No, really. What did you expect?

For him to roll for "Diplomacy".

Isn't that exactly what he did?

Since he's punching it in the pupil, wouldn't his fist just... go through the hole? I mean, I guess he could end up punching the back of the inside of the whale's eye, but...

There is a lense over the pupil itself, there has to be to keep dust from just getting into your head.

Well, if nothing else, he's staying in character.

Called Shot to the Eyeball!

Having the navigator stunned in this situation might not be the best situation.