Well Olivia showed up that first night after Lisa's and Max's first date.
View attachment 24280
Waiting on the next trigger for the movie.
Lisa's mood was low and after doing dishes and helping with homework without error is why Olivia showed up.
Still have not triggered the movie yet.
ADD: It looks like part of the quest was not triggered in v8 and now in v9 it will not trigger the movie.
All I can say is get all girls mood up as high as they will go and keep playing and it might trigger. Mood = Lisa, Alice and Ann (mom).