Alright. So after much frustration caused by bad conversationalists, I've decided to write a little guide on how to have a decent conversation. This guide will focus on a text conversation -- I feel that actual vocal conversations seem natural enough where it's not too hard to keep it going. Additionally, assume that this conversation is between relatively good acquaintances. You shouldn't expect good conversation from people you've just met (but they should still be able to provide it).
Person 1: Initiation. ['Hello', 'Good morning', etc.].
Person 2: Return greeting. Now, person 2 has another option. Since he/she did not initiate the conversation, he/she is not obliged to say anything further at this time, but the return greeting could be supplemented with and inquiry (explained in the next step).
Person 1: If person 2 did NOT follow their greeting with an inquiry, this is the time for that. This is easy, just ask a simple question ['What's up?', 'How are you?']. If you want to make it slightly more personal, ask something deeper. This can change for morning [Any big plans for today?], afternoon [How's your day going?], and evening [How was your day?].
Person 2: Answer the question they ask. Keep it brief, but don't be vague. No one wants to just hear "Not much" or "Just chillin'". If they ask about your day, don't just say "It was good". Give a little detail. Mention the highlights (or lowlights). A couple sentences should be enough. End your message with an inquiry directed at them, similar to the one they directed at you. NOTE: this final part can be skipped if you mentioned a major event or something that you know will spark an obvious question (eg. "I got into a car accident" or "I found the most amazing thing ever".
Person 1: A) If they add an inquiry, answer it as described above. If not, skip this and go right to
B) Comment on their response. Ask another question relating to their answer, if warranted [You got in a car accident?? Are you okay, what happened?]
From this point on, each person should continue asking questions and providing a brief (2-3 sentences) but relatively detailed responses to the questions they're asked in return. This should continue until the stories seem to run dry. At this point, one of you should use another initial "inquiry question". If you began with "How was your day?" you could ask "So what are you up to now?" when the first part gets dry (and vice versa).
This process can be as short as 10 minutes, or as long as a few hours. The key is to make sure your response warrants either another question or comment -- this is how conversations flourish. It's all about momentum, and doing your part to keep things going.
CONVERSATION TIPS IN A NUTSHELL:
1) Ask plenty of questions, and provide thoughtful answers.
2) ALWAYS AVOID single-word responses. "Haha", "Cool", "Yep", "Good" etc. might answer a question, but does nothing to keep the conversation alive. Keep them away.
3) Think of a text conversation as a transcription of an actual face-to-face conversation. Imagine you're actually SPEAKING to the person, and type out what you'd actually SAY in response.
ADDITIONAL TIPS:
1) Make sure you seem genuinely interested in what the other person is saying. You may be interested, but if you don't show it, the other person will assume you're bored.
2) Don't be afraid to use exclamation points and emoticons. Body language/facial communication is completely lost through text, so adding things like ! :( :) :P to show excitement, humor, anger, concern, etc. can help mimic what's being lost.
3) If you know you're about to fall asleep, say goodnight. Don't just ditch on the conversation. Same goes for if you know you won't be able to respond for several hours. Let the other person know you're not just ignoring them.
4) Don't just forget you're talking to someone. It's incredibly rude.
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