Isn't it funny how 8 times out of 10 when people tell you what you said was interesting they mean precisely the opposite? We've all done it. We've all heard it. It is usually the surest sign that the anecdote you just told totally blew. Maybe you told it wrong, or maybe they just don't have a clue what you are talking about or why it matters---whatever the case, it was anything but interesting to that person. Yet it is the most polite of conversation closers to say: "Wow. Interesting. Hey, is there any potato salad left over there?"
Best case scenario: They just weren't following. You were assuming you were on the same page from the get-go and were mistaken. Given time and another chance you could show how interesting and sensical your anecdote was, and find and enjoy some common ground.
Worst case scenario: That person finds you an incredible bore and you must come to grips with the startling truth of that possibility without concluding that they must be from another planet.
I think it is a great gift to be able to be interested in anyone and anything. My Grandma is really good at this. She listens and tries to see what is so interesting to the speaker that they would choose to speak these words in conversation rather than the millions of others they could have chosen. I've tried to get good at this too. After all, it comes back to believing the person your are talking about is a person made in the image of God. There must be something remotely intersting there. Curiously, even though I hate fishing, I almost came to enjoy it through the passion of the avid fishermen I met and listened to and grew to appreciated in Manitoba. (I'm pretty sure Rob doesn't read this, but hello Rob!)
Trouble is, I generally start with the assumption that very few people find the same things interesting as I do, so I pass off questions about what I'm into and then get to my task of listening to others. This has been good for me and I've learned a lot about the world and learned to love people, but it can get pretty lonely too. You sure do need people around you who are interested.
And here is the thing: You also need people who are interested, not just becasue they happen to like what you like, but because they are interested in you. It is great to have a groups of friends with common interests, but we also need a groups of people with a common love. Not a love of some hobby or project, but a common thing inside them that makes them appreciate the world, and others, and expecte to see something of God, something lovable, something true, in everything.
This is part of the reason I don't like churches choosing target groups, subconsciously or consciously, as most do. It makes church easier and more enjoyable, but it somehow diminishes for me the reason we get together. At worst it creates a "false unity", in that we are saying we gather because of Christ but we really gather for something else.
This is also part of the reason I try to steer the conversation elsewhere in the church foyer whenever someone seems to be making small talk for small talks sake, talking about something even they aren't interested in! Those conversations are the worst! I'd rather stand in silence.
But honestly, if the person talking is genuinely interested, it should be at least theoretically possible, given time, to find out why. Its just a matter of how far apart you start and how much time and love you have to give.
Chesterton wrote a very true thing: "There is no such thing on earth as an uninteresting subject; the only thing that can exist is an uninterested person."