I have been sitting here for about ten minutes trying to think of the right word for a certain something. The best way I can describe the feeling is if someone was watching a video in which someone did something horribly stupid, and injured themselves in the process. A third person would say: He/she looked upon the stupid man with >emotion that expresses: "Why the heck did he do that?"<
Confusion, distain, pity? It all kind of depends on what you are trying to convey about the character.
You've described the feeling sought by aficionados of America's Funniest Videos, or Jackass, or similar "entertainment." It's a mixture of smug superiority, feigned empathy, and sadistic pleasure.