I'm definitely not a conversation expert, (in fact I'm happier not talking to anyone), but a few things have helped me at least survive conversations:
- You have to be interested in knowing more about another person. If you lack interest, it could mean you're assuming so much about the other person that you feel no need to talk to them. Try to give them a chance to surprise you.
- Some people are naturally good at staring at each other and talking up a storm. You may not be one of those people. This is perfectly OK. You are not weird and there's nothing wrong with you. You'll just have come up with some "cheats" that will work for you. I personally have better conversations when I can do some fun activity with another person (e.g. play a board game, hike, etc). Some people work from a small list of memorized questions to get things going.
- Shutting up and listening is golden. Most people want to talk about themselves. You just have to ask good questions and let them go. When people feel you've listened to them, it'll make their day. Really. This is especially true when people are venting.
- Don't ever...ever..ever give advice or correct the other person unless the other person gives you explicit permission. I took a dance class one time and a woman sought me out to dance simply because I didn't correct her mistakes like some of the other guys. This is also a big one when people are venting.
- Notice how many questions they ask of you. If they ask you nothing, they are probably not interested in you, though this is not always the case. If you sense a lack of interest, move on ASAP to avoid a boring, long-winded, one-sided conversation.
- It takes two to make an awkward silence. If it happens, that means neither you nor the other person is able to come up with something to say.