civilian tim au where he ends up being close-ish friends with the waynes (being one of the few non-corrupt rich folk) but every conversation ends up with him Desperately trying not to let them know that he knows. like / socialite: oh, cass darling! how'd you break your arm? // cass: skiing. // tim, who knows Damn well poison ivy broke batgirl's arm last night bc He Was There: haha what a life you live cass anyways-
AU where Tim has known who the Batfam are the whole goddamn time and pretends all his life not to know.
And the family all love Tim and will only go to the galas and shit if he's there because he's Nice and Sincere and seems to always give good advice as an observant third party. And if they ever need a favor or whatever from him he's all "No problem!" Doesn't ask too many questions. Gives them the benefit of the doubt. Just a true friend. One time Cass said "cause a scene" and Tim didn't even ask why, he just comically tripped and knocked over the nearest ten foot ice sculpture.
So of course the batfam all secretly want him to know the truth. Like, yeah. It's against the rules but Tim is their friend! He deserves the truth! He's so trusting and honest with them and it makes them feel so guilty. Like everytime someone cancels lunch plans w/ him cuz of crime, he's always so cool and understanding?? And they all feel so bad lying over and over to poor Tim who just naively believes them
So then individually all the batfam have the idea to "accidentally" let it slip who they really are.
One time Dick got "caught" wearing his Nightwing outfit and Tim was just like "Holy shit! Nice outfit! Way better than my Halloween costume" "Halloween? Tim, it's August." "Right? So cool that you're into it enough you'd plan so far ahead" "uh. Yeah. Okay. Halloween. Sure"
Damian is at a gala when he curses and walks off to the bathroom, dragging Tim along with him, telling him he needs help resowing his stitches
Damian's shoulder has a bite mark taken out of it courtesy of killer croc. Damian tries to explain, come clean about why he has this horrible wound,
"Drake. I'm sure you must be wondering why I have-"
"Oh, no. No need to explain. I know you love animals. And if you happened to break into the Gotham zoo to try and free the alligators and accidentally got bitten? Well, I'm sure Bruce doesn't need to know"
"...yes. that is... exactly what happened. Truly, Drake, your detective skills are adequate. Even impressive"
"Don't go all sappy on me here, Damian"