Long story short I am dating someone who is on parole. There has been this girl who has been popping in and out figuratively in his life recently and my bf would tell me she was just obsessed and couldn’t grasp that I’m with him and not her. Turns out this girl was a GUARD in his prison for half of his time in there. She and him had a fling when he got out for a few months and she even helped him finance his bike. I am so blindsided. I understand it’s his past but this was hidden from me and I feel so stupid. Any words of wisdom would be appreciated.

24 comments

  1. Speak with him about it and see how he feels about her. Perhaps he was just ashamed that he had a fling with her. They probably had to keep it hush hush because of how they met.

    Maybe if she financed his bike, perhaps he used her for that.

    Just have an open honest conversation about it. Approach him in an understanding way. 🙂

  2. I think that you must know that this is a huge red flag. I personally would have an extremely difficult time. It’s not the fact that it’s in the past it is the fact that disclosure regarding female friends and past relationships with them is of utmost importance in any relationship assuming that he is attracted to women. If it was early in my relationship it might not cause me to completely abandon it but any other falsehood in this area would probably make me completely reevaluate the idea of having a relationship with this person. There’s nothing to make you crazy like a female friend that is firing your intuition and being told that you’re imagining a connection. Most people have seen their significant other have a connection with someone else and it is torture/ sadism to put someone through that.

  3. I’m a little confused – did you not know he was on parole/had been in prison, or did you not know that this girl was the guard? Or both?

    Also, was their fling when you two were together, or before that? Sounded like before, but just checking.

    I think he should have been upfront about who she is. That being said, I’m side-eyeing her because it’s very inappropriate for a prison guard to be having a relationship with someone who was formerly incarcerated in the same correctional institution. Did anything sexual or romantic happen between them while he was still incarcerated there? If so, that’s really concerning.

    Do you think the reason he didn’t tell you is because he feels shame about the specific nature of their relationship?

  4. I knew he went to prison. It was the guard situation I had no idea about. I hadn’t asked if they did anything while he was incarcerated. The thought is nauseating.

  5. Huge red flag . If he respected you and your relationship he wouldn’t have downplayed it , and he would’ve cut it off . There’s no reason why she should finance anything for him , I have a hard time believing that they’re still not seeing each other . I had a similar situation happen with my ex and I gave him the benefit of the doubt everytime . I ended up finding messages of him and this girl talking about me . he was assuring her that we were nothing , and we were together for 2 1/2 years !!! Moral of the story If something feels off it is don’t ignore that feeling .

  6. It’s not his past if she was still coming around. That makes it the present. He should’ve addressed this and been honest the first time it came up

  9. There is a world where you find peace, calm, stable, strong love. This man is not living in that world. Go out there and find the love you deserve.

  11. i thought it was gonna be a parole officer and was gonna be like, no biggie, probably just embarassed.

    but this is a close relationship with someone he deliberatley kept hidden for a while. pretty shifty, and i personally wouldnt take it.

    though, how did you find out the history of their relationship?

  14. Do you know why he is on parole? This guy is dishonest so I’m wondering if you KNOW why he was on parole, not just what he told you.

  15. Guard inmate romances mostly manipulate the power dynamic and more often than not signal predatory behavior on the guards part. Maybe talk to him about this and realise that he could be the victim here

  17. The guard has broken all the rules by being involved with him and would probably lose her job if her employer found out. If she knows he’s currently seeing someone and she’s still going round to visit him, it doesn’t sound like it’s over. To be honest, I’d get rid of him and be sorely tempted to grass her up as well.

  18. This right here. This is the reason I roll my eyes when we get a post from a 21 year old virgin who laments he will never get a girlfriend.

  22. OP I’m going to be honest You need to dump him and quick for the reasons listed below

    1.There is no way he gets out and they instantly start a fling he was sleeping with her while in prison it’s very common sadly and continued it. So, it already sounds like he’s covering up a few details

    2. Someone doesn’t finance a bike for just a fling because that means she is putting herself at risk for that bike i w and you wouldn’t do that for anyone I would bet my hat that their relationship was and is deeper than he is letting on and he is probably playing you both

    3. i believe he is still using her for financial gains and is probably dating her and the only reason he told you because she was getting suspicious and probably threatened to tell you, so he tells you first his version, so you don’t know the whole truth and when she tells you you’d believe his story.

    OP it honestly sound like he is manipulating both of you her into believing he wants a relationship with her and took advantage of her which is common and is using her for money and who knows what else and he’s manipulating you by making it seem just like a fling when there’s more to it. Please leave OP and next time stay away from people who are on parole there’s a reason people are warned against dating them

  23. Yikes. So he started an affair in prison and used her to get a bike and now she’s still on the radar! Sounds like a winner! Look he lied. Even by not saying anything he’s at fault. You can’t trust him.

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