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Dear Wendy

Should I date the jailbird?

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  • #841754 Reply

    I am a long-time lurker at this site and am finally making contact because I could use some input from strangers to help sort my feelings out.

    I haven’t entirely figured out what I want out of this, but am hoping typing my thoughts out will help me do so.

    Okay, backstory time – I will make this as brief as possible, while attempting to include as much detail as I can. At the beginning of last year I met a guy through Tinder with whom I started a casual thing. He is of a different race and has a different background to mine, and moved to my area to attend school and build a different life for himself the previous fall. I was out of work at the time, and he had a lot of free time, so although we were only casually involved, we saw a lot of each other. After about one, maybe two months, he informs me that he’s going to jail. He’s been sentenced to a minimum of ten months, and is waiting to serve his time. At the time of telling me, he was due to go in about a week later. He then got an extension, pushing the start of his prison-time back to June 1st.
    Needless to say, I was surprised. I don’t know a lot (if any) other people who’ve been to jail, and am about as clean-cut and rule-following as they come. But by this point I knew him, we’d talked a bit about his background, and while he hadn’t mentioned the crime-committing aspects, the way he reflected on his choices made me trust he was serious about breaking from his old life. I still believe that. So we continued casually dating during the spring. I had from the start made it clear that this was a casual thing to me, and this was cemented when I found out about him going to prison. I did however tell him that I would remain his friend through this, regardless of what else happened with us.

    Of course, I’d not be writing a long-ass post on an advice forum if things remained as clear-cut as that. I had a tough time during that spring, and he was a good support for me, mostly by distracting me when he saw I needed it, as he respected that I didn’t want to delve into it. So we grew close.
    We’ve communicated through letters and the occasional phone call for the time he was in high-security. When he was moved to low-security he was granted leave (we’re in Europe, it’s a thing), first for a day, then an overnight visit. And it’s after these two trips it has properly dawned on me that I’m ‘in trouble’, as I like to put it when I catch feelings. I am falling for this guy. So that’s where my heart is. My head is confused.

    We’ve always been in a bubble, where we’ve not had to deal with real life. First I was out of work, then he was going to prison, now he’s IN prison. When he gets out and gets fully started on his studies will be the first time we’re both living life normally. My decision as of a few months ago was to maintain purely a friendship for the start of that phase. That way, I won’t become his sole support system (I am great at being the support system, and have historically also been great at volunteering myself for that kind of job, even at the cost of my own sanity sometimes – I’ve done serious work to stop that instinct), and I can assess if he’s able to make this change before committing fully.
    But now, I’m not sure I want to. The last few people I dated seriously all ended because I couldn’t figure out how I was feeling or too scared to act on how I was feeling. This time that isn’t an issue. I feel like I owe it to myself to let my heart lead instead of my head for once. But at the same time these circumstances are completely different.
    He used to be in a gang-like environment, with all that entails in terms of culture and social norms. Very different from how I’ve lived. I know he’s in the process of shifting his values, and that I can be a huge influence on that process, but at the same time – that is a big undertaking. Being emotionally attached to someone going through such big changes can end very badly. I am very aware that my faith in his ability to do this is likely to be biased and based in rose-tinted glasses. That’s why I wanted to take a step back for a time to let him get started on his own. But I don’t know if I want to wait that long. Especially not if it means he moves on and finds someone else.

    I guess what I would like from yous all are some thoughts on what I need to consider in order to make a good decision here. What topics would he and I need to be on the same page about, what would be deal-breakers to you, what do I have to think through and weigh against each other on my own. Wendy unfortunately doesn’t have a handy ’20 things to think about before dating an ex-con’-list, so I’m hoping you all can help me put one together, an give me an outside perspective.

    #841757 Reply

    I think the time to figure this out was probably after the month or two that you knew him and he finally told you. It kind of sounds like you’ve already decided you have feelings for him, and are probably going to try this. And given your history of being the support system, that’s most likely the role you’ll fall into. Right? Have you made plans with him for when he gets out?

    The one thing that would make or break this for me would be- what crime did he commit?

    How will this affect his future? What about job/career stuff? Will this remain on his record? Is he on probation?

    #841760 Reply

    Yeah, what crime was he locked up for? I think that’s relevant.

    Also, Wendy may not have a list like that, but such resources must exist on the internet.

    My take on this is, whatever he’s *said* to you, he hasn’t demonstrated through actions that he can be the guy you want for a life partner. Only time is going to be able to show you that. And he may run into significant challenges and obstacles to gaining employment. Furthermore, you say he’s “in the process of shifting his values.” He’s not even there yet mentally. And you also say you’ve always lived in a bubble with him and not dealt with real life.

    I feel like you’re motivated to go all in on this out of fear of losing him, and also your tendency to want to be a savior. Those are danger signs. He’s a project. You’ve got rose colored glasses on. None of this bodes well for the future or your ability to make a decision.

    I think the right thing to do here is NOT to make any declaration that you’re going to be together. You should take that step back and let HIM show YOU how he wants to live, and the actions he’s willing to take. And if he jumps into a relationship with someone else because you have him that space, this was never meant to be, or not at this time.

