How Do I Find My Inner Red Lipstick Chutzpah?

Confession time: I have a weird phobia surrounding bright lipstick. I used to read the online worries of other women who were too fearful to go out in public with a bright red lip and feel smug in my refusal to to get caught up in such petty hang-ups (I know, rude), and now here I am, feeling exactly the same way. I’ve read all the tutorials about the perfect red lip, bought favorite colors, and even got a kickass lip primer — and then proceed to only bust them out once every few months. No matter how delicately and perfectly I apply it, I can’t help but fear that the color is streaking off my lip in bright red globs or caking right off.

I have no problem with shiny glosses or tinted lip balms, but lipstick brings with it a slew of weird neuroses about drawing attention to my mouth. As in, if I have lipstick on that screams “look at me!” my lips better look damn good. I like the shape of my lips just fine, but they’re not super full in that cover-me-in-lipstick way. So does slathering them in Nars just draw attention to that while simultaneously highlighting any odd marks near my mouth? At the end of the day, nobody really gives a damn about noticing the minuscule flaws on our faces, which generally makes me feel free not to care much about it either, but doesn’t that sort of change when your lip color draws everyone’s eyes immediately to your mouth? Could it be the texture that intimidates me? I have lots of red glosses that are a bit smoother than lipstick and I never worry about those looking terrible. I mean, where does my lip end and my face begin? It seems like such a simple thing to discern, but lip lines can get fuzzy and lipstick feels so much more permanent than gloss, so when I apply it I start to wonder if I’ve essentially colored outside the lines on my own face.

Obviously, this is pretty small change to spend time worrying about in the grand scheme of life. And yet! It irks me so! I love the look of bright lips so every now and then I just suck it up and wear lipstick anyway (case in point: the picture with this post), but I’d like to it be more of a habitual thing. I’d love to know your tricks to get over this hang-up, because I’m sure I’m not the only one who’s felt this way. I have a feeling that it mostly comes down to just putting it on anyway and saying “screw it, I’ve decided my lips look fine and that’s all that matters,” but that’s hard! How do you get over the paranoia of looking like a clown? How do you apply the color in a way that actually looks functional but doesn’t take a million years to pull off in the morning? How often do you reapply the stuff without it getting all caked? Help!