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Would you date someone who’d been in prison?

258 replies

Fearlesssloth · 08/02/2026 19:57

Sorry for keeping this vague but don’t want it to be too identifying. I’ve been very casually seeing a guy who I met recently through friends. Although I’ve only known him a few months, a number of my friends have know him since school. He got out of prison not that long ago. He was in for quite a few years. Without going into too much detail, his crime has to do with drugs and associating with some dodgy people. There was no violence involved and he was barely an adult when he was convicted. He’s genuinely a lovely guy and it’s clear he has some trauma from his time in prison. It’s clear he’s done his best to get his life back on track, doesn’t do drugs or drink anymore, and is working full-time. I feel a little conflicted about the prison thing though for various reasons. Would you date someone who’d done a long sentence if the crime wasn’t directly violent? And before anyone says this - yes I know he probably indirectly caused a lot of violence through what he was doing at the time but I’m talking about his specific crime

OP posts:
Clearinguptheclutter · 09/02/2026 08:00

Short stretch of prison for a one off thing that was clearly a mistake - maybe

long stretch of prison for something drugs or violence related - no way

rainandshine38 · 09/02/2026 08:01

Nope. Raise your bar love.

LBFseBrom · 09/02/2026 08:04

I have, two fellas when I was young. Their crimes were before I knew them but everyone knew about them and both admitted to me.

One had stolen a car and gone for a joy ride aged 18. He did a short sentence.

The other was done for possession of cannabis and supplying, even though it was only two friends with whom he was sharing at the time he was caught. All three were arrested, only he was charged. He was remanded in prison, his parents wouldn't put up bail, thought he needed to be taught a lesson; when it went to court he was released and given a fine which he paid in instalments.

LazySusannes · 09/02/2026 08:05

I'd say it's too soon for HIM to be dating.

I'm genuinely surprised he's in full time work so soon as he has a record- how did that happen? Did he get support to be placed in a job and has he been honest about his prison record?

It's going to be a bit like a kid in a sweet shop after being in prison for so long. His emotions will be all over the place. He needs time to really focus on his job and living alone before he gets into a relationship.

If he was in prison for a few years, that's serious crime- and was his sentence cut short as well? Often they serve half or less.

If he'd been out for 3- 5 years and had a stable job, a home, etc I'd be more forgiving but it's too soon.

Build5bear · 09/02/2026 08:07

Fearlesssloth · 08/02/2026 20:22

It’s really not about the “dating pool”. I have no problem getting a date. I didn’t end up with this guy because I’m desperate to be with someone or I couldn’t get anyone else! We got to know each other super slow while hanging out with our mutual friends. One of my good friends went to school with him and I’ve known about his existence for many years but never met him in person (because he was in prison). So I’m also not just getting the info about his crime and what kind of person he is just from him, also from our friends who’ve known him a long time. I find your comment a bit sad, that people seem to believe once bad = always bad, and don’t seem to believe in second chances. It’s no wonder ex-cons have such a hard time getting a job and being accepted by society. He regrets his crime massively. I don’t believe people who are a product of their environment & fuck up early in life because of that shouldn’t be given a second chance once they’ve paid for what they did.

Sounds like you have already completely made up your mind and are going to steam ahead anyway so why have you bothered to come on here and ask?

Just a thought, if you want children in the future… Do you really want a “druggie ex-convict” as their father? (Using the sort of language that they will face / be bullied for). Things like that don’t stay secret.

I think you’re being quite selfish, not thinking about the impact on your current / future family because you fancy a bit of rough and the tale as old as time “oh he’s changed”. I’ve heard women say this before and end up in horrific domestic violence situations. Drugs are a violent world and he must have been heavily part of it to get a long stretch.

Also, people change yes, but mostly people stay the same. Or they pretend to change and then revert to form.

Do you ever meet anyone who is really boring, bland and no sense of humour… and then years later they are working the whole room at a party… having everyone in stitches? No. Because people don’t really change.

