I've read that dogs like having a routine, but I do think Ollie may be a little OCD. When he gets into a routine, everything needs to be just so. He won't play on his tower of pillows until the bathroom light is on. And among his latest is his nighttime routine.
He'll be sleeping on the couch until I tell him it's bed time ("nene time") and then he'll go to the bedroom and either wait at the bottom of the stairs or the foot of the bed. And he will sit and wait until someone gets in bed and says "ok!" then he'll come and curl up on your legs.
It's pretty funny.