Conversation should incorporate multiple thread theory. You should have several stories running at once. For example, you start a story about going on a trip with your friend Barney. You and he visited New York City. So somewhere before the end of your NYC trip story, you can break off and go into a story about Barney. Let?s say he is a horse trainer. So you start a story about him and his horses, then break off and go to a story about you getting thrown from a horse as a kid. Now before the end of that, maybe pick up your NYC story again, then jump back to your Barney story, then your horse accident story. Multiple threads running at once give the feeling to the target that you?re covering a lot more ground, compared to going to the end of one thread and then picking up a new one. This is how old friends talk to each other, and it conveys this kind of familiarity.