Dear Wendy
Dear Wendy

“Should I Reach Out Now That He’s Getting Out of Jail?”

jail love
Years ago, I dated for a few months a guy who I knew had made some mistakes in his past before he met me. He was an amazing partner: thoughtful, funny and very supportive during our relationship. The little things he did for me showed me that I meant something to him. Our relationship was cut short, however, when he was jailed for armed robbery back in 2004. He wrote to me when he first went in, but, because I was truly angry and disappointed in what he did and because I thought that he would never get out, I didn’t respond.

I am now 32, and I have always thought about him and wondered what our lives would have been like if he hadn’t been locked up. He’s been on my mind so much lately that I found his profile on a website called loveaprisoner. Should I reach out to him? It looks like he will be getting out relatively soon. I don’t want to be duped again if he hasn’t been rehabilitated, though. Any advice you give is greatly appreciated. — Missing The Jail Bird

Eleven-plus years is a long, long time, especially considering you only dated a few months, you haven’t been in contact this whole time, and you have no idea what this guy might be like after spending over a decade locked up. (Here’s one story, written by a DW reader, of some of the challenges she faced when her husband was released from prison. It was hard for them and they had the benefit of a strong relationship and regular contact while he was in prison, two things you do not have with this man).

If you decide to reach out to this guy, you certainly need to manage your expectations and be clear to yourself what your motives are. It’s easy, especially when we’re lonely or it’s been a while since we felt a true connection with someone, to romanticize someone from our past. But this guy has, for all intents and purposes, been dead to you for a long time, and you know what they say when someone you love dies? Their flaws suddenly disappear. I’m sure this man had flaws. And for all you know, they may be deeper and more intense after all these years he’s been in jail. He will likely face challenges in readjusting to life on the outside that will make investing in a new relationship a near impossibility — at least for a while.

I would only recommend you reach out to this man if you can do so with the intention of only being a friend. But when you use language like “I don’t want to be duped again,” it seems like you’ve already decided what kind of relationship you want with him and, if he fails to meet your expectations, you’ll be angry. Spoiler: He’s probably going to fail to meet your expectations if you try to rekindle a very short relationship from a decade ago at this juncture. If, a year after he’s been released from jail, you’re still thinking of him and wondering if there might be something between you worth exploring, by all means look him up. But keep in mind that he may very well not be the man you remember. The truth is, the man you remember may never have existed.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.

32 comments… add one
  • Miss MJ October 13, 2015, 10:54 am

    I think Wendy’s advice here is solid. It’s a really bad idea to try to start something romantic (and you do want something romantic) with this man right now, for both of you, really. He’s got a lot to sort out and should focus on putting his life back together. And you shouldn’t go into a relationship with preconceived notions and expectations of who this person is when you cannot even begin to know whether he can – or even wants – to meet them. It’s not fair to either of you.

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  • chief10 October 13, 2015, 10:56 am

    I’m caught up in that…just by pure chance you were on loveaprisoner.com and you just happened to stumble upon his profile. I’m just getting the feels that you are just trying to cling to this memory of the last time you were happy with this guy. Me personally I wouldn’t give a second thought to someone who went in for a decade for ARMED ROBBERY no matter how great they made me feel in a several months only relationship. Aim higher.

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  • Wonderland October 13, 2015, 10:59 am

    The man you’re fantasizing about and the man he is are not the same person. Your own language says you wonder what your life may have been “if he hadn’t been locked up”…you mean if you had been dating a man who had the moral fortitude to not commit armed freaking robbery….

    Walk away, dear.

    I’m not saying this because a person who has been incarcerated doesn’t deserve love, grace, patience, and all that stuff…I’m saying it because you WILL get hurt because you don’t have a realistic view of his and your relationship, who he is and who he was.

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  • Ron October 13, 2015, 11:04 am

    Sort of what Wendy said, but don’t even try to contact him with the intent of being a friend, because he’ll try to suck you in and you seem very willing for more. Nothing good can come of this. An armed robber is a violent person. You saw the best of him for a short period of time. Very unlikely that is the real him. Do not throw your life away, just because you are bored, lonely and feeling nostalgic. I also agree with chief10: who spends her time on loveaprisoner.com until she just happens to find a guy from 11 years ago? That’s just insane. Loving a prisoner is not like adopting an abandoned kitten you found along the side of the road.

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  • Stonegypsy October 13, 2015, 11:43 am

    Yeah, this is a bad idea. It sounds like you are lonely and are looking back at this relationship from 11 years ago because… he was a good partner, for the three months or whatever you dated? It’s really easy to be a good partner for 3 months. Anyone can do it.
    Try OKCupid or Match, instead of loveaprisoner.com. You’ll find better and more available partners that way.

