You have to buy the skeleton key( I think that's what it's called) at the tech store at the mall. In order fo you to cuddle with Anna in that room, Josef must leave. where it shows the day of the week is, there will be a pop up mini screen where it will show how many days has past and Anna's love for you. You just have to make the hearts be at 3-4. I don't think it's a bug.