I suppose, most people of your passion being writer and musician are introverts. How about a little research of his point of interest aside from your the discipline you are both in? Then start being energetic yet tactful in approaching him. Smile and greet everyone including him so it won't be obvious that you are singling on him. Try to find way of impressing him.

About self confidence; strengthen your belief on yourself, discover your extra ordinary capabilities and always feel good about yourself. Feel proud of yourself.