Usually if I'm the one taking a picture (so, selfies) I am fairly pleased with how I look in it. When someone else takes the picture, I am invariably not happy with how I look in it. Although, I guess when it comes to selfies, I can take a lot of them and have control over which ones I actually show other people, which probably has a lot to do with it.

That's a good point about personality - photographs are very flat and just a specific instant in time; it's very hard to capture the essence of what makes you you in a still shot like that. :)