Woman’s Parents Blindside Her Boyfriend At Dinner Over His Prison Past

Meeting your partner’s parents for the first time can be scary. Now, imagine you’re dating someone who has been in prison — and your family starts asking them questions about their past. It’s totally normal for them to be concerned and want to know all about the new person in your life. But is there a right way to delve into this personal and potentially upsetting material?

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One Redditor isn’t sure how to feel after her family joked about her new boyfriend’s past in jail while the two were over for dinner for the first time.

“I (25F) have been dating this guy (33M) for 9 months now. He’s amazing and I’m head over heels for him and he’s the same for me. My boyfriend had a tough past, he had a rough upbringing and spent some time in prison over a decade ago. Once he got out, he turned things around and managed to build a very good life for himself,” the OP says.

“I found out about his past on our third date. I asked him about a small tattoo on his arm, which turned out to be a tattoo of the date he was released from prison. None of that mattered to me because it was in the distant past. I briefly mentioned it to my sister one day and did not go into any details about it. My sister and I have always shared things about the guys we date and I always thought it would stay between us. Or so I thought. On Sunday, I introduced my boyfriend to my parents for the first time. We went over to their house for dinner and everything was going well until my dad brought up at the dinner table the fact that my boyfriend had spent time in jail. It blindsided my boyfriend and I. I did not tell them about it beforehand so I immediately realized it must have been my sister.”

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“My parents proceeded to question him about all that, asking why he was in there and making jokes like ‘it takes a certain someone to go to jail’ and ‘you don’t go to jail for no reason.’ Those things were said in a ‘jokingly’ way but it felt condescending and I’m sure my boyfriend felt it too. We ended up cutting dinner short and I had an individual conversation with my dad and basically told him that what they did wasn’t cool and that I was mad. He kept saying they were joking but it didn’t feel that way.”

“I apologized to my boyfriend on our way home and he just said, “It’s okay babe. It’s to be expected.” He said it in a defeated way which told me that he was hurt. He never said this to me, but I imagine that being judged over one’s past, especially when you’ve built a great life for yourself, must feel awful. I feel so guilty for all of this and although he seems fine, I feel like it affected him more than he wants to tell me. I don’t know what to do. I regret not being more vocal when all of it was happening, I’m not good at confrontations. I’ve been thinking of calling my parents and telling them they need to apologize to him as soon as possible but my sister (who I confronted) says I should let some time pass and make them apologize next time we see each other which is god knows when.”

The OP added that she feels her boyfriend has genuinely tried to improve himself and make strides to have a better life:

“He did time for illegally selling firearms and drugs with his father. He grew up in a very abusive household and his abusive dad had a “business” of selling illegal guns and drugs. The dad got my boyfriend involved at a young age and that’s how he got caught up in it . Long story short, my boyfriend ended up getting a good deal, did time and was already out by the age of 22. Yeah he did bad things, things that a lot of people don’t do but that doesn’t make him a bad person for life and he really turned his life around and is doing very good. I’m not going to judge him for something that happened a long time ago under circumstances that I will never be able to relate or understand because I had a very good upbringing. He just has a lot of baggage which he went to therapy for and the story isn’t black and white.”

What should the OP do?

“I get the feeling that what for you were ‘jokes’ and ‘condescending remarks,’ for them was the least aggressive and friendliest way to find out about their daughter’s current boyfriend, who is 8 years older and spent time in prison. I know that you are blinded by love and you are completely on his side, but the reality is that every father and mother would be more than worried about their daughter if she were dating a man with those two characteristics. Surely, they didn’t want to confront you directly for fear of driving you away and getting closer to him, so the way they devised was through meeting him directly and asking him questions directly, and trying to lighten everything up with jokes. At this point, what you would need to do if you want to continue your relationship with him and your parents, is talk to your parents about his time in prison. YOU, not him, YOU. You’re going to have to confront them, tell them your boyfriend’s story, defend him, and then give them space to process and give them the option to talk directly to him about all of this. Honestly, if neither you nor he is willing to talk about prison time and answer questions, I don’t think the foundation for a relationship between him and your family will ever form. Good luck OP, try to put on your big girl pants and not stay silent in situations that require you to speak,” said


“They shouldn’t have asked him jokingly. They should have asked him seriously. Did you expect your family not to ask your boyfriend why he spent time in prison?” asked


“I have a little bit different opinion. My husband has a shady past – drugs, car theft. In and out of jail for a few years doing a few months at a time. He was convicted of a felony for auto theft and was given a break by a judge and given a suspended sentence. If he had been caught again stealing cars or even tools to steal cars, he would have gone to prison – not jail – for three years. The last time my husband went to jail he actually had an outstanding warrant, he called the cops to come pick him up because he was tired of running, did his time and turned his life around. Stopped stealing cars, procured gainful employment and has just been on the straight and narrow ever since. Anyway, that being said, my husband was open about his past from day 1, even before we were together, so to me, it does raise a little bit of a red flag that OP had to ask before he came clean about his record. I don’t know if OP states what his felony was for, but that’s definitely something I’d want to know beforehand. All of that aside, I would be mortified if my family did that to my husband. I do NOT blame the family for having concerns about the fact that he’s a felon (again, not knowing what his felony was for) and that their daughter is dating him/brought him into the house. But that was a conversation that should have been had after the fact with OP. Shaming someone for their past (and there is always a bit of seriousness behind ‘jokes’ like those) when it’s obvious they are working to be better than they were is not okay. OP, you should have a convo with your family – I do believe they have the right to know what he was convicted of and did time for if he’s dating you, especially if you generally have a good relationship with your family. And truthfully, there are some people that will never look past the felony and they will always hold that against him. But I’d tell your family that jokes like that are hurtful and shameful and that they are not okay,” shared


“If my kids brought home an ex felon (Or If I presented my parents with an ex felon) you better believe he would play 20 questions. I wish your parents had gone about this in a very different way, but my guess is they where pissed and concerned about your choice in partner. Their minds where already made up and they didn’t want to give him a chance. and your sister, though you may view it as a betrayal of your trust, was actually looking out for you by telling your parents something that could be life threatening (if he went away for assault and battery, if he has a history of violence, etc). Now if this person turned their life around and learned their lesson then by all means, tell your parents he did his time and should be judged for the person he is now, not for the mistakes he made when he was younger. we all do dumb things when we are young, some more then others (my dad and his friends spent 2 weeks following patrol cars to learn their routes and then lit every trash can on the beach when they knew the cars would be at their farthest. He said it was glorious, My brother threw rocks at window of a house he thought was abandoned, was not. and I stole food from the groceries where I worked, was never caught but could have been very bad) just remind them that everyone does stupid things, he just happened to get caught. Best of luck, and even though they where asshats for how they dealt with it, please try to remember they did it out of love and concern for you. but yeah, they owe both you and him a big apology and maybe a make up diner,” said


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