"I've been friends with someone for at least twenty-five years now, and I love her to bits. She's a doll. We used to sit and have coffee every morning (she lived right down the street), but then a couple years ago she moved to a different state. I see her about twice a year now, but every time we get together she brings up things about my past, like mistakes I made or things I did when I was younger.
"I'm starting to dread the times we get together now. I've tried to make a joke about the things she says, like "Oh, well, we all did dumb things when we were younger" but she just doesn't seem to get it. What should I say to her?"
It's interesting that this change in her bringing up the past happened only after she moved away. Perhaps she is reminiscing about your friendship more since she moved, but what is an uncomfortable memory for you (bringing up the mistakes of the past) is a fun memory for her. She might even look back to those times as the best in your friendship.
However, if it bothers you, you have to do more than just drop a hint. Hints are only good if your friend can pick up on them. If not, you have to be more direct, especially since you're no longer looking forward to the times you spend together.
On the next visit, see if she brings up yet another story from the past. Then, ask her why she has chosen to talk about it. You could say:
"Funny that you bring that up, it was such a long time ago that I don't even think about it anymore. What made you remember it?"
This question is good for getting to the bottom of why your friend is suddenly bringing this up. This can help you talk to her about why it bothers you. For example, if she says, "Oh, I've been thinking about all those good times since I don't have a best friend since I moved" you'll be able to sympathize with this new stage in her life. You'll also be able to see that she's bringing up the past because she's struggling with making friends in a new city.
However, you need to add that these memories are not comfortable for you. Regardless of the reason she gives for bringing up these stories, tell her something like:
"You know what? When you bring this stuff up it feels a little like you're making fun of all my mistakes from the past. I know that's not what you're trying to do, but I have to admit our recent memories are much more precious to me. Why don't we focus on that instead?"
The point to remember is not to get angry until you understand where she's coming from. She may not even realize she's doing this. Since she's a good friend, she won't want to hurt you, so politely telling her that these stories bother you will make her take notice. You two didn't get to be friends for twenty-five years by being neglectful of your feelings. Trust the positives that have helped build your friendship as you navigate this new season of your friendship.
If you speak to your friend and she continues to bring these things up, you can be a little bit more direct, saying something like:
"I enjoy your visits, but bringing up these memories from the past makes me feel like our friendship is moving backward. I told you it bothered me, so let's put these aside, okay? Twenty-five years is too long to let a friendship go, and I fear that if we keep talking about the past I won't want to get together again. We've got a lot of positive memories we can talk about instead."
If all else fails, you can get together less and less until your friend gets the point.