He might not be aware that he's repeating himself. Our memories can be a bit fuzzy, and he may think it's a new story to share.
It could be that those stories are very important to him. Maybe they represent a significant moment in his life, and he wants to make sure you understand how much it meant to him. So, he keeps retelling it in the hope that you'll fully grasp the significance.
There could be a psychological reason. Telling the same funny stories might be a form of self - affirmation for him. It reminds him of his own resilience and ability to find humor in a tough environment. Also, as time passes, the funny stories become a part of his identity as an Iraq veteran. They are what he can use to represent his time there to others. And every time he tells them, he is also reinforcing his own sense of self and his place in the world, especially in relation to his military past.
It could be that they are trying to be helpful or have a different perspective on the story and want to share it. Or perhaps they are being overly critical without realizing it.
Maybe because certain business models and success stories in Silicon Valley are so appealing and profitable that they keep repeating them. For example, the story of a startup getting huge funding, growing rapidly, and then either getting acquired or going public. It's like a template that many try to follow, so they keep telling that same kind of story to attract investors and talent.
Maybe she is really proud of her pregnancy experience and wants to share it constantly. It could also be that she doesn't realize she has told it many times already.
He might think it's his best one.
Sometimes, people repeat stories because they are seeking validation. By retelling the story, they hope to get the same positive response from you as they did the first time. It could also be that they are trying to emphasize a point or a feeling that was associated with the story, like how much fun they had or how scared they were. So, they keep repeating it to make sure you understand the significance of the event.
He could be trying to teach you a lesson through that story. He thinks it's important and wants to make sure you really understand it, so he keeps repeating it to drive the point home. It's his way of making sure the message gets through to you.
Maybe she just has a limited repertoire of stories. Or perhaps those are her favorite stories and she wants to share them over and over again because they hold special meaning for her.
It could be that they haven't fully moved on and are keeping tabs on you. Or they might just be bored and randomly scrolling through stories, and yours happened to catch their eye.
Maybe they still have some interest in your life or they're just curious.