Finding Magic in the Dreams That Didn’t Come True


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“Most of us have two lives. The life we live, and the unlived life within us.” ~Steven Pressfield

I was born a decade too late in 1975 in a small Pennsylvania town. By the time I was old enough to buy a record, the legendary rock and roll culture of the 1960s and 70s was a distant memory. To some, it might have even seemed uncool by then. But to me, a teen in the late 80s, the era of sex, drugs, and rock and roll was everything.

I spent hours writing song lyrics in my flowered journal, watching MTV, and poring over Circus and Rolling Stonemagazines, trying to catch glimpses of the personal lives of my favorite rock stars. I strummed my guitar and pretended I was Janis Joplin. I was a dreamer, obsessed with poetry and music and the romantic notion of traveling across the country to see my favorite bands.

At twelve years old, I took a bus from my small town to Philadelphia to see the band Heart. At fourteen, my parents drove me hours away to see Stevie Nicks. Then, in my late teens, I drove all the way to Ohio and Las Vegas, Nevada to see her again. No distance ever seemed too far to travel for my favorite music.

Back then, I envisioned myself following bands and living a carefree, hippie lifestyle where my only concern was getting to my favorite artist’s next show. And most of all, I dreamed about a concert at Red Rocks Amphitheater in Colorado.

But somehow, by my early twenties, that dream felt out of reach. I met a man, got married, and had a daughter. Our life was filled with routines that were so different from the vagabond life I’d envisioned for myself. I traded spontaneity for discipline and gave up my dreams of traveling for the security of a stable life and a house in a good neighborhood.

Eventually, the responsibilities of marriage, career, and never-ending to-do lists made my dream of going to Red Rocks feel more and more like only that—a dream.

And it went on like that for seventeen years. Then, after years of doing what I thought I was supposed to do, my husband and I decided to separate.

I embarked on life as a single mom. And as I did, I reflected on the last two decades. We’d married young and, in retrospect, I realized we probably weren’t a good match. He was a real estate attorney with a strong personality and even stronger opinions. I gave our marriage the best of me that I could, but it felt like I was always being who he wanted me to be.

I had lost myself. I’d lost sight of my own hopes and ambitions. I’d never even made it to Red Rocks.

In 2016, newly single, I felt eager to date again, so I downloaded Bumble and set up a profile. Not long after, I matched with Jerry. He lived on the West Coast but was in my hometown of Philadelphia for a Dead and Co. concert—the same one I had tickets to.

Jerry had told me he’d followed the band as a teenager, but he hadn’t stopped going to concerts like I had. He’d held onto his dream and seen them at least 500 times. It was almost like he’d lived the life I’d imagined for myself way back when. We seemed to be kindred spirits. But I had a type, and that was someone who was within a fifteen-mile radius, so I decided not to meet up with Jerry at the concert, despite being intrigued.

Jerry and I kept in touch over the next four years, although I never held out any hope for anything more. He was a divorced man with children, on a dating app; I assumed he’d meet somebody close to home, and I’d eventually stop hearing from him. But to my surprise, he reached out periodically, often to talk about what was happening in the world of Grateful Dead concerts. It seemed he wanted to stay on my radar. He was always polite and respectful, never creepy or pushy.

Jerry was ten years older than me, but somehow reminded me of my younger self. He had a refreshingly youthful spirit, which was completely different than any man I ever dated. Like me, he had a corporate job, but he didn’t let that stop him from following his band across the country. Music was a huge part of his life, like mine.

We kept in touch, and by the summer of 2021, the pandemic restrictions had started to loosen. Outdoor events resumed. I’d been itching to go to an outdoor concert, and that’s when Jerry told me he had an extra ticket for Dead and Co. Honestly, when I accepted the ticket, it wasn’t to finally meet Jerry in person. I was just tired of being stuck at home.

