How do I converse with someone

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I don't know how to keep a conversation going with a person and having one always feels awkward. I get lost with having to say something that will keep the conversation alive, or make it feel meaningful. If this happens the way I speak tends to have a depressed sound to it. How do I get a lively conversationg going, one that doesn't feel awkward. Conversation just generally doesn't feel natural to me unless it is deep and involved in something that can interest me. How do I break into something meaningful, or make my conversations feel more meaningful?

In a general way, be interested in the other person. There won't be much conversation if you're with another person but you're only thinking about yourself and your awkward situation. So stop thinking about yourself for a minute, and be interested in the other person.
Two specific ways I've been told, by normal people I know are:
Ask someone how their work is going. Most of us like to talk about our work situations.
Ask someone two questions about themselves.
.....do you have children?
......do you have to take them to early hockey practices?
.....are you a sports fan? well, what kind? how far do you run? do you do any races?

Ron