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  • FireStar October 13, 2015, 11:43 am

    Should I reach out?

    No. And for all you know someone else has been loving that particular prisoner the last 11 years. Find someone else. Preferably not a violent, ex-con who will have trouble assimilating into society.

    If you absolutely insist on contacting him then wait a year or two to see what type of man he actually ended up being. You didn’t really know before when you were 21- and if you believe he is more than (maybe) the worst mistake he made then you have to wait and see what he does with his second chance. Not worth waiting two years for? Then not worth it period. Move on.

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  • dinoceros October 13, 2015, 11:45 am

    I have empathy for folks who are incarcerated in our crappy correctional system, so I don’t want to imply that no one should ever be with them. But YOU asked for advice, so I’m going to respond based on what seems to be good for YOU specifically.

    I feel like you’re looking for trouble, you know? Like it’s one thing when you’re currently involved with someone and have to deal with this stuff, but to be so far removed but want to reconnect is another. You mention that you wonder what would have happened had he not gone to jail. Of all the things you can think about regarding this, it’s the least productive. Because the fact is he DID go to jail. It’s like wondering what your life would be like if you were born on the moon or your family was super rich. It’s not factually true, so it has no bearing whatsoever on your current life. He’s also not the same person he was before.

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    • RedRoverRedRover October 13, 2015, 11:58 am

      He’s also probably not the person she thought he was, ever. You only dated a couple of months. That’s “best behaviour” time, when people aren’t showing their real selves. Did you have any idea he was a violent criminal? I’m guessing not. For someone to do that kind of thing requires a certain mindset, or extreme desperation. Were you aware of either of those things? Again, probably not. You didn’t even really know him yet. All you saw was the version of himself that he showed you. If you get back together with him, maybe you’ll see that version again… for a few months. But eventually he’ll show the real him, which is a person who is open to committing armed robbery. Not to mention how he may have changed while in jail. I mean, he’s spent most of his adult life in jail so far. Do you really think he’s just going to pop back into that old persona you remember with no problems?

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    • Cleopatra Jones October 13, 2015, 12:26 pm

      And he could have changed in a good way. This guy could now be focused on being a better person, he could have found or renewed a faith in a religion, or is focused on getting into a better financial situation. Honestly, she may not even be on his radar because he wants nothing to do with anyone from his old life.

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  • Juliecatharine October 13, 2015, 11:53 am

    Honey, there’s desperate and then there’s ‘happening upon’ a dude you barely knew over a decade ago on a prisoner dating site. You need to aim higher.

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  • SasLinna October 13, 2015, 12:34 pm

    Getting back in touch after 11 years – generally not a great idea.
    With a a guy who spent jail time for armed robbery – extra no.

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    • Kate October 13, 2015, 1:20 pm

      It’s a prisoner *pen pal* site. An alert reader just texted me a screenshot of it. It has a 75% compatibility rating for those looking for their soul mate.

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      • SasLinna October 13, 2015, 1:29 pm

        Did you mean to respond to honeybeenicki?
        I totally missed the part about seeing his profile on “loveaprisoner”. Why is she browsing that site at all?

      • Kate October 13, 2015, 1:34 pm

        Oh yeah, I meant to reply to JulieCatharine, sorry. She may have been browsing it specifically to try to find this guy? If she was browsing it to find a prisoner pen pal, I would wonder why, and what’s wrong with regular dating sites.

  • anonymousse October 13, 2015, 12:39 pm

    When I think of the person I was 11 years ago, (21, youthful and naive as hell) and look at all the experiences I’ve had and things I’ve learned and places I’ve lived…you would not see the same person. He’s not the same. I doubt you had an accurate picture of who he was then, but both of you have grown into adults now. He wasn’t the most thoughtful or the kindest or whatever you thought he was. He did something so violent and harmful to to be put in jail for 11 years. Not even sentenced for 11 and let out early for good behavior or whatever. 11 years. I feel like there’s definitely been people who have killed others and gotten less time. Maybe if you haven’t, you should research his crime and find out what really happened. Contact the lawyer who represented him, his parole officer or look up the court records. Maybe that will help turn you away from this really (probably insanely) bad idea. Even if he was a saint and got locked up for 11 years, think of the problems and drama he is going to have readjusting to life outside. He has no job, no savings, he might be confined to house arrest or other restrictions….oh and you don’t know who he is anymore! I think it’s best if you lay the past to rest and go on match.com, okcupid or whatever and find a man who is available to date, drive and isn’t on parole. Just my two cents.

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    • anonymousse October 13, 2015, 12:42 pm

      FWIW, I do think people can make mistakes and turn away from a life of crime or learn from them, but he’s been incarcerated for a long time. You don’t know who he is anymore. You didn’t really know him then, and he’s spent 1/3 of his life locked up with other criminals. This is a bad, bad idea.

