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Dating Someone Who’s Been to Prison

Dating Someone Who’s Been to Prison

Where do you draw a line in the sand that separates judgment from an inability to relate? It seems as if a lot of the men trying to date are in situations that make it hard for a woman to want to deal with them.

Before I explain further,  you can obviously  tell that not much is cooking in terms of prospects.  I may chat with the men I’m meeting online and even the ones I’ve encountered in person, but nothing sticks.  So my dating experiences haven’t gone beyond a few meet ups that have gone nowhere or I’ve just been dealing with the old faithful bench players holding it down in the friend zone.

If you know anyone who’s tried online dating and is still single, they surely have told you about the cycle.  We go away, but we come back and a couple of weeks ago, I reactivated my profile for like the fourth time this year.

Sadly, the same old song is playing.

The men I’m interested in are either cocky as hell, unavailable to date, far away (Nova Scotia is a stretch), or just not into me.

So by design, the men I am not interested in are sticking to me like flies on shit.  They are either unattractive, perverted, too thuggish or for a lack of better words- are true struggle bunnies.

Let’s take the gentleman I exchanged numbers with a few days ago who I’ll call Felonious Monk.

He’s decent looking guy (says his photos), owns a transportation business, is literate, has a great sense of humor, and the biggest score is his intellect.  He mentioned a few times how he had grown weary of the types of women he was involved with former the past, and was now looking for that “sexy, smart, corporate chick with a bit of an edge”.

That’s me, that’s me, that IS me!!!

Now while he isn’t college educated, he’s obviously spent a lot of time reading and taking in knowledge to converse about a lot of things.  I could tell he had a few rough edges, but nothing too bad was revealed from our first conversation so this one sounds decent, right?

Um, yeah.  Let’s get to that follow up call which starts out talking about living situations, kids and our backgrounds.

I’m not judging BUT 46 years old and roommate just doesn’t sound right.  He explained he was helping out a friend and not even charging him rent, so it was more of a “staying with” vs a true roommate.  Okay, whatever.  

These living situations have pretty much become the norm in California so my nose twitched a bit, but that little nagging bitch in the back of my head meowing forced me to allow what is normally a turn off and deal breaker.

The “who lives with you” talk naturally went to children and again, not judging because once again, a man with multiple children is the norm after 30, so I barely batted an eye when he said he had three.

But how many mothers?  Three.  And so it begins but gets worse.

This revelation would have had the average woman wrapping up the conversation, but I allowed the conversation to continue and then he makes a comment about people getting second chances at life.

Lord help me, I wasn’t ready.

Listening to him talk about himself and his upbringing was like turning the pages in a book on urban history;  like some “Losing Isiah” meets “Boyz N The Hood” type shit which involved a single parent household with a father nowhere to be found.  A mother strung out on crack cocaine not paying attention to what her kids were doing which led to him dropping out of school, joining a Los Angeles street gang where he hustled and sold the same drugs his mother was fiending for, and eventually – he became a career criminal.

The longest stint in prison? 7 years hence the name.

What’s so crazy is hearing how easy it was for him to get women;  the types who were attracted to that thug life which offered nothing but drama and for him – resulting in his three baby mamas.  So it’s no wonder he’s talking about wanting a different type of person who’s pretty much a square but how does that work?

I tried not to be judgmental and in spite of his checkered past, I could tell from his conversation he wasn’t a dumb man.  In fact, Felonious Monk came across as a highly intelligent, fairly articulate and driven man who claims he learned his life lessons and just wanted to live a normal life with a woman by his side.  But still…. that past is something that can’t be ignored.  Or can it?

You’ll often hear (black) women complain that there aren’t enough available men, however this isn’t entirely accurate.  They ARE out there.  It’s just a matter of how much you’re willing and able to deal with and sometimes I ask myself if I should have stayed with the bipolar, manic depressive, porn addicted, serial masturbator, emotionally manipulating, microscopic penis having ex-boyfriend instead of dealing with the dating scene.

I think it’s an inability to relate or accept those things were in the past, so I pretty much shut him down last night.

Until there’s a cure…

Carmen Jones

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Hangover - a let down following great excitement or excess. Wow. This one sentence describes nearly all of my dating and relationship experiences!

I'm a 30 year-old woman muddling through the Los Angeles dating scene and yes - Believe all that you've heard about the screwed up men and women in La-La Land.

This blog is of my actual experiences that will either make you chuckle, laugh out loud or maybe say "aw.....".

If your dating hangovers seem worse than the next person's, read on, post a comment and enjoy!



  1. Girl, I don’t blame you at all for being turned off by his past. That stuff he did was crazy. Plus, there is no point in going deeper into a situation you don’t feel right about. We have to trust our intuition when it comes to these things.

    1. True, true….it’s just crazy how they try to guilt trip you. Making it seem like our single status is a symbol of failure and from being too selective.

      If giving the side eye to someone who’s got more strikes than a pitcher is wrong, then so be it.

      Single until there’s a cure.

  2. This isn’t even a question of maybe for me – it’s a no dawg.

    It sounds messed up but sorry, I want no dealings with someone who’s been locked up once let alone a bunch of times. Even if he’s a solid dude it’s those prison elements I would be concerned about. It’s crazy to even consider it and remember how most men aren’t even checking for a woman unless she’s got a big booty, sending feel bad if you’re not feeling his shady ass past.

    1. Well when you bring up how picky some men can be over trivial things, you’re absolutely right. I’m leaning towards the no. And your name- love it!!!!

  3. I wouldn’t necessarily knock someone for having been to prison but if depends. What did they go for and were we already together. If that’s someone I’m involved with I’m not just going to drop him. Not sure if I want to get to know someone for the first time though. Maybe give him chance. Maybe.

    1. I hear you and I didn’t blow him out the water right away. Oh… and definitely a different situation if my boo went to the clinker while we were together, as long as it wasn’t for something crazy.

  4. So I’m finding myself in this same position and normally I’d be like “sorry no can do” BUT much like your felonious monk, he is intelligent, articulate, college educated, and we have fun. His situation was a little different, multiple DWIs. He explained he was dealing with the loss of a parent in all the wrong ways. I’m struggling with the fact he may not have been a “thug” but he still did A,B, AND C to get himself locked up (less than 6 months). Am I naive for considering overlooking it?

    1. S,

      I feel you on this and for me, deciding if I can deal with someone with a checkered fingerprint history depends.

      What did they do, how long were they in and how many times did they do it?

      White collar crimes I would be more lenient with, drug offenses (weed for recreational use or even distribution, maybe even the others), I’m raising an eyebrow.

      Robbery, violent crimes and sex offenses? Hell to the no.

      Now it’s been a while since you commented (blame Spam filters, my bad), I’m wondering if you and your guy are still going. My question for someone like that would be “So when are we going to AA?”

      Multiple DUI’s is a problem because people could have been hurt or killed AND those are just the times he got caught. I would be wondering how often he (1) gets smashed and (2) what kind of debt he’s in from all of those court fees.

      Not the worst felon but definitely a scary one who may not have learned the lesson.

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