I once won a Halloween costume contest by accident. I was wearing an inflatable costume that made my skinny frame look like it was carrying an extra 250 pounds. Right before contest kick-off, my friends got thirsty and I got nominated to fix the problem. But as I waited in line to order a drink in the tiny, narrow college town bar, I got pushed up against the back wall and counted as a contestant. I barely noticed I was even being considered until someone announced “THE FAT BOY” as first place and handed me a $100 bar tab.

A few years later I realized on the day of All Hallows Eve that I had never found a costume with which to parade around in that evening. I headed to a decimated Wal-Mart costume aisle to find only a single dinosaur costume left – and it was clearly meant for someone who had yet to complete third grade. I ripped at the seams, shoved it over my head and made the most of it. (It was also the day I’d asked my girlfriend to marry me, so in most of the photos, my giddy smile outshines the goofy choice of apparel.)

As I’ve gotten older I have gotten a little more hesitant to fully embrace Halloween costuming. I once optimized my short blonde hair and a friend’s blue scrubs to do a low-maintenance Nurse Jackie impression. Another year I bought a $6 red t-shirt imprinted with Bill & Ted’s Wyld Stallyns logo and carried around my Guitar Hero controller. One time I even stooped to buying a fake mustache and pretending to be my dad, circa 1976. (My dad did not think this was funny – AT ALL.)

Now I have kids to carry the costume torch. They mostly enjoy impersonating characters and imagining themselves as superheroes these days, but I hope someday soon I can convince one of them to try on that inflatable costume that won me all those drinks so many years ago. It is still packed in the garage, and the last time I tried the switch on the battery pack, it slowly whirred to life and caused me to smile.

As kids, Halloween is the one time you GET to pretend to be someone else. As we get older, we often feel the need to be a different version of ourselves on most days of the calendar year, so October 31st just becomes another day of dress up. If there is one thing Halloween is good for, it is remembering how much less you used to care about what other people think and how good that can feel.

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