2. Get one of those free makeovers at the makeup counter
I took off yesterday afternoon to get new glasses. And when you're waiting for "about an hour" until your new glasses are done, do you know what else you have time for? A makeup lesson! The Clinique counter had someone relatively unintimidating behind it so I went over and explained "These are the products I have, I would like to know how to use them better to get a decent evening look". I ended up with one new liner, one new shadow and a much better brush. And a solid hour of discussion and experimenting.
Thus far it has been determined: my current base coat is good and I will keep using it (it is the more gray one). I also might look for a taupe-y version of said base coat. My current shadow/liner combo is low-sparkle shades of green and is a nice low-key look over previously mentioned base coat. My new shadow/liner combo is a smoky gray-violet and is a nicer evening out kind of look (also works with aforementioned base coat). I also learned about putting the little wing on the outside of my eye with liner and doing the accent color in the crease instead of just covering my whole lid with shadow (although the whole lid still gets covered with base coat). I don't know if any of that made sense but I'd read about this stuff in magazines and it makes much more sense when somebody is demonstrating it on your very own face.
And I officially don't like highlighter, be it on my brow bones or in the inner corner of my eye (to make my eyes "pop"). I don't think it brightens so much as makes me look greasy. And this was true of more than one product so I am pretty committed on this one.
P.S. I am such a Clinique fan I have to plug them - if you buy from their website they send you all sorts of deals for free samples and I have found out some great products that way. Also, free shipping! And I have annoyingly sensitive skin and their makeup is relatively non-irritating and doesn't seem to make me break out. Neutrogena is my other current go-to but sometimes it is just easier to have somebody walk you through the process and you don't get that so much at the drugstore. She didn't walk me through a whole-face application but I'm sure she would have if I had had more time. Still, it was really helpful and I am very glad I went.
P.P.S. Do you know how hard it is to find a decent pair of black-framed glasses? There is apparently a very fine line between "sexy librarian" and "dirty hipster who wears his girlfriend's jeans".