Dreaming of a headache could indicate feelings of pain around the ideas of intellectual pursuits, logic, and rational thought. These ideas may have been a disservice to you in the past and that pain is coming through in your dream. Alternatively, dreaming of a headache could indicate that someone in your waking life is bothering or annoying you in some way – as in “giving you a headache.” It could also indicate that some aspect of yourself or your personality is bothering you.