In order to become more comfortable with Air Traffic Control (ATC) interactions, it helps to understand the job of the controller. The single biggest problem between controllers and pilots is a mutual lack of understanding of each other's capabilities. Controllers are not magicians who can read your mind and predict your intentions. It is easy for pilots (especially students) to assume that a controller has more information than he really does. By the same token, controllers occasionally issue instructions that are difficult or impossible for a pilot to carry out. The better a pilot understands the controllers job, the better prepared he is to anticipate and prevent potential conflicts.
Most control towers are happy to give pilots a tour of their facilities, and this benefits both the pilot and the controllers. Be sure to take advantage of this opportunity, especially at airports you regularly fly from. They will explain their job to you, demonstrate the equipment they use, let you watch them work, and answer your questions. The experience can be very enlightening, and can help you to better understand what they are dealing with. The better you understand their work, the better you will be able to make their job easier, which, in turn, will allow them to make your job easier as well. An added benefit to doing this at airports you frequently use is that you will meet some of the controllers you deal with in person. Putting a face to a voice can often help make the communications process easier.
It can also be beneficial to try your hand at an air traffic control simulator. There are several such products available, and even though they are intended primarily for entertainment, they are realistic enough to help a pilot get an idea of the kinds of challenges faced by controllers in real life. Two products of note are ATC Simulator 2 and Tower Simulator.