Whatayear2026 · 09/02/2026 08:08

No. I went out with a guy who had been in prison for a few years in my early 20s. I could never quite get past it and I remember thinking I didn’t want my family to find out.

Everybody loved him. He was someone that people took to and had many friends. However I started to occasionally see an aggressive side to him that scared me eg he confronted a man in a pub once who had been a bit loud with his mates. Nothing to do with us but he went over and threatened him out of the blue. Another time he got angry with me in the middle of the night when we were on holiday and he was kicking walls and doors. I finished it when we got home.

I arranged to meet him once after about fifteen years and he was scruffy and chain smoked weed in my house. He talked about cocaine like he was obsessed. He had labouring jobs but never settled. He wanted us to try again but I told him I didn’t like the drugs. I was actually shocked at how he had turned out tbh. He is still the same now at 60.

I could never quite trust him so that is the main reason I didn’t stay with him and looking back I know I did the right thing.

I think it probably does depend on the crime and the sentence but I wouldn’t personally go there.

cheercaptain · 09/02/2026 08:11

No

Whatayear2026 · 09/02/2026 08:11

The knowing each other’s friends gives you a false sense of security as I had that in my situation as he was very popular but they were not in a relationship with him.

LazySusannes · 09/02/2026 08:11

I don't agree that people can't change how they live @Build5bear . BUT it's too soon.

I'm wondering how he's got a job after being inside for so long and if he's been honest with his employer- and if it's 'real work' and not some rehabilitation scheme created for him.

Being in prison for years (with maybe a reduced sentence and being released earlier) would mean he'd had countless offences, not just one.

I agree that the OP doesn't appear to want to listen to anything negative about this.

But for me, I'd only consider someone like him if his past was years behind, not just within months of being released.

Comtesse · 09/02/2026 08:12

No, absolutely not.

Rosepinky · 09/02/2026 08:13

Uptownfonk · 09/02/2026 07:54

Well, the most obvious answer is because the writing-off of people who have been to prison doesn't just extend to having a partner, does it? I'm sure you can use your imagination to apply it to almost any other area of their lives.

As someone has already pointed out who you date and who you choose to recruit are utterly different matters.

I can and will reject men for all manner of reasons. I might even be friends with someone with a criminal record but when it comes to who I share my life and bed with it’s a very separate matter.

However if I’m in charge of hiring, I will adhere to equal opportunities and fair recruitment practices. So that means unless someone isn’t allowed to hold a certain position (working with vulnerable people etc) due to their offences not being spent, I don’t believe in holding that against them.

BiteSizeByzantine · 09/02/2026 08:30

Him turning his life around will come at the cost of a lot of unpaid labour from you. Pick a better partner for yourself, why start at the bottom rung of the ladder before you've even begun? Apart from ignoring his victims because you like him, how is he going to do in today's job market with a conviction? Put yourself first here, its a long life.

PeachySmile2 · 09/02/2026 08:33

Absolutely not. I am a stickler for the rules, so anyone that’s been to prison is not my type of person.

TheOpalReader · 09/02/2026 08:33

It would be a tough one for me. I wouldn't write him off but I'd be wary if he's not long been out of prison especially if he's been inside for some time. It's a huge adjustment and if want him to be able to be self sufficient and stable before ever going near him.

Also I have family members who have dated people with drug dealing/using habits and it's so easy for them to slip back into the lifestyle when they're stressed, skint etc.

It would also depend on what I'd want out of it, would it be harder to get a mortgage with a criminal record? That sort of thing.

TheGoddessFrigg · 09/02/2026 08:39

Uptownfonk · 09/02/2026 07:54

Well, the most obvious answer is because the writing-off of people who have been to prison doesn't just extend to having a partner, does it? I'm sure you can use your imagination to apply it to almost any other area of their lives.

Women can say No to any partner for any reason whatsoever. We are not rehabilitation centres for damaged men. I would have no problem working alongside someone who had been to prison- and I have, in fact.

