Getting stuck in analysis paralysis isn't going to help you relate better to this older lady friend. She's lonely, you're lonely. It's okay to talk about whatever you want to talk about but she's not your therapist or guru.
You may need to get away and go to a new city, but not because someone encouraged you to over share, but because you're in a strange neither here nor there relationship with this retired lady and hiding from life and real relationships.
This lady actually is your "armor against equal and real relationships, just like the sugar babies. So you can run but you'll run into the same power struggling.