The Sexist

Dating Advice for the Recently Incarcerated

A recent query on the anonymous relationship advice messageboard on LipstickAlley:

How soon after Man is released from Prison do you date him?

Let's say you meet a man tall, attractive, no kids, and then he drops the bomb I have been in jail for the last ten years and just got out 8 months ago. What do you do? Would you immediately stop talking? Would you be curious about if he had sex with another man? Is him being released so recently an issue?

Would anyone date a man just freed from prison?

But after receiving a few dozen variations on "never"—such as "Only if the Father, Son, Holy Spirit and a host of angelic beings repeatedly told me to do so in a 3 dimensional vision on a Bose sound system"—the questioner assumes a new problem. It isn't the possibly-violent-criminal thing or the curiosity-over-the-gay-sex-thing—it's the "chemistry" thing:

I actually was going to tell him to stop calling me because even though he's a nice guy and he seems to like me a lot, I don't feel the chemistry. Then before i even said that he told me about he just got out. He just told me and I didn't say anything, he just kept talking. When I met him, I just thought, wow, a nice, older, quiet man with no kids? (i'm in my 20s, he's in his 30s)

now if i tell him to stop calling, he will think it's because he just told me that he got out of prison.

While LipstickAlley was quick with a response to the "Should I date a former inmate?" query (answer: hell to the no), the more difficult question—"How do I stop dating a former inmate?"—was met with silence. I don't know—perhaps this group of anonymous Internet commenters has more experience letting reformed criminals down easy?

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  • Bill

    you ladies are crazy.

    ALL of you.

  • Daniel M. Laenker

    I'm sorry, I'm sure this is the wrong way to go, but I do wonder about the double indemnity of not dating someone just because he or she is an ex-convict. If there are external factors, I can understand that - but how much more punishment do people have to go through for their crimes?

  • Amanda Hess

    Daniel: Yes, there are so many weird assumptions in this post that I'd never been exposed to before:

    a) You can date an ex-convict, as long as he's been on the outside a specified amount of time;

    b) You can date an ex-convict, as long as he never had sex with a man in prison;

    c) You can stop dating an ex-convict, as long as the reason you stop dating him isn't because you found out he was an ex-convict.

  • Mrs. D

    The thread does leave something to be desired for the more egalitarian-minded. What was he convicted of? What were the circumstances? Does he own up to it? Has he changed (for the better)? Was the offense one that may put you or others close to you in danger? Does the commission of the offense violate a moral code, ideology, or belief of yours that is inexcusable?

    Personally, I know people who have spent a good amount of time in prison for really, really dumb things. Like getting high, breaking into a friend's house (to sleep, not steal), that happened to be said friend's parents' house, but friend wasn't there, and parents freaked, and oops, before the silliness was realized, the cops found the remainder of the drugs on him...uh-oh...major prison time, even though the parents wished to drop the charges after the mess was sorted out (and please don't pretend that you've never been so high/drunk that you've done something stupid, maybe not that stupid, but stupid nonetheless). Also, simpler cases where it was just people who had drugs on them, but it was like 1/10 of a gram over the "distribution" threshold even though there was no evidence whatsoever of distribution. Especially given the war on drugs, a number of otherwise good people end up spending time in prison for stupid, stupid offenses.

    Then again, I perused the website last night, and most of it seemed to be silly, shallow, one-dimensional questions AND answers. I guess it goes along well with our silly, shallow, one-dimensional society.

  • Sherri

    I'm dating an ex-con....He was locked up for 2 yrs for drug trafficking. NO he NEVER slept with a man EVER! He does have a little girl who he hasn't seen in 8 yrs. The mother moved away and wouldn't tell his family where she was to keep him away. He owes a lot of child support! Can't get a decent job, because he's an ex-con... Doesn't have a driver's license, because he's an ex-con, and won't for 2 yrs!! I found all this out after dating him for over a month and started to fall for him... Spoke to his mom quite a bit and he's VERY close to his mom. Met the family, went to his hometown for Thanksgiving! Overall, he's a decent guy! It's the job situation that bothers me, and not being able to drive! I feel like I'm his chauffeur! I have a lot of anger toward him lately because of it... Help! Should I continue to date him? Oh yeah AND he lives with me...

  • zee

    I met a guy who was out of work release from a half-way house. He had been in prison for two years for theft/receipt of stolen property (car parts). Nothing violent. He was and is a very attractive man - tall - dark - handsome. He had a month more in the halfway house and then he was going to be released. I visited him every week- and sometimes twice a week. We talked and had great conversations. He understood what he did was wrong - regardless as to the circumstances. He just got out a few weeks ago and let me tell you - he is very "needy". He has no car - no real job - living with a family member. I am an established professional and find his circumstances matter how much I like him. I have had to "loan" him money just to get him started and I have bought him a few things like clothes. He seems very grateful - but I am now beginning to wonder if he is just "using" me until he gets back on his feet. In any case, I have decided to not answer his calls anymore - and am reluctantly going to walk away from this fiasco. It is just too much work to have a relationship with someone who has nothing to offer and is always in "need". He also has no car - so I am too the "chaufeer". I am in my 40's and his is in his late 30's.

    So...I say...let the man get on his feet...and then see if he wants to be with you. I have learned my lesson...and am probably now out $1000.

  • Sherri

    I COMPLETELY understand! I do love him! He has really contributed to our household...and YES I too have bought him things. Clothes, watches, shoes...but he has bought me a diamond necklace, a promise ring, and shoes as well. I make it tough for him and don't give in to him. I make him be responsible for himself and not me being responsible for him. I think that is what works for us. He NEVER wants to be behind bars again. He understands now that who you associate with makes a big difference in your life. He's still a little uncomfortable around my friends who are doctors, but he's slowly getting use to it.