I’ve always been terrible at fasting. Sometimes I think it’s because for my mother, who began her family life in the Midwest in the 1960s by rejecting her parents’ Orthodoxy, Yom Kippur was mostly about the break-fast. Mom prided herself on being, in her words, “the hostess with the mostess,” and Yom Kippur was her time to shine.So my younger sister and I spent Kol Nidre night helping Mom set out straw baskets and silver platters, every one of them blessed with a white doily. Mom had painstakingly penciled labels—bagels, salmon, cucumbers—so we could be entrusted while she was off at Yizkor the next day to get the cream cheese and blintz soufflé to their proper places at the table.My first attempts at fasting, then, were mostly failures. While Mom was away at Yizkor, it became a game: Who would be the first to succumb? Who would idly slip her finger into her mouth after swiping the cream cheese from its silver foil wrapping to the plate? Who would cut the kugel and slurp from the knife the illicit joy of butter, noodles, and crushed corn flakes?Years later, when I married a young man who lived within the Orthodox community, I was surprised to learn that Mom’s version of the ritual, ending as it did at 4:30, was only part of the story. Carmi’s family began the fast at 4 on the evening of Yom Kippur and didn’t end it until 8 the next night. I had willingly warmed to some of his traditions, on holidays like Shabbat and Sukkot. (A booth built on the deck in back, open to the stars—who could resist?) But I was shocked to learn we would be fasting on Yom Kippur for a marathon 28 hours.Wanting to please my in-laws, wanting to show those in their modern Orthodox community that this young woman who had come from “outside” their world did in fact belong here, I sat, on our first Yom Kippur together, eagerly awaiting my mother-in-law’s pre-fast meal. As I dug into what seemed a meager offering—a baked potato, a chicken breast, some melon—fortifying myself for the ordeal ahead, my soft-spoken yet also Israeli mother-in-law said, “Your fasting will be easier if you don’t overeat.”She was advocating a kind of restraint I was unfamiliar with, having been raised by a mother and father whose worldviews attended to no higher authority than their own. My mother-in-law, though, had begun her fasts at the side of her Hasidic father in Jerusalem. I had only begun to discover the spiritual nourishment she had tasted and was hinting at.The next evening, 200 of us gathered for Neilah—the service that ends Yom Kippur—in a small shul tucked behind a Dunkin’ Donuts parking lot in St. Louis. My stomach felt painfully hollow, and there was a vast airy feeling in my head that rendered everything slightly off kilter.The stern, goateed rabbi, who had studied under Rav Soloveitchik, said that the first mournful notes of the Kol Nidre melody we had heard the night before speak about convening a Beit Din, a rabbinical court. The Hebrew words are a legal formula, he said, giving us all permission to pray with the avaryonim, “those who sin or transgress.” At 24, it was hard to imagine myself loaded down with the weight of sins, and all day, as we had recited them, there had been some inner resistance to this list. I was the dutiful daughter, the student who sat in the front row and earned A’s. If anything, it was easier to recount the various sins others had committed—against me.But the rabbi pointed out: Not only are we permitted to pray with sinners, we are required to. Why? Why are we Jews called to this difficult exercise? I didn’t yet understand the depths of the soul work I had stumbled onto, but now that we had all spent some 20 hours fasting, a good six long ones in shul, something within began to shift. On this third time going through the list, the al chets, reciting and naming all the tiny everyday ways we human beings manage to err, I realized that the repetition of the words had opened a space within where I might begin to own some of the ways I had messed up.I stared at the right side of the prayer book, the Hebrew letters my husband and all the others could read, as they began to sing. This melody came a third time as well, an odd comfort now. The men rocked and chanted as we women mostly stared at them over the glass blocks of the mechitza. I still resented that mechitza, but somewhat suddenly, I was caught up in their song, like a vast wave you resist at first that takes you anyway.Grown men, bearded and not, called out to some unseen presence, crying as I’d never heard men cry before. They stamped their feet, full-throated, saying something that sounded like, “Mommyrecha.” Though many of them were old and grizzled, you could hear their yearning—for life, for help, for comfort. It was something I felt in my emptiest places, not unlike that of a child calling out for its mother, something that lingered.