Compliments are hard to take for some, and it sounds like you find it patronizing and creepy. This is for this very reason that I was really hesitant as a woman to compliment men, I'm more or less the same generation.

One time late at night, I had no makeup on and was very frumpy, going to buy a six pack at 7eleven. There, a gorgeous gigantic drag queen told me "Giiiiiiirl, look at your faaaace, you're so gorgeous". It was so so so cool and made me feel like a queen. So from then on I thought fuck it, I don't get compliments often and when I do, it makes my day. So now I do whenever I am sincerely impressed or enjoy something.