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Dear Wendy

Should I date the jailbird?

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Viewing 12 posts - 13 through 24 (of 57 total)
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  • #841784 Reply


    Really, no.

    In part because he’s a bad risk, but mostly because of the reasons you’re contemplating it.

    It’s so easy to see in your letter that you see this as some kind of grand romantic chance, where your love will save him. You feel like you haven’t allowed yourself to be open to relationships, so you’re going to break that pattern by taking the biggest, riskiest leap you can.

    You didn’t mention what he’s in jail for, and I think that’s fairly telling. You didn’t think we’d react positively, and you want us to tell you to take the chance. I can’t do that, because I wouldn’t take the chance in your position. There are loads of guys out there that you can take a chance on that don’t have the baggage this one does.

    #841786 Reply

    I mean, *definitely not* if it was sexual assault or domestic abuse.

    But even if it was something less egregious, I think the considerations here point to not getting into a relationship at this time.

    #841788 Reply

    Don’t do it. It is not worth it. I speak from (secondhand) experience. My best friend from college married her college sweetheart (also a good friend) who ended up TRULY unknowingly and, frankly, stupidly, committing a white-collar crime and was convicted for it and sent to prison. They were married for 5+ years before he went inside, but their entire marriage has been clouded by this. He gets out in September and while they have stayed married, my friend is a saint/martyr and I honestly believe she should have divorced him, much as I like her husband as well. He will never, ever be able to match her in income and be an equal contributor in their household in any way. He will have YEARS of therapy to go through to counteract the PTSD he is feeling because of prison. The reason(s) he was sent to prison – ignorance about the way the world works and stubbornness/unwillingness to learn – are deep rooted and has taken my best friend her entire marriage trying to uproot, and they are still present. He is not an equal partner in any way and never will be. (There are other reasons why I truly believe she should have divorced him, but it’s not my story to tell.) They fell in love and got married BEFORE this happened. Why would you sign up for it willingly? Trust me when I say you cannot “save” him, your “special love” is not enough. Oh, and my friend is in the lowest of the low security in prison and it is still an absolute nightmare. I can’t imagine what this man has done to get him in high security. (!)

    #841789 Reply

    I should add a disclaimer here…many years ago, I dated a guy for awhile who had a felony record for theft. It was a dumb college guy stunt, he did about a month in jail and was on parole when I met him.

    He was a thoroughly decent guy and 100% understood the stupidity of what he’d done, and was committed to never doing anything like that again. But…the immaturity, attraction to risk-taking and poor impulse control that led him to do the dumb college guy thing were still very much with him. And that’s why the relationship ended.

    That’s the question I’d have in your position. What did he do, why did he do it, and what about his personality/circumstances led him to do it? And has any of that changed?

    #841791 Reply

    You wrote that he doesn’t mention the “crime committing aspects” he took part in. So, do you know why he went to prison? Do you know what kind of criminal activities he was involved in? I think if he was really trying to change his life and give his relationship with you a real shot, he’d be upfront and honest with you about his past.

    #841792 Reply

    Well, shit. I wrote a reply to Anonymousse before leaving work, but it must not have gone through. Well, bright side is I can try and answer more of your questions at once. Can’t be arsed writing them out completely, though, so I’ll bullet point this slightly.

    – I do know what he did. It was a violent crime, but not domestic violence or sexual assault. I was very clear I needed to know what he did before even considering continuing to see him when he told me. He told me the whole story, didn’t hesitate to answer my questions. The way he talks about his past is what made me trust his response; he can reflect on what he did, and while he does think his decisions were stupid, he doesn’t shift blame or excuse what he did. We’ve had many talks about his past and his background where he continues to reflect on who he was then vs who he is now.

    – I say he is in the process of changing, because change is just that, a process. Shifting your entire set of values is something that takes time. But you’re right, he’s not done, and while I want to be able to have a positive influence on this process, I don’t want to be dragged into it, nor do I want to be in charge of it.

    – No chance of anyone showing up at my door causing a threat, as far as I can assess. But a worthy point to consider! His parents are both dead, and while he does have family in his old city, they all have others to look after them if the need were to arise.

    – His future is not as limited here as it would be in the States. He is continuing his higher education in prison, and I’m pretty sure there is a clear limit to what kind of jobs can require a transcript of your criminal record before hiring. Though I will definitely look into it more, as it’s not something I know an awful lot about and is a very valid concern.

    – Urgh, the term saviour complex hit me hard. Yeah, I have had a habit of putting others before myself, though not really when it comes to partners. More in the over-achieving, work-related and volunteering type of way. I think that’s why I’m worried. There’s an emotional element here that could potentially cloud my judgement when it comes to setting boundaries, which I am now pretty damn good at on other fronts.

