One of the great benefits of having friends who are at least twenty years older than oneself is that they have a wealth of life experiences that they are happy to share. This enables one to circumvent the problem in the popular saying:

Good judgment comes from experience and experience comes from bad judgment.

Having significantly older friends means that one can benefit from their experience. (The same is true of parents, if one can bring oneself to listen to them.)

But there is a problem with listening to the stories of people who are several decades one’s senior: they tend to tell you each story several times. Contrary to popular belief, this is not because they’re old, but because while stories are memorable, the act of telling them isn’t. In fact, telling a story is actually quite hard to remember because the storyteller’s attention is on the story, not on the telling.

Further, older people simply have far more to remember because they’ve got much fuller lives than young people do. Our culture’s obsession with youth not withstanding, older people have far more friends and acquaintances than young people do. They also have vastly more people’s lives and concerns to keep track of.

And since one very remarkable experience—that is, one good story—will touch on many aspects of life, in conversation with one’s older friends their especially good stories will come up from time to time, and they will probably not remember that they already told you that story three years ago. As I said, the story is far more memorable than the telling of it.

There are, at this point, three options:

1. Interrupt them to tell them they already told you the story.
2. Let them tell it then tell them that they already told you the story.
3. Let them tell the story and appreciate it again.

Of the three, the second is the worst option. It’s basically throwing a gift back in the giver’s face. Don’t do this.

The first can be polite, but it’s tricky to pull off. If the story is recognizable in its first few words, you can probably find a pause in the first sentence (or so) to interrupt and ask if it’s the story you’re thinking of—and bear in mind you might be wrong because sometimes different stories sound similar. If it is, then tell the friend how much you like the story. The danger of interrupting them is that you might seem ungrateful or unappreciative of the wisdom being conveyed and telling them how much you appreciate the story—not merely appreciated it in the past, but kept its lessons with you—will ensure that the proper reaction of gratitude is conveyed.

The third option is often the best option. First, because it is the most grateful option. Second, because the same story is often told with different details filled in, so one gets a more complete version of it by putting the two together. Third, because one will probably learn new things from hearing it again. And fourth, because the impossibility of perpetual novelty (while maintaining quality), happiness depends upon the ability to appreciate good things one has already experienced. Hearing a good story again is excellent practice at this.

One should not lie and pretend that one has not heard the story before, but it almost never comes up, and if it doesn’t, there’s no need to bring it up.

And you’re vastly better off having heard the same story twice than not at all.