In an earlier conversation with my friend and roommate Tom, I learned part of his personally-tested theories on the art of conversation with strangers.
The key to conversation is to talk about things that people are really interested in. But for strangers, you do not yet know what they're interested in so you have to make educated guesses as well as focus on topics that most people care about in general. And in any typical conversation, there are four basic topics that people are really interested in: sex, music, politics, and religion. Many people avoid these topics because they can cause controversy, but in fact they are the best things to talk about because they tap into things that people deeply care about, meaning that the conversation that ensues can be meaningful and hence create a real bond.
Though starting a conversation is more an art than a method, there are certain basic strategies. Observe what the person is wearing, because people wear things, most of the time intentionally, that display their basic values and interests. Then, on your approach make a comment indirectly related to that topic which you think that person is likely to have a strong opinion about. In this way, you can open up the possiblity of talking about something meaningful to that person, which will engage that person with you and make for a good conversation. After a conversation is started it will go where it will, but starting it by segueing into a major topic right off the bat will open the possibility of a substantive interaction, and hence a possible social bond between you and the stranger you have approached.
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