Of course, there is always more to learn. :)
I highly recommend Dale Carnegie's classic How To Win Friends and Influence People. The title turns people off, but it is a classic "people person" book.
Just don't do it with a sneer on your face or contempt in your voice.
Either way, you should be able to enjoy talking about the human condition, friends, and experiences you've had. These are quite universal.
The cool thing is when you get somebody to really open up about their interests like this, you sometimes discover it really is interesting, after all.
The key is to offend people early so as not to waste time getting to know someone you'll hate.
Or possibly they just don't like rabid partisans who are incapable of discussing any subject outside their personal political beliefs.
"not to waste time getting to know someone you'll hate"
Yep. Automatically hating anyone with a different point of view before even getting to know them is definitely the way to go. It's called "diversity", right?
(Addressing all parents of this comment) Don't tell people to google it, just paste it in first and avoid all the distracting chatter so we can go read other threads.
Advice dog aside, that part is actually correct. Just dive right in. Say it. Start the conversation you want to have.
Don't worry about what they may think, or preamble, or leading up to it, or any of that.
If you've got something interesting to say, most people will appreciate that you just took the bull by the horns and started talking about it.
And even if not, most people appreciate someone who can steer away from awkward silences and boring small talk, no matter which direction they actually go with it.
That said, some of the True believers (politics, religion, programming languages, etc) are the nicest people. As long as you can handle non-rationality.
(Also, being Swedish originally, I'd rather die than offend someone in person; the internet is different.)
Edit: How about an ASCII face for "advice dog" comments? What I commented on could have been said by lots of cool people I know (they might not know me, though :-) ).
Same principle here.
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In regards to this, speaking to the underlying subject (sports, as per the article's kayaking example) and expanding from there can open more doors than simply mentioning a particular sport which few people do. So, expand kayaking to sports or what is so great about kayaking (ie, "it's great to get out of the office."), therefore the other person can have more things to talk with you about than just kayaking.
This goes back to something, of all things, I overheard on Dr. Phil when the show came on the air. The topic was about getting to the heart of a problem and the "hack" he spoke of went like this,
So, you're middle-aged and thinking of getting a red sports car. Ask yourself why you really want it. The answer might be, "because I want to feel young." Well then, what you want is not the sports car but the underlying feeling it can give you. Now, start over and ask yourself why you want to feel young.
Rinse, repeat until you find out what you really are after and I'll bet there are many more avenues to your destination than just getting a sports car.
I see you have awesome stuff in your pants.
So... do you wanna keep talking or what?
The very best conversation is going to be when you both happen to be interested in the same topic, in which case there's not much effort or social skill involved. That's easy.
The difficult part is when you're at a situation like the OP mentioned with a lot of "small talk" going on and you are struggling to talk with people, feeling awkward, etc. Perhaps you want to have a friendly conversation with your grandma who is not into computers. Perhaps you're trying to network at a corporate event or you're just trying to chat up a girl/guy, etc. People who are very social are masters of making other people feel that they are interesting. They are usually very skilled at getting you talking.
I kind of wish I had known this before I went to YC's Work At a Startup event.
1. Keep asking questions until you hit a nerve and find something you have in common with the person. It also works the opposite way. You can find a point of disagreement and talk about that. Nothing heavy, something as simple as "What? You hate country music? I love it! Why don't you like it?" can turn into a full on friendly conversation just the same as "Oh you work with Save the Whales too? How did you like that last event they had?" can.
2. Get a life. If you're a one-dimensional person who's all about one single thing you can't relate to anyone even if they have that one thing in common. I can talk to someone about web development for a long time but eventually talking about the same thing is tiresome. The more life experiences you have the more you can talk about and the easier it is to find things in or not in common with someone else.
The rest on that list are just variations on that theme. If you get a life and ask a lot of questions even the most introverted person can easily turn small talk into large talk (made up term).
: There have been some misguided attempts to appropriate for other purposes, but these are largely ignored in the linked article. cf. http://cukes.info/