    – Whoever it was that said my pattern hasn’t really changed: You know, that dawned on me too after I wrrote this. Nail on the head. I’m so worried about repeating the mistake of letting my over-analysing head rule every situation I’m prepared to make the exact opposite one! I’m just not used to maneuvering these kinds of decisions while feeling like this. But this is in fact an opposite situation to the ones I’ve been in before. Which means that keeping my head in charge is the way to go.

    I continue to see a lot of growth in him, I know he must’ve changed a lot before we met, cause the man he talks about is not someone I’d even entertain spending time with, but he’s also changed so much in the time I’ve known him. I don’t question his dedication to this new life, but that doesn’t mean I shouldn’t set my boundaries to make sure he’s on the road to succeeding at it.

    So what does that mean exactly? What am I looking for, to confirm this change will stick? Progressing at his studies is a given, as is securing work and being financially responsible. Not committing crimes, of course. What else? What am I forgetting?

    #841793 Reply

    I think you should look for him to be the partner you want and need. Like actually BE that guy, not in some degree of transition. Don’t fall in love with his perceived potential.

    #841794 Reply
    avatarMiss MJ

    I’d definitely move very slowly here. The reason people say “don’t date a (or date as a) newly recovering addict” is because that person is in the process of transforming and they need to focus on themselves and that process, first and foremost, in order to get a solid foundation from which to regrow. I imagine it’s much the same for a former inmate. This guy is going to have to rebuild his entire life, from the ground up. New friends, new hobbies, new job, new city, new way of thinking, living, being — a new everything, basically. And for him to develop all the potential that you see in him/he sees in himself, he needs to be able to focus on himself and do that. Becoming dependent upon you (emotionally, financially, whatever) is likely to actually stunt his growth and impede that process. I’d say take a giant step back. Be a friend, sure. But dial back the romance and the expectations, too, frankly. Addicts often stumble. Former inmates do, too. That’s not to say it can’t be done. But this is going to be a hard road, with many bumps along the way.

    #841796 Reply

    I don’t know that if I was in your place, that I would have continued to see him after waiting a month or two after you met to tell you that he was (at that time) going to prison in a week.

    It seems like there’s kind of a slippery slope with how he determines to give you information. For those reasons along with all the others, I would recommend taking a step back and seeing what happens. Don’t be the person he’s coming home to. Don’t house him. Don’t date him when he gets out. Wait and see. If he finds someone else, then that’s that. It is interesting that this one guy makes you want to forgo your normal caution.

    You said it was casual, that you wanted to be friends for now…but have you been? Have you dated anyone else? Asked your friends or family what they think? Just curious.

    #841797 Reply

    What @Kate said was very, very wise: “Don’t fall in love with his perceived potential.” You paint this very rosy picture, but is that a picture of him now, or what you feel he’ll be when he completes this process? If he’s not 100% the right guy for you today, he’s not the right guy.

    As for the other questions you asked, such as “What am I looking for, to confirm these changes will stick?” The only way you’ll know that is in hindsight – 10 years on, have the changes stuck? There’s simply no way to predict that today. I’m sure everyone thinks the positive changes they make in their lives will stick.

    Other than that, I’ll just reiterate what I said in my earlier post. The personality traits that lead to bad choices (gang involvement, violence) are very often the same traits that make someone a really poor boyfriend. Just acknowledging that he did the wrong thing is not enough to know that there won’t be other, different bad choices.

    #841798 Reply

    Yeah, one of the common themes on any advice site is don’t date anyone expecting them to make big changes.

    #841799 Reply

    Honestly I don’t know still.

    He started this relationship with you under false pretenses. You might argue it was just a lie of omission – but withholding that you are about to be imprisioned for a year is a pretty freaking huge omission, in my book. If it were me, I don’t think I could trust him and wouldn’t ever feel comfortable in the relationship.

    But I guess if you’re committed to seeing this through – I’d say you need to go in with your eyes wide open and trust your gut. You need to look past your infatuation and be clear eyed about this whole thing. If he gives you any reason – ANY – to feel he’s still being less than truthful or isn’t honestly working on moving beyond his past and background, I’d be prepared to cut bait.

    Maybe he is truly working on bettering himself, and if so, that’s laudable and what we want people to do. It’s not fair to stigmatize people forever when they have put in the effort to better themselves and rise above their past.

    But eh – this all seems relatively fresh. Right now all you have are promises, not actual results yet that he’s going to be able to turn it around. The lie for me is a pretty clue that he’s got a ways to go.

    If you stick this out you should remember – this is on him to get on the right track. If he ever strikes you as being duplicitous or if slips up, it’s not your job to hold his hand and help nudge him back to the right path. Don’t make yourself a martyr for this guy if he won’t, or can’t, get it together.

Viewing 12 posts - 13 through 24 (of 57 total)
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