But intimate relationships? No. There was a horrible case near me where a woman had felt sorry for this guy recently out of prison. They had known each other at school. She went round his house for the first time and he killed her

99pwithaflake · 09/02/2026 08:40

Absolutely no way.

mindutopia · 09/02/2026 08:44

No.

VimesandhisCardboardBoots · 09/02/2026 08:46

Fearlesssloth · 08/02/2026 20:22

It’s really not about the “dating pool”. I have no problem getting a date. I didn’t end up with this guy because I’m desperate to be with someone or I couldn’t get anyone else! We got to know each other super slow while hanging out with our mutual friends. One of my good friends went to school with him and I’ve known about his existence for many years but never met him in person (because he was in prison). So I’m also not just getting the info about his crime and what kind of person he is just from him, also from our friends who’ve known him a long time. I find your comment a bit sad, that people seem to believe once bad = always bad, and don’t seem to believe in second chances. It’s no wonder ex-cons have such a hard time getting a job and being accepted by society. He regrets his crime massively. I don’t believe people who are a product of their environment & fuck up early in life because of that shouldn’t be given a second chance once they’ve paid for what they did.

It's not about "once bad = always bad" though. It's about minimising your own risk.

Even if he's completely reformed, why bring such a potentially difficult situation into your life when it's so easy to avoid?

RawBloomers · 09/02/2026 08:53

Uptownfonk · 08/02/2026 21:31

I'm genuinely surprised by how many people are just saying no, without much to go on. Some people are shit people, absolutely - but some people aren't, make bad choices and pay a price for it. The deciding factor between good person and bad person is not a prison sentence alone.

By writing off anyone who's served prison time then any sentence surely is a life one. I don't agree with that.

There isn't any one single thing that makes one person good and another bad. But someone who has recently spent times behind bars is at significantly more risk than the average man of being a poor choice for an intimate partner.

FlorenceAndTheSewingMachine · 09/02/2026 08:56

I married a lovely man who happened to of been in and out of prison between the ages of 14-21, he says it made him so he is as he learnt by his mistakes, he has been a brilliant husband and he got better at being a dad, he had no role models growing up. His parents were abusive and when they divorced neither wanted him. He ended up living with his alcoholic dad, he was left to his own devices and got bored and started hanging out with older kids who took advantage of him. It spiralled and it was always him that got caught and he protected those "friends"
We have been married 30+ years, it's not always been roses but it was just a normal marriage.
We ran a very successful business and he has raised thousands for charities and he is my best friend, if they want to change they will buy you got to think of outside influences like their old circle of friends, what would happen if they lost their job? Or got ill?
You do need a serious chat with this man, but communication is key in all relationships.

TwoeightTwoeightTwoOhhhh · 09/02/2026 08:56

I would say no.
Even if he is a lovely man now and has turned his life around you’ll be dealing with the fall out from his youth for the rest of time.
Are his employment options limited now?
Are his family relationships damaged?
Is his mental health damaged?
Is his self esteem damaged?
Does he still know the old crowd?
Has he met a new crowd in prison?
etc etc
None of these are yours to fix but have a habit of damaging relationships over time, and just generally making life harder. If you have the option to choose an easier path through life then take it

watchingthishtread · 09/02/2026 08:58

If he's not long out then he hasn't had time to turn things around in any sort of long term way. It's too soon for a relationship. He has too much baggage. It's a no from me.

Iamnotalemming · 09/02/2026 09:01

Personally I could not. I would not want or be able to deal with the baggage.

HoppityBun · 09/02/2026 09:03

It depends what they were in prison for. If they were imprisoned because of peacefully protesting against some of the many inhumanities that are current, or protesting against the curtailing of rights to peaceful protest, then yes, absolutely I would.

Clarissaclaire · 09/02/2026 09:06

I know a couple, John and Sue, not their real names. He did time for his part in a violent fight when he was 18, the other guy came off rather badly. Sue started dating John after he got out, very much against family and friends’ advice. However everyone now agrees Sue has been the making of him, he has never been in trouble again. They have now been married for many years, have two grown up daughters and are very happy.