Even though Tim is a full adult who is fully capable of making his own decisions and choices (most of which are extremely questionable tho), he truly enjoys sneaking out of his fathers house.
Bruce knows, of course? He has...strange methods of tracking all his children. He's very nosy.
Normally, Tim tells Bruce where he's going. Sometimes he calls or texts- "library" or "helping Dick." And sometimes he goes out of his way to find Bruce wherever he is in the manor (normally his office or in the library) knowing it gives his father peace of mind.
But when Jason started inviting him out at night, to go dancing, or hang out with people Tim can actually stand and he knows Bruce wouldn't approve. He is in line for Bruce's empire after all, the press would have a field day if he got caught doing the things he did/wearing the things he wore to the IceBerg Lounge or the CatTail Club deep in the city.
So most nights he sneaks out his window and meets Jason at the end of the manor driveway. And most nights he sneaks back in with no issue. (Most...more to come on that?)
Bruce always frowns a little more than normal the following day while they have breakfast. Knowing exactly what Tim's red eyes and sleepy silence is from.
Bruce knows about the strange thrill Tim gets when he sneaks out of the house or dates the son of his father's enemy. He knows Tim enjoys testing him, seeing how many buttons he can push until Bruce simply wilts or explodes.
And even then, if one day he snapped at his son and his... behaviors, Tim would only give him a wide smile, a sign he'd gotten what he'd wanted all along.
Yea just anyway, Tim keeps sneaking out and Bruce keeps on letting him. Incoherent thoughts after the world's longest writing break.

















