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.