I think maybe this happens in waves? I’ve been with my SO a while, over a decade at least, so we’ve run through the backlog of stories. But there’s usually at least one or two new things to talk about from our independent lives. I guess if we were both retired, we would probably spend less time apart, and have less time to accumulate stories the other didn’t know about.
Although sometimes we just play the crossword, taking turns on one of our phones, when waiting for the waiter.