Really nice write-up! I want to add that if you are already in a relationship (long term) and you both enjoy however you do your makeup already, then don't feel pressured to change whatever you're doing, whether that'd mean more or less makeup.

Of course, asking for his opinion of what you do is never bad either. I don't mean asking, "Do I look bad with this much eyeliner?" but asking things more like, "Do you like it more when I do my eyeliner like this or like this instead?"

Learning a five minute "minimal face" is also good for any occasion. I go without makeup as often as I go with full makeup, and have recently learned that finding an inbetween for when I'm in a hurry makes me look more put together overall.

Also, you can improve your natural beauty with proper skincare, moisturization, etc. A bare, soft face that is blemish-free or relatively blemish-free will always look better than a bare face with lots of acne and/or dry skin. And it goes without saying that when your skin is healthier it makes applying makeup easier!

First comment here, by the way :) I love makeup and beauty-related things, so I was a little compelled to share my thoughts.