and long story short she decides to go out with a drug dealer who is obviously not very good at dealing drugs, has no job to suppliment, and cant drive because he's a dui...
You're dating in a pool of people with very diverse value sets. So I'll give you my take, given that I have a very... iconoclastic... set of values.
Drugs are a product that people want and are willing to pay for. In the biggest case, some of the "illegal" drugs are safer than the legal ones. And yet, they're still criminalized. Despite this criminalization, those transactions are almost always done on a voluntary basis between consenting people.
And you're stigmatizing them. Perhaps that's a turn off to the people that you're dating.
My step-mother dated one-after-another in a string of physically abusive, violent aggressive assholes. What she didn't understand then was that she was attracted to counter-traits of that. She wanted a man who would "take charge" and "be confident" and her example of taking charge was ignoring her wishes if "he thought it was best". This same trait, which I pretty much consider a lack of respect, allowed those same men to smack her around and smash her face into walls when she did something they didn't like.
The only way for her to get out of the "all of the guys around me turn out to be dicks" rut was to honestly evaluate what it was that she was attracted to, and find the common (positive) traits she found in all of the abusers and stay the hell away from them.
Perhaps you're dating "freaky" women. Ladies who are unabashedly sexual, iconoclastic, critical thinkers, thrill-seekers. whatever. The flip side of this is that when they DO think critically and ignore the law, they run into folks who conflict with YOUR value sets (you seem to value law-abiders, the stability of a regular job, et cetera). Until you reconcile those disparities, you won't find someone you connect with on the level you're looking for.