Hey Lemy,
Thanks a bunch for the save. I see in this save you're on chapter 9 of Rae's story.
If you go to the attic and then her room, wait until evening, play the scene out with the wine.
Return the following day, head to her room again at evening time, select "talk..." and you should get the option to "Walking the city streets in the night."
That should progress her story!