The Oak Leaf Trail

There’s nowhere you can be that isn’t where you’re meant to be.

-John Lennon


It feels…untimely, I guess, to say that I have less than two weeks left in Milwaukee. I feel like it was just yesterday that my dad and I were driving back to Wisconsin after I took my final college exam, yet here I am, early August, about to leave for law school. Crazy.

For any of you that have ever been to (or are perhaps from) Milwaukee, you may know that the lakefront is a popular place for people to take walks, ride bikes, etc., especially in the evenings after our collective long work days. I’ve taken to walking along the lake at night, listening to music to help me unwind–admittedly, this is in part because I hate running, but I still feel obligated to do some kind of physical activity after spending hours in an office.

Anyway, two nights ago, I embarked on my evening walk after a long day of work. I usually take the same route along the Oak Leaf Trail, a long and winding path that leads throughout the city and lakefront. Heading south as the sun slowly began its descent, I strolled to the melodies of Gregory Alan Isakov and other indie rock artists, savoring the fresh evening air and reflecting upon the time I’ve spent in Milwaukee throughout the past few months.

The path diverges many times, and a fork lay ahead. I slowed my pace while contemplating which way to turn; I had turned right the night before, which led me toward the city. I couldn’t decide if I wanted to return that way, since it had been beautiful, but by the time I reached the fork, I decided to turn left to head closer to the lake. My days left in the city are numbered, I thought. I should try something new.

The music continued to flow into my ears as I ventured closer to the lakefront, observing my fellow citizens walk, sit, reflect, hold hands, roller-blade, bike, run. Suddenly, a familiar form entered my sight. Looking left, I spotted a man talking on his phone. I looked again, and I realized it was my old friend, Henry.

I stopped walking to stare at him, waiting for him to notice me from the opposite side of the path. After a moment, he looked up at me, too, and smiled. There was a bench nearby, so I took a seat and waited for him to finish his phone call. When he did, he met me by the bench and we began to walk.

“How are you, Henry?” I began.

After a pause, he smiled sheepishly and replied, “Oh, I’m doing just great.”

As is usually the case, I couldn’t tell if he was being sarcastic or not. We continued walking before he elaborated.

“I just got off the phone with my dad. My mom…my mom left him today.”

Stunned, I fought to find the right words. Knowing that no words could possibly capture the essence of my remorse for his dad, his mom, him, his family, all I could muster was, “Henry, I’m so sorry. I don’t even know what to say.”

He didn’t either.

Slowly, we continued walking. Periods of verbal contemplation about love and marriage, two things that both Henry and I are far less experienced with than our forebears, interrupted periods of silence. Henry is one of my oldest friends. He was the first boy I ever kissed, the first person I ever called my boyfriend, the first boy I ever slow-danced with. That was years ago–seven or eight, we figured. It takes a seasoned friendship to withstand life’s trials, and I would argue that the ultimate test in determining the strength of a friendship is whether or not two people can walk together in silence, but still feel as though they are communicating with one another. It took several years to get there, but I think Henry and I pass that test.

While we walked, I couldn’t help but think about the last time we had been down by the lake, taking a similar walk when one of us was in crisis. Last time, it was me. In May of 2015, I did one of the hardest things I’ve ever had to do: I called the cops on my parent. My parent had been drunk, and in an act of spite against me, got into a vehicle and started driving. I called 9-1-1 for the first time in my life, and two cop cars arrived at my house shortly thereafter.

This incident marked the beginning of a three-day marathon of my own personal hell. That same parent was taken to the hospital after being under the influence of who-knows-what the next day, and then staunchly refused treatment before walking out of the hospital. My other parent left our house later that same day. Left. I didn’t know if that one would come back or not, but to be honest, that was the least of my worries. It was fight or flight time. I thought about where to send my younger sister, where to send myself, and what to do. But I mostly thought about death as my parent continued to drink, and drink, and drink. I truly believed that this was it. This was the end, and it wasn’t just God that was going to witness it. I was, too.

In the midst of all of this, I sought refuge at Henry’s apartment in Milwaukee. The situation at home had become so toxic, the resolution of my parent to reject all forms of help and to self-medicate had become so strong, that the only thing I could think to do was to leave. Perhaps my parent would wake up in the morning, look around at an empty house, and finally decide that she had arrived at rock bottom. I hoped so, because the truth is that I didn’t know how I was going to go on if things got worse than they had become during the 72 hours of terror that unfolded after I made that phone call. Nevertheless, Henry welcomed me into his apartment for the night, and he listened while I cried. I couldn’t have known that just over one year later, I would be the one comforting him while his family, too, unraveled.

Henry and I aren’t best friends, and we don’t see each other often. There are many things we don’t know about each other, and to be honest, I think there are many more that we don’t even understand about each other. I’ve spent years trying to figure him out, and I’m not entirely sure I have yet. Despite that, though, we’ve somehow managed to find our way back to each other during some of the more difficult moments of our lives throughout the past seven or eight years. He was there to talk to me after two difficult breakups, I was there to talk to him when the woman he loved inadvertently revealed she was sleeping with other people, he was there to distract me from my fear during the summer before I left for Boston, I was there to question some of his rebellious actions shortly after he started college and was free of his parents’ strict influence.

