I want to cry every time I read this. I feel so bad for Damian. He’s just a child and he’s trying so hard.
Anyway, I give Dick credit here for how he handles it. It would be easy to yell at Tim, but that might drive Tim further away. He gently lets Tim know he disapproves and that this is not necessarily a good plan (as Bruce’s experience shows).
Plus, Tim learns a bit more about Damian, and will perhaps start to understand him better. Damian’s a real person with real feelings, not just a mini-assassin automaton.