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Sex & Relationships

Should a Man’s Past Drive a Woman Away?

In my recent post “Should A Woman’s Salty Past Be A Deal Breaker?” I touched on some skeletons that women may have in their shoe closets and whether or not they (the skeletons) should play peek a boo; and if so, should a man leave or continue to pursue something with the woman. So I’ll be doing the same with the not so fairer sex, and I’ll incorporate the same rating system with different vernacular although I won’t rate them. I’ll leave that up to YOU the readers. For each scenario is it:

* Yay?
* Nay?
* Run away?

So people, what say you? Here goes…

1. Was gang involved

This is a situation where a man can definitely turn himself around and live a life as an upstanding citizen. Gangs are a pretty serious epidemic and has been plaguing inner cities (even some suburban areas) all across the U.S. for decades. And in this case, if you’re dealing with a man who used to be heavily gang involved it’s a tough call.

Was he the enforcer who more than likely has a body if not many? Was he just the ‘runner’ who ran the drugs? Was he a street soldier or ‘Nino Brown’ himself? Chances are this may not come back to bite you, but if he engaged in this recently, you have to ask yourself,… “Does he still have enemies? If so, will I be targeted? Does he still acquaint himself with those same men?  If we get serious do I have to worry about him reverting back to his old ways?”

If he was like Ving Rhames’ character “Melvin” from ‘Baby Boy’, he was reformed. Not to mention you’ll get your fair share of breakfast in bed and if your son is mouthy he’ll get punched in the face. Win-Win right? LoL! I won’t go into this though, that’s up to you. See for yourself.

2. Domestic Abuse

Domestic Abuse 2 - OpinionatedMale.comNow gents, I understand women  – especially in this day and age –  can become very loose at the lips and outright belligerent. Believe me, I’ve seen it. I am not in any way shape or form condoning a man hitting a woman. If she strikes him and is coming for more, then he has a right to defend himself in some way. I don’t mean match her blow for blow though. Restraining her is preferred.

I also recognize some men could have done this ONE time to ONE woman in the heat of a serious moment and never again. However, what would contain him from doing it to a second woman …or you? On top of all this you might wonder, “Does he have a temper? Does he have a history of beating his women”?

3. ‘Step fathered’ his family

No spoiler alert here but if you watched any of the [Step Father] movies, you know what I’m talking about. If you were ever privy to this ‘type’ of info about a man – not to sound blasphemous in the least – but I don’t care how many times he has found Jesus, Do….Not…Do…It!

* I will say Terry O. Quinn did a superb job in the original movie.

4. Used to date or slept with a friend/relative

Sometimes men do things in life they later regret, and some of these transgressions they may make a precious few [individuals] aware of them. Other times they may take it straight to the grave.

Now ladies if you had a man (or met a man) and became serious with him only to find out he had relations with a close friend or relative before you, what do you do?  Is this a deterrent? Does the ‘giraffe theory’ come into play – meaning if you didn’t see it or know of it at the time then it didn’t happen? Who knows, maybe he wasn’t aware that was your friend, or distant relative. I mean how often are we spitting images of our cousins, nieces, or nephews?

5. Alcoholism/Drug Abuse

Similar to what I mentioned in my previous article about women deal breaker’s this shouldn’t be an issue. As long as he remains clean and sober, I say no worries.

6. Cheated in a previous relationship

cheating man caught - OpinionatedMale.comNow see, talking about this sucks and I am sure I can speak for others out there.

What if a man meets a woman who was virtually everything he could have asked for? She was a blessing from above so to speak. They had one of those conversations and he were very open and honest with her about his past and revealed this info. Orrrr, a worse scenario is if the young lady received this information from another source, in which case he might be portrayed as being even more deceiving.

In the end, I’m pretty confident knowing that the average Joe would perhaps become dispirited if he felt he had a legitimate shot at this woman, but because of something he did in the past, it turned out to be all for naught.

7.  Has ‘beef’ with someone in your family

Truth be told, this happened to someone that I knew. Without disclosing too much of what happened, he had serious issues with his girlfriend’s brother. And to say it caused lots of friction at family events they attended is an understatement. The once close relationship she had with her brother was splintered for a long time. Although the issues between her brother and her beau was squashed there was still no love lost.

