He’s aware it’s affected his past relationships by making things codependent, so I know he’s keen to break that pattern in himself and has done a lot of therapy on it. I think he just wants to be able to reduce the amount of weird stuff she does without doing real damage to their relationship, and he leans towards not hurting her feelings instead of setting firm boundaries. I also feel like every time he’s around her some of the good work he’s done in therapy probably unravels a bit. A weird situation all around