LOL I totally get you!! I haven't ventured into the whole lipliner thing myself, I like just putting the lipstick straight on the lips and I usually put a gloss over--just habit and since I got a couple of the holiday sets (which were my 2nd foray into MAC lipglasses, as I only owned ONE plushglass since June 07!) I like mixing it up--putting Twig-Twig on the lips, and covering with a brown lustreglass, or lightening it up with a pinky gloss. I'm terrified of a lipliner and having my lipstick disappear over the course of the day and just have lip liner around my lips. I know you can colour your whole lip with it, but I'm still not sold on it!
Strawbaby seemed to be a bit bright on me (I'm NW15, my mom said it was fine, just that I'm not used to wearing colours other than gloss on my lips!) so I just have to get used to it, test out putting different glosses on top (I like putting tendertones--smells good!) I got High Top yesterday and am going to have to figure out how to get this to work, it looks like itll be a nice one to go out with, I'd almost put nothing over it or a bit of tendertone.
Cantaffordmac, I hear you and I'm still learning! I think there will definitely be some trial-and-error and getting out of the comfort zone (I want to be able to wear colours other than "safe" ones, really I do!) but it will probably just take some time. Hang in there!! At least you know I'm pretty much in the same boat as you!