Yes I did get quite surprised couple of times, like you know it's the same girl but at the same time the change was so pronounced it felt weird. And since girls look much more plain without make-up I felt a bit disappointed... As a general rule it's a good idea to see your girl without make-up as soon as possible.
The first time I met my boyfriend, I only had on eyeliner. So I think he was more surprised when I wore makeup (granted it's only eye shadow) in front of him. He thinks I'm really good at doing it so he likes me either way. Which is good because I like playing with my makeup.