[pg]

I was about to capitalize the S because I thought this was going to be about how to write a Smalltalk implementation.

As for your actual question, sometimes the conversation dies because the other person wants it to, and you'd seem pushy if you tried to force it to continue. But in borderline cases I recommend asking the other person about their feelings about relevant things.

I was a peer conselor in college. They taught us something called Rogerian Therapy, which consists of adding as little as possible of your own spin to the conversation, just asking questions, particularly about how the other person feels. You can't be too obvious, or it gets annoying. But if you're subtle about it, people just open up.

[spydez]

As an introvert, I really, really (really) hate being on the receiving end of this endless follow-on questions type of 'conversation' (can it be a conversation if your only participation is to crowbar more words out of me? (I digress...)).

"The only thing a true introvert dislikes more than talking about himself is repeating himself," as an article in The Atlantic once said. So be careful about using this Rogerian Therapy on shy people, and please don't use it on me.

[radu_floricica]

If you're picking... please don't confuse shy with introverted. Some people may be both, but it's definitely not the rule. It took me a while to realize I'm a bold introverted... I'm not afraid of interactions, I just prefer books to parties. Once the confusion was cleared I felt much better in my skin.

[pg]

I misdescribed it. When you do it well, you rarely say things that are grammatically questions. And you don't ask things you want to know: you ask about whatever seems most important to the other person. You could describe it as maximally unselfish conversation.

[paulgb]

My trick for when I'm in one of these conversations: after answering, ask "and what about you?". That is of course assuming the question is applicable to them (eg. "do you play any sports", but not "where did you get that shirt").

That way, you show that you are interested in the conversation and the other person. And often with these open-ended questions, people ask them because they have a good answer. (I know it seems narcissistic, but asking yourself "what question would I like asked of me" can be a good way to come up with questions.)

[stcredzero]

As an introvert, I really, really (really) hate being on the receiving end of this endless follow-on questions type of 'conversation'

You just helped me have an epiphany about my girlfriend.

[qaexl]

I default to being introverted too, and having follow on questions like that typically annoy me. (Probably one of the more annoying one is, "Are you OK?" asked by well-meaning friends).

Having said that, I have happily chatted with random strangers before, both receiving questions and initiating them. The difference is usually in how much the person who is asking the question is genuinely listening. Asking questions for the sake of making noise irritates me. Asking questions because you are really are curious works a lot better. When you are curious, you don't come from the position of "I know everything" or, "You should talk to me because I am awesome" or "You shouldn't talk to me because I am a loser."

As for awkward silences themselves, I think it is better to practice being comfortable with them so that the silence feels natural instead of being awkward. You're rarely going to be somewhere completely silent and most people generally have a running commentary running in the back of their heads. Awkward silences feel awkward due to self-doubt and anxiety. When you shed the anxiety, interacting with people feels more natural; distracting or forcing yourself with smalltalk doesn't really get rid of the anxiety. Being genuinely curious ... like exploratory programming ... tends to shed off the anxiety.

[pookleblinky]

I just got a horrible mental image of someone using M-x doctor to practice smalltalk.