About thirty years ago I drove my aged mother from her home in Hampton Bays on Long Island to a hospital an hour away in Port Jefferson. She wanted to visit her eighty-seven-year-old younger brother. It was a pleasant drive, but she was quiet because she was worried about him. When we got to his hospital room, we were shocked to see that he was already zipped up in a black vinyl undertaker’s bag. When a nurse offered to open it for a last look, my mother declined, and we went out to a stairwell landing where she began to cry. Through her tears, she kept saying, “Now I’m all alone!” Her two other brothers had died years before, and while she had obviously grieved them, the intensity of this grief seemed much greater and her sense of isolation profound.

At the time, I could not understand. She still had my father, her adoring husband of over sixty years, and she still had me, her only child, whatever that was worth. I could understand her grief because my uncle had been the brother most beloved, but I couldn’t understand that sense of isolation, that “Now I’m all alone!”

I am beginning to understand. My mother and my uncle had a history together from childhood to old age that was, by then, exclusively theirs. They had grown up under difficult circumstances in a very close Brooklyn Irish family with spinster aunts and bachelor uncles in residence as well. They had stayed close as young adults, as married couples, parents, and aging friends. They had summered together in Hampton Bays for years and then settled there in retirement. The rest of us knew bits and pieces of their shared lives, but only they knew it from the start. They had a history together that no one else shared, and, when my uncle died, my mother’s childhood in a sense died with him.

I am facing a similar loss now. My best and most long-standing friend is approaching his end. He suffers from no specific malady other than prolonged bed rest as he waited for two fractured vertebrae to heal. But in that process, his muscles so atrophied that his legs are now just long bones and knobby joints covered in skin. This man who could talk endlessly in leaping conversational shifts and could intimidate waiters and waitresses with his formidable bellow can barely whisper a few coherent sentences.

My parents are long gone. I have no siblings or any cousins left who know my childhood well. My friend is my “knew him when” friend. We’ve been eating and drinking together for almost seventy-five years if you count milk and cookies.

As he tells it, one day, when he was five and I six, he was languishing on his living room couch in his policeman’s uniform when he heard a great commotion and screams of pain outside. Grabbing his rubber billy club and policeman’s hat he rushed out to find the local bully jumping up and down on my spine. Somehow, he rescued me from paraplegia, and I have been in his debt ever since.

We were neighborhood kids on the northern border of Richmond Hill, Queens, the borough that always gets short shrift both in the literature about New York and when the City plows out after big blizzards. (One of the blots on its escutcheon is that it gave us Donald Trump.) Richmond Hill was then solidly white, middle to lower middle class, mostly Catholic and Protestant, and mostly German and Irish. My friend, however, was a Congregationalist. Although he has a pedigree on one side that can be traced back to the Puritans and is the grandson and great-grandson of formidable Congregational ministers, my friend’s religious upbringing seemed less burdensome than the grim Irish Catholicism in which I was raised.

We began in the same small public school in Richmond Hill, but when P.S. 51 ended at fifth grade, we diverged onto separate academic paths: he to another local public school, a local prep school, Princeton, and the Yale Law School; I to an awful Catholic grammar school, an excellent Catholic high school, Notre Dame and the Columbia Law School. (It is worth noting that out of two classes, each of about thirty boys and girls, I know of three boys who went to Harvard, Princeton and Dartmouth. I went to Notre Dame, and three of us went on to Ivy League law schools. There may have been even more. Not bad for a piddly oaky grammar school in a middle-class neighborhood in Queens.)

But we didn’t live in each other’s back pocket. High school with its intense academics, lots of homework, extracurricular activities, and for me a daily three-hour round-trip commute drew us into separate worlds. Our colleges too were distant and different experiences, but we always seemed to circle back to see how the other was doing. During college vacations while we still lived in the old neighborhood, we would take the IND subway to Manhattan to ice skate in Central Park, to trace Dylan Thomas’s staggering steps through various watering holes in Greenwich Village, but mostly to enjoy being in each other’s company. We were more explorers of the city than its denizens at that point. During one New York blizzard, we found a bar/restaurant in the Village that had amateur opera. On another night of wandering, we found a really neat bar with a ceiling covered in black fuzzy mold. Only recently did I discover that “Dirty Julius,” as we called it, was one of the preeminent gay bars of the closeted years. How could we have missed that?

After our post–law school military service, he as an enlisted man in the reserves, I as an officer in an infantry battalion in Germany, we both began our legal careers on January 2, 1966, in separate Wall Street law firms that happened to be located on different floors of the same building in lower Manhattan. And that first day and for the week thereafter, we walked together across the Brooklyn Bridge to get to work because Mike Quill had pulled his bus and subway workers out on one of their long transit strikes.

One winter afternoon, he saved my future marriage. I had taken him and my then new girlfriend on a hike on the Shawangunk Plateau in upstate New York. I had done a bit of serious winter hiking, but this was intended just as an excursion. We were not equipped for any real challenges. The snow turned out to be knee deep in many spots along the trail. Somehow, I managed to get turned around, “just a little lost” as they say, and as the sun set and the dusk deepened, his mantra became “only a mile or two more.” He was tall and a bit gangly. He joked and pranced about in the deep snow waving a long dry reed to distract my girlfriend from the seriousness of our situation while I tried to figure out how to get us back to the car safely. A year later, he was my best man, and a year after that I was his. (His wife is our younger son’s godmother.)

