As you mentioned, I believe it's all contextual. The easiest and most natural way I feel is to always smile, greet the stranger and introduce yourself. At that very particular moment, you're no longer total strangers. At least one party knows something about the other. After that, if it's the context of an event, there has to be some commonalities or shared interest to at least get a conversation going. And as folks warm up and loosen up conversations will carry on to...
In any other context, just being a human who relates to other humans will help you strike up a conversation anywhere, anytime. Simply practicing that habit without after thought, can improve ones quality of life many fold I'm sure.
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I don’t know... introducing yourself to a total stranger can be super creepy in certain situations.
It is creepy but it totally depends on how you adjust yourself according to the situation. You may have some diverging interests but you should always keep the stranger in comfort zone by giving him/her the feeling that you are very interested in what they are saying.