I personally would never date a girl that wears a lot of makeup, a little eyeliner or whatever that's cool. If you need makeup to make you "look good" then you have some real issues to address. My ex, who i'm still really close with doesn't even put anything on but a little mascara anymore because I made her realize how beautiful she truly was. Shit we met up for dinner a couple times and she came in just sweats and a tshirt because of how comfortable she is. Someone doesn't see you for how beautiful you are without makeup on doesnt deserve you at all! She did end up choosing girl's over me but that's just nature not my fault lol
I find this so incredibily offensive. Some of us do not wear makeup just to "look good" for YOU or any other man. I enjoy the whole ritual of makeup. I am a very pretty woman without the makeup. I do not have low self esteem, I do not NEED it to make me look good. I ENJOY it. So not all women who wear makeup all the time have issues they need to address. Maybe you need to address why it is that you need to push a woman to not wear makeup to please your own idea of beauty.