Personally I think Honey and Joseph Sugarmen take the cake for this one. I mean the poor lady was manipulated into getting a lobotomy for crying out loud (before you tell me about how times were different back then blah blah blah, I’m well aware,this is just what I think).
Close second would be Sarah Lynn and Bojack for obvious reasons.
Vincent Adultman and his son seem to have a terrible relationship. They can’t even be in the same room together.