I am having a similar issue on a new save. I accepted dads offer and chose to skip the first monday and wait till the next to not conflict with the teacher questline*, but the event didn't trigger. I did give dad a gift before that monday so it might have overwritten something?
*(the office job doesnt end till after school is over and if you don't already have the ability to skip class you would just get forced into a game over because the penalties would build while trying to do both at the same time.)