he tells me the same stories

You could politely interrupt him and say you've heard it before. Then ask him if he has any new stories.

It could be that he really likes those stories and thinks you might not have fully grasped them the first time. So he tells them again. He might also be forgetful and not realize he has already told you those stories.

You could gently let him know that you've heard those stories before. Maybe say something like 'Honey, I love hearing about your experiences, but I've already heard this one a few times.' He might not even realize he's repeating himself.

You could also be honest and tell them that you've heard the story before. Maybe say something like 'I really enjoy your stories, but I think you've told this one already. Do you have a new one?' It might seem a bit direct, but it can be effective if done kindly.

You could try changing the topic politely when they start. For example, say something like 'Hey, let's talk about something new today!'

They might have a limited set of experiences that they find really significant. For them, these stories are the most important things to share.

Olaf is that cute snowman. He might tell Disney stories related to the Frozen universe. He could be talking about how the sisters Elsa and Anna overcame difficulties, like Elsa learning to control her powers. His stories would likely be full of fun and humor, as he has a very positive and naïve personality. Maybe he tells tales of the enchanted forest and the secrets it holds too.

It might refer to Plato's role as a philosopher who shared profound and influential ideas through his writings and teachings.

He could be a father. Fathers often tell stories to their children at bedtime.

It depends. If she is comfortable sharing and you are a trusted friend or family member, it can be appropriate. It shows that she trusts you.