Katrina1072, I certainly also know what it’s like to know someone from a young age, and or/ before addiction took over, and how upsetting, and just outright weird it is to see how people can change.
One thing I wanted to say, though, is don’t ever underestimate the damage a victim/ nice/ “waif” type person can do. Not sure if the term is still used that often, but in the 90s, “waif” typically used for helpless women. And I’ve come to understand that certain behaviors are not gender specific. Just like some women have the potential to be, and are abusive/ violent, some men can be “victim waif” types too.
And it sounds like he’s figured out that playing it up hits the sympathy buttons and “works”, at least to a certain extent, on you. And even if he never steals from you, and figures out other ways to get money from you (ways that “work” on you), is that really any great boundary accomplishment, knowing he has stolen from others? Look at how he’s treated others. Would setting boundaries around that, knowing he treats other people like crap, really make you feel better? And then he plays “nice” victim guy and he coasts through consequences? These types of people do plenty of damage too.
We all have a story, whether it be child abuse or some other hardship, and it sounds like this in part has been his sympathy ticket. Just wanted to mention that, I know/ have known these type of people too, and a person has to be very careful not to let the victim/ nice guy stuff screw you out of your good judgment, what he’s doing is damaging too. Maybe there won’t be some great big blow up or violent incident, but he can easily nickel and dime, and apologize his way through ruining you life. Death by 1000 cuts, you know?