I would not do it, far too many things can go wrong where organized crime is concerned and you could find yourself in a very dangerous, and possibly illegal situation. He may be a good guy, but that certainly does not mean that the people he is involved with are, and from what you're saying I would assume that they are not. I will not go into the morality of it, as that is for you to decide.
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Have you ever watched "Orange is the New Black" on Netflix? if not.....may I suggest that you do.
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I would only consider dating this guy if he retired and neatly extricated himself from his profession. If he resigned and was neatly able to quit with no repercussions and find simple, legit employment elsewhere then maybe you could plan a future with him if you thought he was right for you. But as it stands I would say no. You probably don't know all the gory details and let's be honest, you probably don't want to even think about what he does day in and day out. Is he a debt collector or something? Even if he is a kind, decent person deep down, the people he has to work with and deal with on a daily basis might not be the same.
if you really really want a future with him I would gently try to put pressure on him to move into a different line of work. Its not easy in this case but its possible. But only discuss him changing jobs if its safe to do so. He probably isn't violent in general but still you can't be too sure.
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Posts: 1,725
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Joined: Jun 2012
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I forgot to post.
Your posts convinced me what i already knew.
I declined his offer.
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I think you made the healthier choice... ;-)
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