The best conversations come from gaining new understanding about the topic discussed or the person. Lead conversation into personal stories and vibrant debate such as politics, community issues and news around the country. These give limitless conversation and are revealing about the character of a person.
It's okay to talk about yourself as long as the person listening is interested and getting new information about you or the topic. People don't like to rehash things they already know or have thought about so try to give a new perspective or way of thinking.
While you want to talk about a topic, make sure you pause in between sentences, which allows for the other person to ask a question to clarify if they understand you and/or for them to interject with a thought of their own. Remember, you want to have a conversation, not be a story-teller.
A compliment usually does the trick. For example, a "I like your shoes" could lead to a conversation over stores, shoes or anything.
Always make eye contact and be sure the person knows you are listening. Some people like to half-listen and usually make horrible conversationalist. If the person is doing this or is doing it often or all the time then they're not the person you want to have a conversation.
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