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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:
LadyLaundry · 09/02/2026 09:07

Please be v careful.
Courts don't send people to prison unless they absolutely have to, and this person was evidently sentenced by a Crown Court as you say he'd been in custody for drugs quite a few years. This is a significant sentence, we're not talking a bit of cannabis.

So lets put that all together and be less vague: you're eyeing up an ex drug dealer and minimising this by claiming he's not violent. That's a bit like considering eating a bag of marshmallows and saying "Well, at least they're fat free...".

If his past gives you the fanny gallops, then nothing will stop you but a couple more things spring to mind:

  1. He's not going to tell you if he's been directly violent, for a start. You actually know nothing about this guy without police disclosure. Nothing.
  2. He has a grey past and now a grey future. Not sure why you'd knowingly pick that.

Huge risk. Suggest picking one of plenty of "bad boy" binges available on a streaming service and a new gadget for your goody drawer.

LadyLaundry · 09/02/2026 09:07

Please be v careful.
Courts don't send people to prison unless they absolutely have to, and this person was evidently sentenced by a Crown Court as you say he'd been in custody for drugs quite a few years. This is a significant sentence, we're not talking a bit of cannabis.

So lets put that all together and be less vague: you're eyeing up an ex drug dealer and minimising this by claiming he's not violent. That's a bit like considering eating a bag of marshmallows and saying "Well, at least they're fat free...".

If his past gives you the fanny gallops, then nothing will stop you but a couple more things spring to mind:

  1. He's not going to tell you if he's been directly violent, for a start. You actually know nothing about this guy without police disclosure. Nothing.
  2. He has a grey past and now a grey future. Not sure why you'd knowingly pick that.

Huge risk. Suggest picking one of plenty of "bad boy" binges available on a streaming service and a new gadget for your goody drawer.

Rosepinky · 09/02/2026 09:15

TheGoddessFrigg · 09/02/2026 08:39

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

Awful story. Poor woman. She paid a hefty price for trying to be kind.

That reminds me when I was 19 and way
more naive/overly trusting I did have a friend from church who had did a stint in jail. Not sure how long but less than 5 years I think.

When I went round to his house alone (not wise!) for a coffee one afternoon, he started telling me more things about himself and I could see he had yet to deal with the anger issues. And he had this mental health episode right there and then where long story short - he thought God was telling us to both take of our clothes.

I thought it was game over for me but thankfully I managed to snap him out of it and got out his flat alive that day and keep all my clothes on!

This man was well groomed, well spoken, sociable, was volunteering , studying part time, and I felt safe around him partly because we attended the same church, but yet he was still very dangerous.

Obviously the issue there was more mental health, but I’m fairly sure the rate of mental health must be sky high among young men in prison so there is a link. If they don’t have mental health issues before going in there they will often develop them as a result of imprisonment.

I learnt a valuable lesson that day and now I don’t hesitate to “judge” high risk men.

LizzieW1969 · 09/02/2026 09:16

It would be a no from me, too, though I wouldn't have an issue with being friends with him if I liked him. Maybe if the crime happened way in his past and he really had turned his life around.

It's all hypothetical, as I'm married and, if that were to change I would still be an adoptive Mum to 2 vulnerable adopted DDs.

canisquaeso · 09/02/2026 09:16

It would depend on the reasons, the circumstances (ie I would understand someone from a difficult background getting involved with drug trafficking but not a privileged person who has no reason other than a thrill), how long they’ve been out, etc.

Build5bear · 09/02/2026 09:19

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.

I know what you mean. A lad I went to school with was heavily involved in gang life / crime and after coming out of prison opened up a boxing school to help young lads and he goes into schools to talk about the danger of knives etc. He’s lovely. Would I have a relationship and kids with him? No.

Like you say, it’s too early to tell. OP’s bloke hasn’t had a clean rap sheet for 30 years after teenage mistakes and she’s wondering about a relationship with him. He literally just got out of prison. She’s got the blinkers on and doesn’t want to hear anything bad. She just hoping for confirmation (maybe to show her real life doubters). Didn’t get it, so she probably won’t be back.

Forty85 · 09/02/2026 09:19

Absolutely not.

allthingsinmoderation · 09/02/2026 09:21

How did you find out about his criminal past?
Are you sure you know the full facts about his offending?
Could you do a Claires law check ?

CasuallyConfused · 09/02/2026 09:22

Absolutely not. There are millions of other men to date, why would you pick one that has been to prison for drug offences? If he's been involved in this sort of crime and in prison the sorts of friends he keeps aren't going to be great people either. I wouldn't even be associates with someone like this, nevermind date them.

dawngreen · 09/02/2026 09:23

And even dealers have drug habits. They say its just a bit of cannabis. But a lot end up needing the hard stuff just to cope with life.

Lamelie · 09/02/2026 09:25

No. Probably more for future you than now. His record could impact security clearance for future opportunities for you both, like travel, emigration, fostering, business

Parsleyforme · 09/02/2026 09:26

Everyone I know with convictions has become a drug dealer and/or gone back to prison. This is obviously not everyone in the country, but that’s my personal experience. The latest guy (friend’s boyfriend) seems like he wouldn’t say boo to a goose but went to prison young, recently lost his trade apprenticeship because he was arrested again, and his drug dealing has escalated into rivalry/violence. So much for “hanging around with the wrong people” before he was first locked up

Fearlesssloth · 09/02/2026 09:29

VimesandhisCardboardBoots · 09/02/2026 08:46

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?

