Humor is good, so is asking question that do not require a one word answer. For Example: How was your day? it can be good/bad. But if you ask What exciting things happened to you today? They have to elaborate and mostly will feel that someone cares. In your humor it has to be not confrontational or aggressive. Your wit will sharpen with practice. Roles models are important; I think you should choose at least one from two categories. The first should be a real life person, imitate as much as you can without being too obvious. The second should be a sophisticated celebrity. Also watch news and sports, talking sports is a sure bet to extend conversations. Tune into C-Span sometimes, you will notice patterns to the rhetoric if you follow it mindfully. Lastly you must be discerning in words, does time allow for a conversation or just a quick hello, learn these peoples names and use their names often.