    Don’t jump in and be a savior out of fear.

    #841766 Reply

    I agree with anonymousse and Kate, and find it telling/suspicious that you didn’t say what crime he committed to get himself sent to prison.

    If you really do think you have a long-term future with this person, you absolutely SHOULD take a step back, pump the brakes, etc. Treat it as you would if you were considering a relationship with a recovering addict. Conventional wisdom is that addicts should not be pursuing relationships until they’ve been clean for a year or so. He needs to turn his life around *all on his own* before you come swooping in to be his savior/crutch. If you truly have a future together, keeping it friendly/casual for 6 months to a year is nothing. If he moves on to someone else, he’s not the guy for you anyway.

    #841769 Reply

    A high security prison is for big timers, he must have done something bad. I would move on, like you know he needs to go back to his studies to get an education for a job he might not even get because of his criminal record. You will be supporting him your entire life that you are going to be with him. The best job he might get is being a factory worker or flipping burgers, and the factory worker is a far fetch. Its all up to you on how you want to live the remainder of your life, being an adult babysitter/provider just for some excitement or find someone that is not a criminal and has a good job and can look after you if you ever lose your job and need to find another job.

    #841770 Reply

    You really do need to KNOW he could do it on his own. It’s not enough to see him again asking positive steps with you pushing him (which i don’t even know if you have yet), because then you don’t know the extent to which you’re a crutch.

    #841776 Reply


    #841778 Reply

    “In process of shifting his values” really says it all. He’s not changed, then?

    You’re worried that if you take a step back, he’d find someone else. That’s pretty concerning.

    I’d also echo what was said about you having a savior complex. This is not a healthy foundation. You know this situation has multiple red flags.

    #841779 Reply

    Wait, so he’s been in prison this whole time, and you met him while he was on leave (not understanding he was actually incarcerated)? I’m confused.

    Regardless, he’s been dishonest with you. That’s not a good start. And, you need to know what he did. Ten months (in Europe, in high security), that’s not a jay-walking ticket. I don’t know privacy laws in Europe, but in the US, you could 100% find out what his crime was for without you having to ask (or you could verify what he tells you).

    I don’t know, I’m not against dating a former convict, I think people can and should be rehabilitated and not treated as lepers for the rest of their lives, but he started your relationship on a pretty substantial lie. That’s a really big red flag.

    #841780 Reply

    “The last few people I dated seriously all ended because I couldn’t figure out how I was feeling or too scared to act on how I was feeling. This time that isn’t an issue. I feel like I owe it to myself to let my heart lead instead of my head for once.”

    This isn’t you deviating from your previous pattern. You’re still sabotaging your romantic life. Instead of being the one who is emotionally unavailable to have a relationship, you’re choosing to go into a relationship with someone who probably can’t provide you with a stable, healthy relationship. These are two sides of the same coin. If you were truly deviating from your previous pattern, then you’d be interested in a stable man who you can be in a healthy relationship with. Someone where you don’t need to ask an advice website if it’s OK to pursue him. (Also, some people think they are unnecessarily sabotaging relationships, when in reality, they just get too far into relationships with people they shouldn’t and find out they aren’t into the person. It’s hard to say whether you are ending good relationships or if you just sort of jump in with people you should be turning down, and then tell yourself it’s your fault for losing interest. But either way, it’s not going to be solved by getting together with a guy in prison.)

    As someone who finds prison/crime life very foreign, I hope you understand that it’s very possible for him to be lying to you about a lot of things and that you might not be able to tell the difference. Taking everything he says at face value is incredibly naive.

    There are billions of men in the world, and many of them have not gone to prison. No need to go looking for trouble.

    #841781 Reply

    Moving to a new city was probably a way to separate himself from the people he was getting into trouble with so a good sign. Going to school is also a good sign.

    Now you need to ask yourself the difficult questions. What crime did he commit? What could pull him back into his old life? If his parents got sick would he feel obligated to go back to take care of them? Would that put him right back into the middle of everything? Does he owe anything to anyone involved in crime? If so, do you have to worry about anyone showing up at your door making threats? Has he turned anyone in? Again, if so do you need to worry about anyone showing up at your door making threats?

    You need to see if he is able to keep himself separate from his previous life. You need to see if he can finish school and you need to see if he can get a job. In the US if you’ve committed a felony it is incredibly hard to get a job. I don’t know if Europe is the same. You need time to see how he turns out. If you feel that you must jump into this relationship right now or lose him then it is better to lose him. If you can be good friends for a while, meaning enough years to see if he finishes school and gets a job, then be friends until he proves himself. Only get involved romantically if he has proven himself able to live a life where he isn’t pulled back into his old group and where he can financially support himself.

    #841782 Reply

    It depends what he did. People go to prison for using drugs, people go to prison for assaulting and injuring others. For being in a fight which turned bad due to a fall and resulting head injury, or a fight which turned bad because they stabbed someone.Or for fraud.Or theft. None of these things are exactly ideal but neither are they identical.Without knowing what he did I couldn’t advise at all.

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