Hmm, I have a few pairs of heels in different styles, and I'm always in pain. I have inserts in all my shoes, they are a must. My right foot is more problematic for me, there's a certain pressure around the ankle that makes it more painful. When I get some health insurance, I'll definitely have to try to see a podiatrist (sp?). I always wonder if it's the shape of my feet or some other issue.