Keeping people interested in a conversation is based on who you are and on what you have to say. If you are having a conversation with a friend, your conversation can be on anything and your listener can either listen or just let you talk. If you are sharing confidences, he will listen and the interest level is there because you are talking about people or events that you both share in your personal space. Here's how to make a conversation interesting.
But if you are dealing with an enemy, whether known or secret, keeping his interest becomes more difficult. Your listener will not be listening to you as he has pre-set barriers already formed against you. He will not let you reach him because you have been put on his enemy's list. Trying to engage a known or a secret enemy in a conversation that is interesting can be done if you persist in engaging the other person, you don't raise your voice and you don't bring up any topic that has caused that person to view you as a foe. The old trick of eye contact always works.
Regardless of the situation or the people you are attempting to have a conversation with, the old laws of eye contact, being polite and allowing for the other person to respond, showing empathetic concern, and joining with one or two people in the group as partners, will keep your conversation lively and the people interested.
Don't forget people are only really interested in conversations with other people who know about them, have something they want, and who share common interests. If you were listening in or joining in a conversation with someone who was an elected official, your interest would be automatically aroused because you want to know what people who are in charge of your future are thinking. How to keep people interested in a conversation means learning to keep them alert by asking them questions and waiting for them to reply.
No matter how interesting you may be, if you are not involved in a shared conversation, your listening friends may dose off or go about doing their own thinking. Keep in mind that a conversation is not a lecture. During a lecture, people listening are alert and taking notes because they know that they will have to respond in a test or written paper about what you were discussing. During a conversation, people know that you are just talking and they are not obligated to be interested in what you are saying.
If you listen to people who are great conversationalists, you will find that you are interested because what they say is about events and people and not self-centered recounting of their impressive day's activities. No matter how interesting you think you are, people listening to you think that they are even more interesting. A chatty conversation that takes people away from their concerns and joins them to you in shared human bonding also known as conversation will keep them interested.