I didn’t have any expectations. But the first time I saw Jerry smile in person, I had this feeling my life was about to get a lot more adventurous. And I realized I liked him. He was intelligent, polite, and handsome, and he loved all the same music that I had loved for years.

After that first concert, Jerry told me he was falling for me and that he wanted to see me again on his travels with the band. When I reminded him that I was a single mom with a full-time job and couldn’t follow a band, he offered to take me to Red Rocks for my birthday.

I couldn’t say no. Jerry was handing me my childhood dream on a silver platter, and I wanted to eat until I was full.

He pursued me relentlessly, and it was exhilarating and romantic. Nothing like that had happened in my adult life before him. We spoke daily, and our adventures over the next two years were amazing.

But about two years into our relationship, I began to realize that Jerry and I might not be forever. We led such different lives. His was wild and interesting; mine was more predictable. And as much as I loved his spontaneity, I began to see how chaotic his personal life was. I started to wonder: Was I in love with Jerry, or was I in love with the way he had stayed connected to his childhood dreams as an adult?

After two years of seeing each other periodically and talking daily, the facade started to fade. The rose-colored glasses were off, and I was seeing things more clearly. While professionally successful, Jerry jumped from job to job. He lived in constant drama with his family, and all his traveling took a toll on his health and his relationships. I also started to wonder if there were other women like me in his life.

I never doubted that Jerry cared deeply for me, but I couldn’t help but wonder if he had women like me in several states. I never asked him. I wanted to stay in my bliss, living out my childhood dream of music and love—to stay in the bubble of contentment and happiness with what we had, with one exception.

I wanted to see more of him. And, ultimately, I wanted to know that I was important to him.

Jerry couldn’t do that. He had a hard time committing to anybody or anything other than the band. I understood. It was that lifestyle that drew me to him in the first place, but I couldn’t continue a relationship like that.

The last time I saw Jerry, as I was dropping him off at the airport to fly home, I started to cry uncontrollably. I realized that the free-spiritedness of dating Jerry had a dark side: uncertainty. Every time he left, I never knew if or when I would see him again. Like the bands I had loved to follow, everything was on his terms. He decided when, where, and how, while I just showed up. It was incredible, but I wanted—needed—more.

When I told Jerry that I wanted more commitment, I thought for sure that he would choose me. It’s what I would have done. But he didn’t. And it broke my heart. At least for a while.

Once my relationship with Jerry ended, I had time to reflect. I realized that in our pragmatic world it’s all too easy to exist on autopilot. Still, we shouldn’t abandon our childhood dreams because they connect us to our inner truth and reveal the magic that surrounds us—and not only in iconic destinations like Red Rocks or in grand gestures like love-bombing and being swept off my feet.

Magic also exists in the beauty of a cotton candy sunset while driving home after a long day at work. It exists in the time I spend with the people I love, like my ninety-year-old mother, whose short-term memory no longer exists, but when we sit hand-in-hand and play Frank Sinatra’s “New York, New York,” we smile and sing every word and feel joyful in the moment, even if we’re off-key.

Magic surrounds me when my ex-husband, who I consider a friend now, and I watch our magnificent eighteen-year-old daughter live her life, and beam with pride at the amazing young woman she’s become.

Most days, though, I find that when I listen to music, attend concerts, and spend time writing, those are the moments I know who I am, and my childhood dreams come to life.

And, of course, falling in love with Jerry taught me a valuable lesson:

Relationships don’t have to be long-lasting to be impactful. Sometimes, a short-lived experience, like those concerts I chased all my life, could contain years-worth of depth, love, and meaning.

And, I learned, dating doesn’t have to lead to a ring. Sometimes it leads to living a childhood dream and falling in love under a clear Colorado sky.

Sometimes, that’s enough.

About Shelly Gill

Shelly is a sales professional and occasional writer based in the Philadelphia suburbs. She’s passionate about storytelling, good music (especially sixties rock and roll), and having fun to the beat of her own soundtrack.

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