This is first time actually contacting you, or anybody through blog for that matter. But you make it almost too easy(you must be bombarded with e-mail, good luck!).
I'm interested to know your strategy or preference on maximizing meaningful conversations abroad or even back home. I mean do you have any particular tactic or is it mostly random. Any public places or events that stir up conversations with strangers, any small talk lines or questions(etc. Where do you see yourself in 5 years?) that lead to insight and good conversation.
I'm from Finland and I'm going to travel a bit in asia(Okinawa, Seoul, Katmandu, Bhutan) and I find conversations as the best way to learn and experience different cultures. It would be such a waste to do it randomly if it there's is a way to do it most efficient way.
If you have any book recommendations, please make them available in amazon.co.uk with your affiliate id I would be happy to support you somehow.
Thanks for dropping a line. Yes, I don't like smalltalk, and I do like interesting conversations. Some thoughts that might help -
1. Have interesting questions: A little learning, research, and preparation about the culture you're visiting goes a long way. I can't tell you what specifically you should look up, because it would depend on your taste. I like history, so I study the history of anywhere I visit. If you were interested in contemporary politics, you could brush up on that. If food, then learn some about the food before you go. Then you can ask, "Hey, I've been learning more about [topic], but I was wondering..." and then ask a question - that'll make for interesting discussion.
2. Learn 10-20 words of the language: Well, learn the whole language if you can, but even 10-20 words goes surprisingly far. Hello, thank you, hungry, happy, friend, like, dislike, a few adjectives, a few verbs... these go a long way. In some cultures, you almost have to learn a certain phrase or two to get by. For instance, I find French people very friendly and cool if you say, "Pardon. Parlez-vous anglais?" (Pardon me, do you speak English?) Really, just a few phrases goes surprisingly far.
3. Go places interesting people go: Again, this depends on who like you to mix in with, but some places are conducive to socializing and friendly and meeting people, and some aren't. The cafes and bars in hotels tend to be pretty sociable, the ones that cater to locals mean you'll meet people from the country but who are on business or tourism in the capital or vacation city.
4. Practice gently wading into touchy topics: If you want to talk about controversial things, there's a certain elegance that's more or less required to do it. I'd brush up on how much free speech is available where you're going - as a visitor, you're fine, but locals will be more careful about criticizing the government in public in some places. (This might sound surprising to you, but in probably a majority of countries people will be afraid of at least a little repercussion from speaking ill of the people who run that society) So, learn how to wade in... "Y'know, about XYZ war that happened, sometimes I think the conventional view of it might be a little off..." Then you kind of size up how comfortable the person you're talking to is. This is especially important for talking war, politics, government, corruption, mafia, things like that. Make kind of a fleeting remark at first, and let who you're speaking to see if they're cool with the topic.
5. Defend their culture's controversial points if you want to talk about them: A lot of people are politically correct and cautious. If you're get a feeling like the person has some controversial viewpoints but they're giving you a politically correct line of thought, try to declaring strongly in favor of their culture. For instance, when history comes up with English people, you'll usually get a politically correct, "Well, the British Empire did some good things and some bad things..." I typically reply, "You think so? I think the British Empire did the most good in history, overwhelming good, the most civilized and prosperous and good nation in history. The bad things pale in comparison, and almost everywhere the Empire conquered were worst before and better after." If you speak out in favor of a person's culture, you can often get past the politically correct versions.
Beyond that, I find it typically easier to get past smalltalk when you're meeting just one other person - people are a lot more cautious in groups. Do feel people out a little bit - for instance, I found in Seoul that almost nobody wanted to talk about North Korea or Kim Jong-il, both sources of major embarrassment to most Koreans. But it's surprising how not-touchy other subjects are... you kind of figure it out when you feel people out.
Far and away the biggest thing is to have some knowledge about aspects of the culture that interest you, so you've got intelligent things to ask. Also, getting past smalltalk on any topic makes it easier to get past on every topic, and thus talk about money or sex or war or politics or religion or whatever. So, start by brushing up on an area or two about the country that's fascinating to you, which should help have more interesting conversations across all domains.
Re: books, I should put together a general recommended-reading list sooner or later, but I got nothin' on that score right now. Still, thanks for that offer, and safe travels and godspeed.