http://img3.imageshack.us/img3/1065/110131185516.png
http://img138.imageshack.us/img138/4378/110201155714.png

I look sick in those pictures; I think I was..

Anyway, I'm thinking of changing my style to a short bob this summer. However I presume that will make me lose my ability to pass as a boy. Everyone says I look like a boy nowadays; that there's nothing remotely girly about me. 

One like this: http://hairstylesup.com/wp-content/uploads/2009/05/short-bob-hairstyles.jpg

But with red highlights.

I don't care if I look like a girl, as long as I look like a boy that looks like a girl (or androgynous).

I think your face passes as male so I think you'd be fine with the hair.

I have hair kind of like that only longer, and I find it helps to hide the roundness and feminine shape of my face a little bit so you'll probably be quite content with it.