I don’t necessarily believe that Dexter wishes he’d never dated or met Carina, but I do think he wishes he could have seen who she really was from the beginning. He was so incredibly blinded when it came to her and that’s what destroyed him. Dexter believes his experience with Carina opened his eyes a lot more and allowed him to be much more cautious of relationships and even people in general. It was a terrible situation all around but he doesn’t regret being with her.
As of right now, Josie doesn’t mind Dexter’s career choice too much. Of course she worries about him getting in trouble with the law but Josie has always allowed Dexter to do what makes him happy. We’ll see how her feelings change when Dexter ‘advances’ in his career, though. 😉
Thank you for this ask, I actually really enjoy answering asks about my OC’s like this so if anyone else has any questions about my story, feel free to send them in! :D<3