And on this night, the Oak Leaf Trail led me to Henry at the very moment he needed a friend. He didn’t know it, and I didn’t know it, but once again, the universe seemed to have known. Every occurrence, every action, every impulse before the moment I laid eyes on him had to have happened as it did for me to quite literally be led to Henry the day he found out his parents’ decades-long marriage had come to a screeching halt, and as we walked, and talked, and didn’t talk, that’s all I could seem to think about.

It’s funny, because before I said goodbye to him when he dropped me off that night, I asked Henry if he thought it was weird I had run into him when I did.

“It does seem like kind of a coincidence, I guess,” he replied.

“Does it?” I asked.

Henry didn’t seem particularly captivated by the timing. We live in the same city, after all. It was bound to happen eventually. Right?

I’m not sure if I believe that. There were approximately 230 students in my high school graduating class, and I would estimate that roughly one quarter of them–and that is a pretty conservative estimate–now live in Milwaukee. I live in one of the “trendier” neighborhoods, one not lacking recent college graduates and young professionals. I frequent bars, restaurants, grocery stores and walking trails throughout the city, and I have run into exactly one person, other than Henry, that I knew prior to moving to Milwaukee. It was a girl named Sarah that I had sung with in high school, and I only caught a glimpse of her when she walked into a bar one night.

I’m not trying to grasp for straws here, I’m really not. Maybe this all was a coincidence. Maybe this really wasn’t that weird, maybe it really was bound to happen. As Henry pointed out, we do live in the same city, after all.

Despite those facts, though, “coincidence” doesn’t seem to encompass it all. “Coincidence” doesn’t seem to explain why I had never run into him before, at any other time or place, despite the odds of theoretically doing so always being the same. Aren’t the odds of running into him the same as those of running into anybody else I know, too? If so, why him, why then and there? Maybe his proximity to me increases our odds. I don’t know where everyone else I know lives, exactly. Some undoubtedly live farther away, but it’s more than feasible to suspect that some live just as close or closer. And besides, if the odds of seeing any one person aren’t exactly the same due to differences in geographic proximity, wouldn’t the odds of seeing Henry be greater than the odds of seeing somebody else that lives farther away? As in, wouldn’t the supposed inevitably of this happening also suggest that this would have or should have happened sooner or more frequently? Even barring that fact, the exact point of our meeting was exactly 1.5 miles away from my apartment, and roughly the same distance from his, in an area of the city that is frequently populated by people from all over Milwaukee. It wasn’t at the grocery store a few blocks away, it wasn’t while I was walking or driving past his apartment, it wasn’t at a bar in between our two residences.

If we’re going to boil it down to logic or logistics or technicalities, “coincidence” isn’t the right word. If anything, “probability” is. But, of course, I didn’t start this blog to ponder the manifestations of probability in the everyday lives of human beings. I’m neither a mathematician nor a statistician, so I’m not qualified for that, anyway.

About a month ago, I published a post titled “Torpor,” wherein I silently entreated the universe to send me a reminder that things really do happen for a reason, that hidden within the monotony of life’s everyday moments lies just a little bit of magic. Only a few weeks after posting that, here I am, posting about this “chance” encounter with Henry. Once again, our paths crossed during a time of turmoil–but this time, the turmoil was within both of us. We were both heading down the same path of The Unknown, and as coincidence, or probability, or luck, or something else would have it, we were also both heading down the same leg of the Oak Leaf Trail. For just a moment, after all of these years, we both got to support each other along the way, and we reunited at a time when we both needed to know that hope awaits just ahead of the curve.

This is particularly meaningful to me here and now, as I prepare to embark on the next leg of my journey to and through law school. I’ve prepared for it for years, and I’ve spent the past several months planning for it. I’m a planner and a preparer by nature, and I used to get so unbelievably anxious when things went wrong. But there’s something about everything going wrong that makes you stop to think about planning a little bit differently. It all fell apart so quickly for me, and as I have continued to rebuild different parts of my life throughout the last couple of years, I’ve continued to understand a truth that I somehow couldn’t see for so long.

It’s so easy to get lost in our plans. It’s so easy to lose faith and hope and trust in things because we are taught to rely on logistics, and technicalities, and probabilities to tell us the truth, to tell us what is possible and what is not. But there’s something about not planning, about trusting whatever part of our gut tells us to turn left at the fork, and everything going right–maybe even more right than we could have prepared for–that gives me hope that something else decides what lie ahead. It gives me a hope that is happening every day, this hope that I can’t always see, but which is always weaving in and out of every movement, every action, every decision I make.

And as I walked with Henry along the Oak Leaf Trail, it is this hope that led the way.











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