The 30-Year-Old Regret That Keeps Me Up at Night

One thing I was surprised to learn in the years since I turned 50: You can never really leave the past behind. At least I can’t. Sometimes when I have trouble falling asleep, I think about the innumerable things I regret and my thoughts inevitably turn to Michael, who, 30 years ago, was my best friend.
 
Michael and I were about as close as two people could be without having sex. We were both aspiring writers who shared a youthful arrogance that flourished in a world that revolved around ourselves. It was our way of feeling special, our way of setting ourselves apart, and that, in turn, made us even closer. In other words, we were the boy version of Girls.
 
Then Michael met Chloe. And I know what you're thinking. You've heard this one before: Boy meets Yoko, they do the "Titanic" thing, and when the love boat sails, someone is always left behind. But it wasn't that way with us. On the contrary, Chloe and I immediately hit it off, so well that she insisted on setting me up with her best friend. The four of us went out soon after and had a great time. Chloe was so funny (and hot!) that I actually talked to her more than I did to my date. When I called Michael the next day, he could barely contain his rage. "How the hell could you come on to Chloe like that?" he said. Since this happened three decades ago, the details are fuzzy, but I do remember feigning bewilderment, then blaming it on one too many bottles of wine. After that I fell silent, just the way my kids would, some years later, whenever I caught them doing something they shouldn't have been doing.
 
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I let a few days pass before sending Michael a peace offering — a copy of The Catcher in the Rye, his favorite book. I inscribed it with a homily from It's A Wonderful Life — words that the guardian angel Clarence wrote to George Bailey. "Dear George," I began, "no man is a failure who has friends," and I signed it "Clarence." The truth of that line had always sent a small shiver down my spine and apparently it did the same to Michael. After much apologizing, we managed to patch things up.
 
Until I met Caryn, the woman who would become my wife. Suffice it to say, I fell hard. I wanted to spend every waking moment sharing every aspect of my life with her. I wanted us to be as close as two people can get. On one of our first dates, I gave Caryn two books — The Ghashleycrumb Tinies by Edward Gorey and a photo portfolio by Diane Arbus. I was a regular Barnes & Noble back then, but at the time, this gesture was akin to giving Caryn a small piece of me. Needless to say, it was Michael who had introduced me to both books.
 
As the natural order of things took their course, Michael and I saw less and less of each other. It had never occurred to me while we were in pursuit of the women of our dreams that actually finding them would drive a wedge between us. I remember, in one of our last conversations, telling Michael how I thought Caryn might be the one, and he seemed genuinely happy for me. I said something like, "I want the people I love to love the people I love," my pretentious homage to Raymond Carver, and we agreed to get together soon.
 
Only I didn’t know how to love both people that loved me. All the shared experience, brutal honesty and level of intimacy forged with Michael was no match for Caryn’s mere nakedness. We were by then one soul inhabiting two bodies. What did I need a best friend for when I had one lying by my side?
 
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So when Michael called to make plans for the weekend, I came up with an excuse. When he tried to reschedule, I blew him off again, and when we were all supposed to get together for dinner in the Village, something came up. I didn't care that I was lying to him, that I was hurting him, that I was cutting him out of my life. My life was suddenly quite full, thank you very much, and there was no longer room for Michael.
 
I like to think that everyone leaves a friend like Michael behind as they move from extended adolescence to something resembling adulthood. That friendships, like milk, have expiration dates. That what splits people apart is just as mysterious as what brings them together. I like to think these things because that way I don't have to face the shame of twice betraying an important friendship. First with Chloe, then with Caryn.
 
It has been several lifetimes since Michael and I last spoke. Every so often, I've been tempted to call, but another remnant from the past stops me cold. A few months after Caryn and I moved in with each other, I received a letter that still makes me squirm. In it, Michael crucified me for my betrayal of him. His brilliant finishing touch was throwing my own Capra-esque act of contrition back in my face, twice underlining "No man is a failure who has friends," exposing how empty those words were. 
 
As we get older, we like to think we get over the things that troubled us in our youth. As mature adults, we’ve learned from past mistakes and who we were back then isn’t who we are today. And sometimes late at night when I can’t sleep, I like to think that my old friend Michael somehow may have found it in his heart to forgive me.