I’m sure you’re grown enough to know that relationships, who you’re attracted to, and who you fall for are far more complicated than that.

OP posts:
icebearforpresident · 09/02/2026 09:34

It’s all hypothetical as I have been with my husband over 20 years at this point but I wouldn’t say outright no. I wouldn’t start dating someone who was released last week but similar circumstances to the OP that happened a number of years ago involving a non-violent crime with no reoffending? I wouldn’t say no just because of the time in prison.

ClawsandEffect · 09/02/2026 09:34

In two minds.

A friend has an absolutely wonderful husband who was in jail as a teenager. He really is the model husband now.

However, another friend, desperate for a family, has hitched up with an ex criminal and he is a nightmare. Can only earn minimum wage, and is highly resentful of this fact. Has been over indulged by his mother, despite his jail time, which has resulted in a fracture in his relationship with his siblings. He is causing problems with his partner. She caught him chatting up a mutual friend and decided to blame the woman, rather than him. She's now 2 children in with him (1 is a baby) and he's still clearly not happy despite both of their families trying to help them stay afloat financially. So much so my friend has arranged relationship counselling for them to try to fix his discontent.

I can see him going back to crime because he clearly believes he deserves more than he has, despite having a good life handed to him on a platter (e.g. not worked for or earned by him). I can't imagine what my friend saw in him. She's 41 though and I think her body clock was ringing very loudly.

If I were her, I'd bin him. But equally, I would never have considered him in the first place. His crime wasn't a minor one.

MylipstickiscalledHugMe · 09/02/2026 09:35

This is a mad question. Not all men deserve a woman.

There are so many to choose from! Also being single can be quite nice - more freedom, more control over your life, less mess :) etc

Neurodiversemom · 09/02/2026 09:36

A big Fat NO.

dottiedodah · 09/02/2026 09:39

I think he sounds nice on the face of it ,and you get on well which is good .However it much depends on the length of his sentence and why he was in.Do you have DC or do you want them in the future? How will he cope as a Dad with a messed up youth do you think . There are more questions than answers here .Long prison sentences arent given out like Smarties . He must have done some serious shit .How old is he ,and how does he feel about life in prison .has he come to terms with it or does he feel bitter about his wasted years? I would probably pass TBH.

Lamelie · 09/02/2026 09:39

@Fearlesssloth “I’m sure you’re grown enough to know that relationships, who you’re attracted to, and who you fall for are far more complicated than that.”
I you were my friend I’d roll my eyes at that.
You have agency. You, NOW, can choose whether to hand over a lot of your life choices and events to someone else or retain control. If you marry or have children with him you’re ceding a lot of power. I’m not sure any man is worth that.

Cankerousa · 09/02/2026 09:39

Never.

Prison isn't something a good man accidentally stumbles in to. And these days especially it takes serious or sustained criminal effort to get in there.

IngridBergmannn · 09/02/2026 09:42

I did, in my very early 20s. Well when I met him, I didn't know what he did for a living, we met at a club, started dating afterwards. He might not have been in prison up to that point, this I also don't know (it's not like he would have told me), but he was a drug dealer. Not just that, but some sort of a kingpin, not just a regular dealer. Obviously, when I met him I didn't know any of that.

Long story short, he ended up in prison and is doing a 20 year old stint now. Doing the maths, he should be out sometime soon, if he's still alive. I didn't keep any contact.

I must say, he wasn't violent or abusive in any way towards me. But obviously, I'm not kidding myself that his chosen 'occupation' didn't involve violence.

Would I do it again now? Absolutely not. I'm older and wiser than that.

Although my good friend was also in prison. For a non-violent theft, when he was very young. I've known him for more than 20 years now. He never went back, and has been on the straight and narrow since then, has a job, home, etc. Would I date a guy like that? Sure, I don't see why not.

wishingonastar101 · 09/02/2026 09:43

I would certainly find out all the facts. Not just hearsay or his side of the story.

bandog · 09/02/2026 09:48

I wouldn’t but if you are keen to, give it time. There’s no problem socialising in his company and keeping in touch but I wouldn’t date him or get into a relationship until he’s been out at least a year, can show you he’s stable, has kept up all his commitments to probation officer / support worker, has a steady job sorted and is rehabilitating. Things can go well at first but when initial buzz of release wears off and support from family and friends dies down things can look very different and it’s common to slip into old habits, especially if mental health is not great.

GoldenGeishaGirl · 09/02/2026 09:49

You wouldn’t be questioning it here if you genuinely thought getting into a relationship with this man is a good idea. There’s something that’s holding you back and you need to trust your instincts instead of trying to come up with excuses to date him.

FullLondonEye · 09/02/2026 09:53

I'm a bit surprised at the strength of feeling against this one.

My husband was in prison when he was younger (no violence). He was stupid in his late teens, got caught and paid for it. You couldn't find a more law abiding person and productive member of society now. He's always been very clear that he learned his lesson and will never go back. For him the system worked.

While my husband's sentence wasn't that long, in this case you have the advantage that this man isn't a complete stranger to you because you have mutual, long term friends. If they all vouch for him and these are people whose judgement you trust then that's a very strong point in his favour. That would probably swing it for me.

It's a risk definitely but there are an awful lot of men out there who behave very badly in various different ways and don't go to prison because they manage not to get caught. Mumsnet is full of women living miserable lives with them. Arguably you at least know the bad news in this case. He could still be an awful person in other, hidden ways but so could anyone else.