You don't talk to Anna. As far as I'm aware, you have to do the following:
-Witness the Josef/Adrian scene where Adrian finds out he can't go to Japan
-Go to Adrian's room and pick the Adrian Leaving Route option
-Earn the $20000 needed to pay for his trip and give it to him
-Open one of the Sharing Routes (I would recommend Alice, since you can steal her later if you want)
-Keep visiting Adrian until he starts talking about how much Josef and Anna like you more than him, and choose one of the nice options.