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CronoDAS comments on How to always have interesting conversations - Less Wrong
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Starting a conversation with a completely random stranger generally takes skill to begin with. Potentially creeping out 20 people in a row is not an acceptable risk -- unless you'd like to bear it for me?
Also, others who have posted on the topic [1] said that if I'm at a low skill level at this, I shouldn't practice on people in captive situations, like being in line at the bank. Which of you should I believe?
[1] can't find the link right now, and I can't even mention one of the people's names
I think I've come up with a reasonable algorithm for determining if a stranger is open to conversation. (Mostly tested on females in New Jersey.) I developed it out of desperation, because, for a while now, if I didn't talk to strangers, I wouldn't be talking to anyone in person except my immediate family.
The algorithm:
Smile and make eye contact.
If eye contact is not returned within a reasonable period of time, find someone else. If eye contact is returned, wave.
If the stranger waves back or shows some other noticeable positive reaction, go ahead and introduce yourself.
The key seems to be the eye contact; as far as I can tell, if someone is willing to make eye contact with you, they're usually willing to talk with you, and making eye contact seems to be inoffensive in most situations. You'll probably get some false negatives, but false positives tend to be worse than false negatives and the false positive rate seems to be almost zero; you usually don't creep people out by deciding to leave them alone.
Also, fan conventions (anime, gaming, etc.) are great places to find people willing to socialize with strangers. And take a camera; people often wear elaborate costumes at these events, and complimenting someone's cosplay outfit has been a good conversation opener for me. (This is me at Otakon 2009.) I've also had some luck talking to fellow customers at bookstores; you know a few really good books you can recommend, right?