As a native Midwesterner, it should come as no surprise that I’ve never set foot on a surfboard. So, when my boyfriend bought me a pair of black and white teeny-tiny, surfer-style bikini bottoms, I laughed in his face. Keeping them was my first taboo. My second? Wearing them while on holiday in Portugal (land of tiny male briefs and thousands of miles away from any surfing mecca).
Here we were, swimming in the natural pools of Porto Moniz, a small town on the Northwestern Coast of Madeira, Portugal. This was not a place for fashion swimwear and American surf culture; this was a place for no swimwear, no sunscreen, no Wi-Fi, sketchy public restrooms and razor-weary Europeans smoking cigarettes around children.
I emerged from the locker room bashfully, discreetly picking my tush, only to realize the shorts’ purpose was to give the wearer a permanent wedgie. With my cheeks flying free, I scanned the rocky crags to find my boyfriend lounging in the center of the action. “Let’s take a dip!” he cried, grabbing my hand and pulling me in the direction of the diving board that dead-ended with a 30-foot drop into the Atlantic Ocean.
Mind you, I wasn’t exactly feeling light as air that day, nor was I feeling confident about my derrière after the previous week’s lineup of carbs, chocolate and lots and lots of white wine. But o.b.® tampons made me feel confident (along with my boyfriend’s cheers from the back of the diving board line), so I took a deep breath and then a deep dive into the cool waters below.
It was exhilarating. As I followed the beam of sunlight to the top of the frothy sea, I couldn’t care less what my fellow tourists thought of my out-of-place outfit. I was on holiday! It was highly unlikely I would ever be in this beautiful place again in my lifetime and I made a promise to myself that I wouldn’t waste any more of my time worrying about wearing, saying or doing the wrong thing. I felt confident and empowered to take more risks – both in the sartorial sense and when it comes to diving headfirst into challenges.
Whether it be donning itty-bitty board shorts, trying the latest beauty trend or setting up front row in a new fitness class, living your life to the fullest and not caring so much about what other people think are two MAJOR must-dos.
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