Theoretically, Dick should have figured that Damian wouldn't want to go to bed.

Okay, back tracking a bit, Damian was regressed, Dick was the one home at the moment, and happy to be looking after his regressed younger brother.

However he may not have accounted for the fact that Damian, would not want to go to bed. The boy already didn't when he wasn't regressed, Dick admittedly should have seen that coming.

So there they both sat, one waiting for the other to break first, as much as Dick would like to give into his little brother's demands, he shouldn't, Damian still needed sleep, as did Dick.

Damian laid in bed but refused to fall asleep, a plush bat stuffie snuggled in his arms.

"C'mon Dami, you can't stay up forever, why not just go to bed, won't you feel better after?"

Dick tried sweet talking the boy into sleeping.