Makeup advice for a fourteen year old girl?

OKay, so I really like this boy. And he looks like alarmingly good. Well, for a punk rocker kid. Yeah he's a punk rocker.Blue peircing eyes, and sharp thin features. And hes like bone thin and very tall.
Anyway, I don't know. I want him to notice me. I want to look attractive. Lets, just say, im not the prettiest girl.My nose ruins everything, but at certain angles I look cute.I wanna start wearing makeup. Permanently. This is a huge step for me, because I pretty much am the biggest tomboy of my age range. Like I will go to school looking a mess and I wont care.Mainly because of my punk style. But I wanna start wearing dark dramatic eyeliner on my medium dark skin. I don't want to wear a lot of makeup, because I don't wanna become dependent on makeup to look pretty like all the other clone girls.Im smart, and all of my friends are guys.My best friend is a guy.But because I hang out with guys the machoness becomes a part of me and sorta subtracts from my gentlre female like nature.
So is it okay if I wear it 4 days out of the week? ANd maybe even switch it up?How much makeup is tooo much makeup on a dail basis.