"The waiter had a strange feeling on his face after the tip." This would indicate that the waiter physically feels something on his face. The word you're looking for instead of "feeling" is either "look" or "expression." Even then, the sentence still sounds clunky. Also, as charitable as Bill Gates is I doubt he'd leave such a small gratuity, but I get the moral of the story. I'm just someone with too much time to nitpick.
Secondly, what does Rachel Leigh Cook's picture gotta do with the story...