I have no doubt that one of the factors in our long friendship, as probably in most long friendships, has been proximity. In the beginning we lived across the street from each other. After that, for over twenty years, Manhattan was our venue and even later it was our locus when we moved out of the city to nearby suburbs and the outer boroughs.

Another was long bachelorhoods in a very male world. While other good friends were sucked soon after college into the vortex of marriage, children, careers, and suburban commutes, we and a number of similarly educated and inclined bachelors wandered about the city together or separately, dining, drinking, and talking, always talking. It was a pleasant existence: responsible and challenging jobs which often extended into the night, active social lives, solitude in our apartments when we wanted it, and conviviality on the streets and in the pubs of Manhattan when we didn’t.

Another factor was our liberal educations. Neither we nor our friends were professional intellectuals, but each of us had enjoyed four-year dalliances in our chosen liberal art. As a run-of-the mill English major with a tendency to writer’s block, it was clear I would be totally unemployable upon graduation. Although my friend had a degree in economics from Princeton’s Woodrow Wilson School, I doubt his prospects were much better. To make a living, we needed professions. By happy circumstance, we both chose the law, but, being humanistically educated, we were never just lawyers. We were readers and noodlers as well, willing to exchange ideas and to delight in the disclosure of obscure facts in wide-ranging discussions.

For example, a few years ago he was lamenting his frustration that members of his history book club seemed unacquainted with an ancient naval battle whose name he momentarily forgot. I piped up that it was probably the Battle of Salamis, where an outnumbered Athenian fleet, through superior tactics, destroyed a much larger invading Persian force. We went on to discuss the tactics and reasons for the Athenian victory and its ultimate impact on history.

Long friendships mirror in many respects good marriages without the irritations of intimate daily contact. Friends can select the time and place to meet. It’s not over the Wheaties every morning. But since, whether by nature or nurture, men are emotionally constrained and seldom unburden themselves or expose their vulnerabilities, lengthy male friendships require great restraint and sensitivity. One follows up occasional opaque personal comments at the risk of learning too much, and of creating residual resentments which can slowly erode the bonds of friendship. Thus, even though we knew most of each other’s principal successes, failings, and insecurities, regardless of our opinions, we never delved too deeply, nor did we criticize, make strong recommendations, or give advice. We listened sympathetically to whatever the other felt impelled to disclose about personal problems, family medical issues, and lost friends and relatives, but we left the active advisory role, unless solicited, to good therapists. And there was as well an unspoken commitment to confidentiality. What was disclosed went no further.

The real pleasure in our meetings was the conversation. Literature, politics, and history were our preferred métiers, but how could we fail to gossip too. It was like quaffing fine wine in small sips.

For the past twenty-five years, whenever one of us became parched for the other’s company, we made the three-minute call to set up a lunch date at various restaurants on the East Side of Manhattan from Delancey to Ninety-Sixth streets. In prior years a good meal, a few glasses of wine in an unhurried, quiet venue where we could sit and talk to exhaustion, was often followed by a stroll through Central Park. Once, in our late sixties, he shamed me into a few rides on the Central Park carousel, two old men in overcoats going up and down on wooden horses, a throwback to our childhood rides on the Forest Park Carousel in Queens.

As we became old and sadly diminished, however, one of our favorite spots, an elegant art deco restaurant in Midtown, became too far away for my friend. Since he now had an apartment on Fifth Avenue in the Nineties, we settled on a small local French bistro which had excellent food and just a few outside tables. I usually got there first and watched him dotter over to the table on painful feet. The thirty-year-old who danced and pranced through the Shawangunk snows was unsteady now and used a cane. I have enough pipes in my heart to open a plumbing supply store. But, when we sat together at an outside table in forty-five-degree weather, all that fell away. The sidewalk in front of us was very active: women pushed strollers or walked young children by the hand; dogwalkers with their packs of pooches passed; older East Side couples strolled by. There are a couple of expensive private girls’ high schools in the vicinity, so as we sat outside in even the coldest weather, there was a steady flow of young future ladies-who-lunch passing our table. Already slaves of fashion, they’d hiked their uniform skirts so inappropriately high they risked fanny frostbite for the sake of style. As we noted this passage of upscale humanity in all its diversity, youth, and beauty, we two aging boulevardiers commenced another two hours of conversation that ranged over friends, relatives, the current political situation (moan), and, even after fifty years, the poetry and prose of Dylan Thomas, but this time in much more respectable surroundings.

Many friendships, no matter how close at one point, peter out over time. That some have an expiration date is inevitable. People grow up, move away, begin to focus their attention elsewhere, become boring, or are offended by some well-meaning or careless comment. The reasons are infinite and the results unfortunate if a residue of resentment develops and the split widens. Very few friendships last a lifetime. But this is one of them.

I truly love my friend. When he goes into that black vinyl bag, all that history, that continuum we share, will be gone. There will be no one left who knew me as a child, then grew with me over the next seventy-five years. Like my mother so many years ago, I too, despite a loving spouse and caring sons, will be bereft and “all alone.”