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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:
Riverflow6 · 08/02/2026 20:33

Absolutely not in a million years

user1476613140 · 08/02/2026 20:33

No.

TomatoSandwiches · 08/02/2026 20:34

How long did he serve and how long has he been out?

persephonia · 08/02/2026 20:36

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.

I think the second chance should be to show that they can reintegrate into society, not fall back into old habits or back into bad friendships etc. From the sounds of it he hasn't had the chance to do that yet because he hasn't been out for long.
It's really good that he regrets his actions. But at some point he's going to be tested. His friends that got him into drug dealing will pop back. Or people he met in prison will come by.nor he'll struggle to find a job/feel low status in the job he has and think about how much easier he could make money if he dealt a bit on the side. Or he will be on a night out and want to do coke.
That doesn't mean he's doomed to fall back into old ways. But he will need to be capable of facing that himself. You don't want to be the nagging girlfriend fretting about the friends you don't like turning up again while he tries to defend them/argue he just popped round because of a one of thing/he's his mate and he had his back etc.
I would rather stay friends for a long while if you want to keep contact. If you do end up dating him anyway (you sound like you are going to) double up on birth control. You don't want to be pregnant and arguing because he went out last night and didn't come home. Or he's under pressure to make money to provide for the baby so does something stupid. Because at that point you won't be able to just walk away if he's backsliding. There are thousands of women like that in this country right now.

lottiegarbanzo · 08/02/2026 20:37

No.

What should you do though? My advice would be to focus on yourself and your own interests. How does he improve your life? Is that enough? Everything you’d hope for in a relationship? Better than anyone else could offer?

Does he bring any downsides? Are they acceptable or not? Be honest. Do not for one second imagine you can save or change him. You cannot.

Bear in mind opportunity cost. While you’re spending time with him you’re not looking for someone else, someone potentially better for you.

1000StrawberryLollies · 08/02/2026 20:38

No. Why take the risk? There are plenty of men out there who haven't been to prison.

lljkk · 08/02/2026 20:41

I've not been in prison but I've done plenty of life fuck ups.
I would take a relationship like OP describes, one day at a time.
I believe in people reforming and becoming better persons after earlier life mistakes. That this is possible and does happen.

If you can't think that way, then you can't.

happysinglemama · 08/02/2026 20:42

Through experience, my advice is a big no. Don't become a rehab the problems never end

1000StrawberryLollies · 08/02/2026 20:42

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.

Second chances in terms of being friends, being offered jobs, sure. I don't believe in second chances or the benefit of the doubt when it comes to dating. Enough potential partners turn out to be a bad choice even if they don't have any obvious red flags. Choosing one with known red flags seems nuts.

JLou08 · 08/02/2026 20:43

I wouldn't. I believe people can turn their lives around and are deserving of a normal, fulfilled life once they've served their time. I think having the opportunity at that would likely reduce the risk of reoffending, too. I wouldn't take the risk though, I have children and work in a professional role with vulnerable people. It's hard to know if I would do it without those factors to take into account.

Wynter25 · 08/02/2026 20:43

No

Blondeshavemorefun · 08/02/2026 20:46

His old was he when went in

how long was sentence

how long has Been out

what does he do for a job now / if he can find a job

where does he live ?

ImPamDoove · 08/02/2026 20:47

Never in a million years

Dymaxion · 08/02/2026 20:47

Wouldn't be a blanket no, I know someone who went to prison for drug/robbery reasons. He did an incredibly stupid thing, did his time and went back to his old life, the one he had prior to becoming involved with drugs and didn't re-offend.
I would be extremely cautious though, especially if his release was recent.

AngelinaFibres · 08/02/2026 20:48

" Could you lend me some money.....just til I get back on my feet"
" Could I leave something at your house. A mate will pick it up this afternoon "
" Can my mate sleep on your sofa. He can't stay at his house for a bit".
Wake up Op

BlackCat14 · 08/02/2026 20:48

I wonder if it depends what you’re after. How old are you? In my early 20s I was dating and having fun, looking for boyfriends but not necessarily my future husband/father of my kids, back then I don’t think I would have minded so much, if I liked him. But as a woman in my 30s looking to find my forever, I’d be perhaps more dubious.

Maddy70 · 08/02/2026 20:50

It depends why , when and what changed between then and now

ohyesido · 08/02/2026 20:51

No.

TheBlueKoala · 08/02/2026 20:51

If I didn't have children and I was absolutely convinced that he was no more associating with dodgy people then yes, why not if he's lovely, respectful and made me happy.

TippyTee · 08/02/2026 20:52

No.

Starseeking · 08/02/2026 20:53

Personally, no.

I’m an extremely law-abiding person, barely had a parking ticket lol I would feel that our values were completely misaligned.

I also have children, my own home, and a well paid job. I can’t see how anyone recently out of prison would enhance the life I’ve built for myself in any way.

I’d be interested in the housing situation of your new man and if your new man has a job? If not, how is he planning to support himself long-term, and what steps is he taking to get there?

AwayInTheWind · 08/02/2026 20:55

Yeah. Then again, I personally know a few fantastic, wholesome people who’ve been to prison for dodgy shit in their past though. So I’ve seen firsthand how people can grow up and turn their lives around.

Seawolves · 08/02/2026 20:56

No, I am a foster carer and, for me, children come first.

Hellohelga · 08/02/2026 20:57

No. I wouldn’t be attracted to someone whose idea of a good career path was becoming a drug dealer.

TheDogsSmile · 08/02/2026 20:59

No. I know someone who is married to a man who was in prison years ago. Life isn’t simple. People often don’t want to be around them as they judge, work can be hard therefore money issues etc. And I’d never believe someone like that actually changed, not really. Too messy.