No... i would not pretend to be sleeping and take a picture of her who is actually trying to sleep (with the eye mask on) ... when she has no idea whats going on.
I would, however, ask for a picture while she is awake.
I'm not sure what I would do...
If he was genuinly trying to tap that (you never know) may be he didn't want to ask for a picture with her (like that he could keep the image of a "cool guy that doesn't care about her celebrity status"), but
at the same time he wanted something as proof.
Plus this is a celebrity... Snapping pictures of a girl you don't know would be f*ing freaky, but this is a celeb. Think of all the paparazzi photographers spying on celebs from trees and shit lol
Anyways would be nice if that guy answered, like that we can get more details...