What does being cool mean? The definition may be different for everyone, but in general being cool means that you are a positive person that others want to emulate and be around. Often being cool is associated with being popular, but true coolness comes from within and not from outside influences. If you are cool then you are not moved by negative events as much and you tend to have a happy go lucky attitude. Cool people take lemons and make lemonade, and they do not let life drag them down.