Decide what you will share about yourself. Sometimes, women feel nervous when having a conversation with a man, and being unsure what else to discuss, proceed to talk about previous relationships, health problems and other personal topics that a man would feel uncomfortable hearing about on a casual basis.
Learn about his interests. If you will be having a conversation with a man who is friends with one of your friends, find out what his passions are. Then determine which ones you could discuss intelligently. You may both enjoy the same genre of music, or be avid hikers. Having a topic or two in mind beforehand can make conversation seem really easy. Remember that most people like to talk about themselves. Tying the conversation into his interests can get the conversation rolling.
Ask open-ended questions, as opposed to questions that can be answered with a simple "yes" or "no." If you ask a question such as, "Did you get your degree at Michigan State, like your friend Bill?" then he may tell you the dreaded one word answer. If you ask, "Why did you buy a Ford instead of a Chevy?" then prepare to hear an avalanche of words.
Asking questions will keep the conversation alive. If he tells you that he worked late, ask if he has to work late often. Work your questions into the conversation casually, lest you sound like a reporter.
Relate his responses back to your own life. This technique can be an effective way to both keep a conversation going and make a connection if you do it judiciously. Be careful not to do this every time he makes a statement, or it will sound as though the conversation is all about you. When he says that his brother went back to school to get his degree in art, it might provide an opening for you to mention that you once took some art classes before you decided on your major.
Make eye contact. Continually glancing away can make a man feel unsettled, and perhaps even a little insecure. Making eye contact will make him confident that you are interested in him, and what he has to say. It also makes you look more confident, even if you don't feel that way inside. Be aware of your body language as well. Sitting with your arms across your body will make you appear closed off and difficult to talk to, while having open body language makes you much more approachable. Learn more about attentive body language in the resource section.