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    • RedRoverRedRover October 13, 2015, 1:40 pm

      Not to mention that not only will she see him differently, but *she* is a different person too. 32 is a hell of a lot different from 21. Who’s to say he’d even like the 32-year-old her? Even ignoring the prison thing, this would be unlikely to work out. Both because they’ve likely become different people over the last decade, and because she clearly has an idealized version of him in her head which she got from the few months she knew him.

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  • honeybeenicki October 13, 2015, 1:22 pm

    WTF is this loveaprisoner website?? Is it a dating website to get matched with prisoners? I don’t understand why this is even a thing.

    Also – don’t contact this guy. If he wanted to be in touch with you, he would find a way. He’s served a lot of time – he’s not going to be the same person coming out. And coming back into society after that kind of time is going to be a really rough and difficult adjustment which would be made much more difficult if he was also trying to focus on being who you seem to want him to be.

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  • redessa October 13, 2015, 1:28 pm

    I agree with everyone else that this has disaster written all over it. What I don’t get is why several people are jumping on her for saying she “just happened” across his profile? The letter doesn’t say that. It says she was thinking of him and found his profile. I took that to mean she went looking for it. I mean, of course she did – we all know that, but I don’t think she’s trying to act like she wasn’t. The bigger question is why? LW, figure out what’s so amiss in your life that you feel the need to seek out prisoner you barely know in order to connect with someone.

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  • snoopy128 October 13, 2015, 1:41 pm

    Can we also just take a pause and think that maybe *he* doesn’t want to get back in touch with her? I mean he wrote her a letter and she never responded. I wouldn’t be too keen to rekindle a friendship or romance with someone who never reached out or responded while I was in jail. I could understand why they may not respond, but they wouldn’t be at the top of my “people to get in touch with once I’m out” list, especially because that transition time can be so hard.

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    • SasLinna October 13, 2015, 1:46 pm

      Yeah, this would be the default assumption actually. Typically I don’t want to hear from people who deliberately ceased contact with me at some point 11 years later.

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  • Married by Elvis October 13, 2015, 2:41 pm

    Can I just say that Wendy has some of the very best, click-baiting headlines? This one was pretty good, but it will be very hard to beat “He bought another woman socks.”

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  • Diablo October 13, 2015, 3:02 pm

    Armed robbery. Lengthy incarceration. Decade with no contact. Is there seriously no such thing as a dealbreaker anymore? What are you thinking? “He’s Just Not THAT Into Prison?” Couldn’t you just find any poor soul lying in a gutter, wash him off, and be looking at someone better than Mr. Ten (Without Parole)?

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    • Just Max October 13, 2015, 3:08 pm

      This made my day. Thank you!

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    • othy October 13, 2015, 3:32 pm

      “It was only a little gun”
      “He didn’t really mean to rob them”
      “His friends talked him into it”
      “He really is that good in bed”

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  • anon October 13, 2015, 3:41 pm

    In the LW defense, may be she dated even worse losers that a ex-con is looking better in comparison 🙂
    – a girlfriend beater
    – a constant cheater
    – a meth addict

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    • Stonegypsy October 13, 2015, 3:48 pm

      Hey! rub-a-dub, ho! rub-a-dub, three maids in a tub, And who do you think were there? A girlfriend beater, a constant cheater, a meth addict, and wow this rhyme totally fell apart.

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    • Cleopatra Jones October 13, 2015, 4:01 pm

      Yeah, I was just thinking what kind of guys she’s dated in the past 11 years that make an about-to-be-released-convicted-felon, a prize winning catch? A guy that she dated for all of 2 or 3 months.
      I mean, sure if he’s Jeremy Meeks, I can see trying to holla at that but even then I wouldn’t try to build a life with him.

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    • Miss MJ October 13, 2015, 4:08 pm

      If an ex-con she knew for a couple of months 11 years ago is better than anyone she’s dated since, then it is beyond time for a dating break. Yikes!

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    • anonymousse October 13, 2015, 4:20 pm

      I still think the incarcerated violent criminal who has been in prison over a decade sounds a lot worse.

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    • ron October 13, 2015, 4:57 pm

      The aim higher applies to your three hypotheticals as well as the convicted armed robber. Over ten years for armed robbery around here would mean he either had prior convictions or else this was a rather nasty armed robbery. There simply is no dating history which makes chasing after this felon a reasonable option.

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  • bittergaymark October 13, 2015, 5:50 pm

    I say… go for it. Look, if your judgement IS this fucking whacked — hey, lets face it… You’re so not ever going to do any better.

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