Ok, it's too soon for that hint (about bumping into Ashley) to appear. The current hint Ashley is showing now is "The other evening, when I walked passed Mom's room, it sounded like she and Ashley were arguing about something."
So what you will need to do is change the time to 22:00 and go to the foyer as if you're going to Claire's bedroom.
Keep progressing a bit more with Sophia (helping her with her workouts at the health club and going to the sauna immediately afterwards) and Ashley and you should see the hint about bumping into Ashley real soon.