and be the one that makes him stop [INSERT THE CRIME OF YOUR CHOICE HERE]. You had three dates. Cut your losses. Walk away (you don’t need to explain why) and make room for someone whose most serious transgression is a few unpaid parking tickets. But even he better be in the process of paying those off with the quicks.


Q: I’m a hot 50-year-old who's dating a hot 30-year-old. When we met six months ago, we agreed to keep it casual and fill our time with romantic dinners, impromptu getaways, and wild adventures. Now, he’s talking about settling down and having kids. My children are grown with babies of their own. I was married, twice. Honestly, I could fall hard for him. Am I too old for serious relationship with him?

A: Yasss. I wish you could see me giving you a virtual high-five for snagging a young tender. Vieja? Please, bite your tongue! I hear Bruno Mars singing "Versace on the floor" everytime you step in a hotel room.

I know we say age ain’t nothing but a number but…in this case, there are some things to consider. For six months, it’s been about jetting off to Paris or bouncing to Thailand, so you’ve only seen his sunny side up. You need more intel on his daily vibe, temperament and credit score. How does he react in a crisis? Is Sallie Mae pursing him with wild abandon because he has 100K in student loans? What’s his deal when you’re at work after 10 p.m. landing a big account? You've been married twice, so you know that it takes time to see someone's dark side.

My biggest concern is that this young hottie wants to be a papi. Biologically you may be able to give birth—our girl Janet Jackson popped out a son at your age, and now she’s milly rockin’ on tour and giving us #goals, but MENTALLY and PHYSICALLY you are in a different space.

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Don’t trade your sexy getaways for midnight feedings and chic diaper bags—because you already did that as a younger woman—just because you think you HAVE to do this to keep him. Relationships are a gamble. So, don’t break it off with him because you’re “too old.” Nope, you have to end it because your LIFE PLAN for the next chapter doesn't align with his. 

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