On Biking in Chicago & Healing from Heartbreak

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We weightlessly drifted through the red light, our street bikes gliding like paperclips across Chicago’s potholed street. I haven’t written much about this season of my life because I always seem to drift back to 2007, the golden summer of my life.

But those days riding around Chicago warrant their own reflection a well. Not only were we as free as birds, but the speed made us feel alive. We raced buses up and down Michigan Avenue — The Magnificent Mile — and tourists would stare from the sidewalk, agape at our brazen (stupid?) way of riding.

We never wore helmets.

For three years, I somehow avoided death and even minor accidents, as the worst thing to ever happen to me on a bike was the occasional butt cramp. My friends and I rode like idiots: We weaved in and out of the city traffic and cut in front of expensive cars. In those moments, however, we were more free than the millionaire in their Land Rover who was stopped in the long line of cars.

Biking in the city is perhaps the most freedom a city-dweller can experience. You’re not bound by bus and train schedules, nor are you restricted by red lights or urban congestion. These, on top of the fact that you’re saving the environment, pumping out your quads, and bla bla bla.

The reason I haven’t often explored this season of my memory is simple: I was heartbroken. Even though the biking was exhilarating and my body was in peak condition, my heart was shattered. I suffered a crippling rejection from a beautiful girl at my school which tainted the following years. I often rode to forget her. This was ironically difficult because she was an avid biker, so the more I rode the more I thought of her.

She was cool.

In every sense of the word, she was hip. She was up to date on trends of every stream; she was interested in everything, and could talk to anyone about anything. She was a hard worker and was funny. And she loved to bike around the city too.

Now 5 years removed from that episode, it stings less but the wound remains. Why did her rejection hurt enough to taint multiple years of my life? We had been best friends for our first two years of college. We did everything together, but only as friends. Two years later, a light switch flipped in my brain and I realized she was the greatest human being I’d ever met.

But by then it was too late. She has friend-zoned me and intended to keep me there. It was possibly the first time I had become attracted to a person as a complete entity. I wasn’t just drawn to her hair or her eyes, but her personality and humor. Her drive and her interests. Basically everything about her. Of course as a consequence, whenever I saw another woman with her hair I was instantly drawn to her. The external, visible allure followed the invisible allures.

So I biked around the city to try to forget her. No matter how fast I rode, I couldn’t escape her rejection. I couldn’t escape the feelings of inadequacy or of letting her down in some way. And in many ways, I’m still reeling from that singular rejection.

It’s hard not to let massive disappointments like that define us. Sometimes it takes intentional returns to seasons like them to reason with our past selves and heal the wounds. So that’s why I’m writing this now. I’m not in Chicago anymore, nor am I still biking. But I’m still trying to escape the weight of that rejection. I’m still learning how to heal from that wound — and every subsequent wound.

I’m not navigating city streets on my Grand Prix anymore, though I wish I was because it was a lot easier than navigating this unstructured post-grad life.


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