Why My 'Bold' Lipsticks Never See the Light of Day

I WHOLEHEARTEDLY believe in the power of a good red lipstick. Did I emphasize that enough by my grammatically incorrect use of capitalization on the word 'wholeheartedly?' My red lipsticks and I have a complicated relationship. I keep collecting them under the pretenses that we're going to be the perfect couple.

Look, they all compliment me when I give them the chance to. I have cool (tbd scientifically) undertones in my complexion so I tend to steer clear from any lipsticks that are too pink. I, along with my wallet, have learned this the hard way.

In the fall/winter when I come across a deep wine/plum colored lipstick, I can't resist. In the spring/summer time, show me an orange hued lipstick and you don't have to ask me twice to take that baby home. But then reality kicks in. The honeymoon phase of the trip home in my Sephora bag ends quickly.

Sure, we can go out together at night when the imperfections on my face are minimized by the lack of natural lighting and everyone around me is not sober enough to realize that there's a Cruella by Nars colored stain on my teeth, AGAIN. But during the day I feel like the glare of the sun is mocking me. You know, in the, "I just love how you wear anything," kind of way.*

Is it a matter of confidence? Maybe it's confidence, maybe it's comfort. The idea of feeling comfortable is much less intimidating, at least to me, than feeling confident is. Each day I get more comfortable with wearing less face makeup (concealer, foundation, tinted moisturizer, etc.). I'll eventually be OK with the idea of wearing no makeup just like I'll be able to silence the annoying thoughts in my head that are telling me I look weird in my red lipstick. That, to me, feels like a goal that I can work towards.

*s/o to John Mulaney's genius brain for that joke