How to check if a path fits inside of another path?

I've just been told that I need a script that will check and see if a path fits entirely within another path? In my case, I need to see if a GroupItem fits within a circle of a specific size. I don't see any methods available for PageItem that will do it for me, so does anyone know of a workaround? (Preferably without having to check every single PathPoint of every single item in the group.) I am using Illustrator CS6 and do my scripting with Javascript.