Have you ever been given a major responsibility and then failed miserably? I’m not talking about small-scale stuff like bombing a physics test or showing up to DMV without proper identification. I mean something that requires lots of preplanning, complicated logistics, and flawless execution. Many years ago, I faced such a challenge, and it turned into one of the worst experiences of my life. It’s a story I hesitate to tell even though, miraculously, it had a happy ending. But getting there was both harrowing and humiliating, and that’s what I want to share here. Maybe what it says about me might reveal an insight for all of us to consider.
After living in New York City for eight years, I needed a change. So I moved to Baltimore and began teaching English at the Park School. Coincidentally, my twin brother got engaged to a woman from Baltimore, and that was where they got married. I was flattered when my brother asked me to be Best Man at the wedding ceremony, although I had only a vague sense of what that role actually entailed. As the day approached, my responsibilities began to materialize. My mom and dad lived just outside New York City, and they were coming to Baltimore with all the guests from our side of the family—seventy-five people in a convoy of buses my mom had arranged for the occasion. That was an impressive feat on her part, but where she erred in judgment was in giving the guests my Baltimore phone number as the contact point for all wedding-related information (no cell phones). That misjudgment really wasn’t my mom’s fault; after all, how could she possibly have known that two days before the wedding, C&P Telephone would cut off my phone service for lack of payment. Had I set out to deliberately sabotage my brother’s wedding, I couldn’t have conceived a better plan.
To appreciate the magnitude of this plot point, you have to consider the situation in context. First, imagine seventy-five wedding guests, many of whom had never been to Baltimore, trying to figure out where to be and when for the slew of events leading up to the final ceremony—everything from a professional photo shoot at the Inner Harbor to an evening candlelight ceremony at Belvedere Square. Second, imagine all the plans my mom had to coordinate to have seventy-five people transported, housed, and prepped for a wedding that size. And while you’re at it, imagine my mom’s embarrassment when she realized that every time a guest dialed my phone number for information, they encountered a snarky electronic recording informing them that the number was inactive for lack of payment. My mom was renowned for her powers of organization; once, she had overseen an audit of my dad’s medical practice so successfully that the government agent in charge actually offered her a job with the Internal Revenue Service. Here she was on the eve of her son’s wedding (the first of her children to get married), trying to manage an emerging catastrophe entirely not of her making. You may have heard that Baltimore’s nickname is Charm City. For my mom, it became more like the setting from a story by Edgar Allan Poe.
I wish I could report that the canceled phone service debacle was the weekend’s only mishap; unfortunately, there were others, including my late arrival to the rehearsal dinner (I had been out cycling in the county). I also gave confusing directions to a guest trying to get to the Baltimore Country Club; somehow, they ended up at the front gate of Johns Hopkins. If you’re unfamiliar with Baltimore’s layout, that’s like someone in search of the Short Hills Mall driving to Newark Airport. And remember, all this unfolded under my “leadership” as Best Man, an irony that certainly wasn’t lost on my mom, nor the scores of misaligned guests who had made the southern pilgrimage for my brother’s wedding. To their credit, they were mostly patient and understanding, but the more I missed the mark, the more ashamed I felt for my disorganization and ineptitude. It was not a feeling I relished.
Despite all the prenuptial mishap and misdirection, the wedding ceremony itself was perfect. It was a beautiful day, everyone was dressed to the nines, and serving as Best Man was one of the highlights of my life, one of those rare occasions when the joy of the moment and hope for the future flood one’s heart with pure happiness. As I joined the wedding party and guests at the reception, I was in full readiness for a celebration worthy of such an august occasion. And so it was. However, as I circled the banquet hall to chat with guests, many of them said that they couldn’t wait to hear my toast to the bride and groom, especially given that I was an English teacher well known for his command of the language and his oratorical prowess. That’s when it dawned on me that I really hadn’t given the toast that much thought; I had just sort of figured I would wing it, and somehow the words would come out. Suddenly, I realized that I had to stand up before almost two hundred people and capture the biggest moment in my brother’s life. Blowing that would make my phone disconnection pale by comparison. So I ducked out of the hall, locked myself in the coat check room with pen and paper, and gave myself five minutes to make the magic happen. And you know what? It did. Maybe it was necessity being the mother of invention; maybe I was desperate for atonement; maybe I really do have a way with words. But whatever it was, I gave a command performance, received a standing ovation, and finally did something that made me feel both qualified and worthy to be a Best Man.
In a number of my Flex pieces, I have shared some of the worst misjudgments of my life. For the most part, they occurred when I was young. Ran around in a raging thunder storm: age five. Bunny-hopped a downed power wire on my bike: age eight. Grabbed a venomous snake by its tail: age twelve. But my Baltimore Best-Man fiasco? I was almost thirty, five years past the point when neurologists say the brain is fully developed, or as my mom used to say, after a certain point, you should know better. In the immediate aftermath, I felt pretty bad; I had let a lot of people down, especially my family. But over time, I gained perspective on what had happened, and began to see my dalliance as a chance to do better, to become more consistent and reliable, especially for those people who depended on me. Of course, we all try to become better people: we count our steps; we listen to podcasts; we make resolutions on New Year’s Eve. But for me, my brother’s wedding was the key turnaround wake-up call I needed, and in the forty years since, it has remained a potent impetus behind my life’s goal to better serve my family, my students, and my community. And of course, to pay my bills.
***
Author photo by Anthony "Truncs" Truncale '26
To contact the author: Mr. Keating