From my personal experiences, there are two main ways to keep a conversation flowing. First method is to ask questions. For instance, person A asks "How was your day?" Person B replies "Oh.. pretty good, just the usual." Now, at this point, person B hasn't done HIS part and asked the question "What about yours?" Sure, one can argue that person B isn't in a talkative mood and wants to be left alone and this is why he didn't ask anything in return. One can also assume that person A might be an awkward creeper and person B wants nothing to do with him. All of these issue aside, when someone is making the effort to get you to talk and he is interested in the conversation, you should return the favor and ask him questions in return so he has something to work off of as well. Once again, this is assuming the person you are talking to isn't someone you actively avoid. This is perhaps a big assumption.The second method to keep a conversation moving is to comment on something the other person has said. For example, person A says "I am really pissed off at my colleagues, they are always trying to use me to get ahead." Person B replies "I've had similar experiences with my coworkers, they don't seem to care about friendship, just career advancement." At this point, person A can comment on what person B has said or person B can finish his statement with a question and person A can continue from there.
Given these two methods, I observed my own conversations. I noticed that I seem to ask a lot of questions when the person I am speaking to is NOT asking me anything and is also not responding specifically to something I have said. As a result, I am forced to keep asking questions to keep him/her talking and it becomes an unpleasant experience because I get the feeling I am interrogating the person instead of having a healthy conversation.
So please, if someone is asking about you, RETURN THE FAVOR! However, you have to first make sure that the person you are speaking to is actually giving you a chance to ask questions instead of cutting you off with more and more questions without giving you the opportunity to ask anything.
(image link: http://www.mightyinkcomics.com/wp-content/uploads/2010/08/mario.jpg)
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Hark Triton, hark! Bellow, bid our father the Sea King rise from the depths full foul in his fury! Black waves teeming with salt foam to smother this young mouth with pungent slime, to choke ye, engorging your organs til' ye turn blue and bloated with bilge and brine and can scream no more - only when he, crowned in cockle shells with slitherin' tentacle tail and steaming beard take up his fell be-finned arm, his coral-tine trident screeches banshee-like in the tempest and plunges right through yer gullet, bursting ye - a bulging bladder no more, but a blasted bloody film now and nothing for the harpies and the souls of dead sailors to peck and claw and feed upon only to be lapped up and swallowed by the infinite waters of the Dread Emperor himself - forgotten to any man, to any time, forgotten to any god or devil, forgotten even to the sea, for any stuff for part of Winslow, even any scantling of your soul is Winslow no more, but is now itself the sea!