There are two schools of thought on this: If the two of you hit it off and blossomed into something special then it shouldn’t matter, that’s your relationship. On the other hand, if it involves a member of your immediate family, think of the ramifications it may have. Do you want to feel like you have to choose between the two?

8. Had tons of sexual partners

Sexual Partner Count - OpinionatedMale.comWe as men are labeled everything under the sea should we have a high count. Yes, so are women. However, I ask you this ladies:

If you met a man and things were going well and moving towards a relationship, what would you do if that conversation popped up? Would you stay and see if you could turn him into a ‘one woman man’? Tame the proverbial wild stallion and consider it a victory of some sorts?
Would it be fair to assume women don’t care because either they feel it’s in the past, or they have a pretty high number of partners themselves so his number wouldn’t matter either?
Question: What would you consider a high count for a man who is 25? 35? Older?

9. Previously ‘messed around’ with a man

So he did this back in the day whether by experiment or an actual sexual relationship, but he’s no longer on that side of the neighbors yard. He’s everything you’re looking for except for that ONE hitch. Hmmmm? Deal breaker?

So with all that being said, ladies what is your take on these skeletons of men? Yay? Nay or Run Away? Could any of these be tolerable? Any additions?

Gents, if you have any of these in your experiences and said woman found out, how would you handle it? What would your approach be?



01/15/19 Post title updated. Original title, “Yay or Nay: Should a Man’s Salty Past Drive a Woman Away”

My motto is, "Live, love and laugh". Check me out in the "Men Behind The Pen" section on


  • Soulflower

    Excellent piece and I would love to comment on this one, but I came to work an hour earlier to get caught up on my work and I haven’t done much but read this post so far. So I’ll get back to you, but really like the piece and your site.
    I now understand how some of the men reacted to the Woman’s Salty past issue, most of these things would be serious deal breakers for me, especially the “messed around” with a man thing. Too many down low brothers out there for me!!!! And with Aids too? Not feeling that.

    • Cortonio

      Looking forward to your commentary. And yes unfortunately there are a lot of ‘down low’ brothers out there, in which case it’s an indictment on them for not accepting who they truly are and trying to be someone they’re not.

      • Soulflower

        AW, who am I kidding? I am not dating anyone, haven’t for more than four years as I am of the age group where the men are looking for younger women and no one wants to date a mature woman. But I genuinely love reading the comments from you youngun’s about how life is out there now. I’m just thankful I made the most of my youth so I have no regrets now.

  • t-roy

    All but one, #8 i’ve actually talked too girls that applaud a guy with a high count. It shows “he gets what he wants” and allot of women find that attractive. The player will always have his way with women and power too him. Gang involvement should be dismissed if not forgotten. 90% of kids who join a gang have no family to fall back on for that necessary love and structure needed for proper growth. Exception, if your talking to him now and his in a gang thats a big NO-GO.

    • Cortonio

      Indeed, women tend to find that attractive because some women like the novelty of competition, and you know the saying “no body wants you unless you have someone” Although one could lie about his partners as well. Yes I agree with the part about children using a gang as that ‘family’ however as much as women love bad boys I don’t think you want to be in a situation where their new man or potential new man still has ties. See: Aaron hernandez

  • Barefootcountessa

    Very nice post. I think the content of this article can relate to women as well on many levels. Relationships are so difficult to judge at times and you shouldnt feel pressured to tell all in the first instance. Get to know the person first and if their revelation about the past is workable between you two. Then great if not, run lol

    • Cortonio

      Ladies welcome to OM. Like the work you’re doing on your site. As far as your deal breaker goes… It’s weird because some women actually told me they’d let that fly. Well different strokes for different folks.

  • E.B. Davis

    Great article. The DV piece to me is a big NO. Unless he has underwent tons of therapy. Since temperament is something difficult to change. I believe people have the ability to change, so I will try to give someone the benefit of doubt, but once a zebra shows you his true stripes you are best to believe him.

    • Cortonio

      Thanks welcome to OM.
      I am inclined to agree because DV is also something that is seemingly chemically imbalanced and ingrained into you. And especially being something that you watched growing up it becomes a cycle.

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