Another thought
I like the thought of Damian trying to get along with Tim, like, he is the first person to try to stretch out his hand as a peace offering. They may not be “I-want-to-kill-you” phase anymore but that doesn’t mean the tension is gone.
Damian would plan a whole day of what to do or an event or something similar of that sort to hand out with Tim. He’s going to be the person who a) will plan an event through his own interests because brothers would share their interests with each other or b) something that Tim likes. He would be a person who would whole heartly go all out to make sure the day was perfect because the Bat paranoia has to come from somewhere. He would plan everything to what they would do from sectioning their time to tactically make sure his whole family was busy with something else that every day. (He has to bribe either Cass or Duke to get Dick off his back. Alfred already has Bruce covered.)
The thing about Damian of being a perfectionist about the day they hang out is that Damian would expect certain reactions from Tim because it’s a brother-hang-out day that he planned. But Tim would either be very tense, suspicious, bored, or out right in exhausted pain. These are not the sort of reactions he gets when he goes out with Grayson or Brown at all and its slowly driving Damian into a panic because something went wrong with his plan, and he doesn’t know what to do. This confusion leads to Damian letting his emotions out as anger and would either get mad at Tim or be very snippy with Tim throughout the trip.
Meanwhile, Tim is trying to understand Damian’s motive of taking him out and thinks this is just him messing with him or that this is a punishment of sorts.
Both boys do not know how to communicate with each other which leads to high tensions and disasters.
Damian will try to go more planned days out with Tim, but it doesn’t work, and he doesn’t understand what he is doing wrong because “this is how Grayson took him out for the day does he want to be kidnapped like how Todd does it????”
Someone’s going to come and fix this eventually, just let them get it out of their system.
+Cass would help them
+Dick too once he finds out what is going on by a panicked Tim calling him about Damian
+Jason will not want to get involved because this is not for him to intervene and it makes good drama to watch
+Steph see’s it too and is between face palming because of Tim or laughing before hinting at Tim what Damian is trying to do which he flat out does not believe (best detective my ass)
+Duke will not touch from a 100 ft radius but if Tim is complaining during his time then he will make sarcastic remarks which Tim takes the literal opposite way of what they mean
+Barbara is a mix of Duke and Steph, mostly Duke when both brothers do. Not. Take. The. Hint.
+Alfred has Bruce covered, just don’t worry about it much
+But yes Alfred will have tea and coffee at the ready when both boys come to him at different times to complain about each other
No idea if people would do an angst or a crack type of path with this