*Eight years later, my young family and I left the Orthodox world—its mechitza and the paltry roles for women, even a certain adherence to the letter of the law without a strong enough regard for the law’s spirit, drove me out. And though we held onto the holiday cycle, every year I went into Yom Kippur with some resistance.Belly empty, head aching, I was still telling myself that someday I might master this fasting thing, not have to experience it as quite so difficult. And sometimes, in the ballroom of a hotel our temple had rented, I would find myself returned, in the final repentance moments, to the cries of that white-kitteled sea of men in the shul behind the Dunkin’ Donuts. The sound of their yearning.Last summer, my 59th, I had a strange prelude to the holiday. Call it an involuntary pre-Yom Kippur fast; due to a mysterious illness, I had suddenly lost my appetite and in two weeks, dropped 20 pounds. Weakened and shaky, I could barely manage a walk to the muffin shop on our street corner in New York City. Sun-filled days had been taken as well, as the doctor who was looking into a possible thyroid problem had prescribed beta blockers and said to stay out of the sun.Without a real diagnosis for weeks, it was an anxious time, a time for pondering life’s essentials, for feeling closer than ever before—to death.So when Yom Kippur rolled in last autumn, I listened at a shul in the West Village as a rabbi friend with a decidedly mystical bent blessed all of us toward the end of the Kol Nidre service. We were in a school basement turned synagogue, with a tableau of white roses at the center and a small band of musicians—oud, violin, tabla—on the left. Moments before, the violin had cried out the Kol Nidre melody—and I had felt the weight of being among the avaryonim. Not necessarily sinners, but broken. Something broken in each of us called forth.Rabbi Jim Goodman knew the heartbreak sound of the Kol Nidre. His 30-year-old daughter had died the previous year, and it was his first Yom Kippur without her. Despite this, he was upfront, singing to us and offering a blessing. “May the Lord bless you and keep you,” he chanted, “May her soul shine upon you.” His daughter’s presence was there, behind the words.Only five hours into this latest fast, I had a kind of vision, feeling not just the meager slant of a streetlight coming through the window, but some greater light, some graceful slant of blessing that might be possible. I remembered a day that summer, the first day when I finished the beta blockers, and had slid into a cold pond in Wellfleet, Massachusetts. After swimming a few laps, I had turned my face to the sun and felt its warmth, like a blaze. I had my life back.During the days leading up to the holiday, I had reread Alan Lew, whose approach to Yom Kippur is there in the title of his book: This Is Real and You Are Completely Unprepared. Lew sees the High Holidays as “a great crossing.” He writes: “There is nothing behind us, and nothing ahead except this narrow bridge, and beyond that only a great wind, that same wind the psalmist saw, that wind that will come by the moment after we have withered away like grass, when no one will even be able to see the place where we were.”After all these years of fasting, I had begun to understand the wisdom of Yom Kippur as a rehearsal for death. No eating, no bathing, no sex. Don’t do anything to mar the illusion that you are dying—which is true for all of us. Someday you will have to give it all away—your very life—and perhaps it will be easier and better if you practice that now.So I was in a more accepting mode and less resistant the next day, as I took my seat for the closing service in yet another prayer place on the Upper West Side—a church basement turned shul. I was OK with sitting in the emptiness, and the hunger, too. Noticing the yearning—not just for food—for everything that awaited on Amsterdam Avenue and beyond.Lucky me, I happened to be seated by a friend who spends vast hours of his life in meditation. When the congregation rose for the fourth Amidah, the standing prayer—the last—Larry stayed seated. I rose to join the others and then, with my own paltry version of a meditation practice in tow, figured out I could join Larry.Would I be ducking out on the ritual? The Young Israel community I had left behind in St. Louis, those men shuckling in their kittels, would definitely say yes. But then, maybe reading the prayer by rote, forgive us for this, forgive us for that, was in fact the “lazy” response. Maybe plunging into whatever depths awaited within was the harder thing, and braver.So I sat, closed my eyes. Intent on doing nothing but noticing whatever arrived. And breathing. Someone coughed nearby, the air conditioner hummed. An ache in the belly, a near painful wanting of food, a headache only coffee afterward would cure. A body washed through with all of the imagery and words of the day, including “Al Tashlichaynu”—Do Not Abandon Us—sung by our woman chazzan, a friend who had prayed for a decade for a child and this year, had one. The way her voice rose and reached across whatever bridge or ladder we are suspended upon, into something transcendent, into the deepest reaches of faith and love.As we all sat in silence together, just before the last notes of the shofar blast came, I felt two things at once. The vastness of being empty, all the disparate pieces of my life—the grown children, off and forging their own young adult lives, the radiant light of a first and only grandchild, my father who came through open heart surgery this year, the rabbi friend whose daughter’s life was taken, and a husband whose pains and joys have become my own. All of it swirling within me, and all of it seemed somehow more possible to hold than it had been before.And also, the vast yearnings of those sitting around me, all of us dying, all of us living, in spite of the chaotic times and this broken world. We are the avaryonim, incomplete and imperfect, but taken together, into the next year or wherever we may or may not go, more than enough.I doubt the Orthodox men back in St. Louis would understand. Certainly they would grimace at the version of Judaism and fasting I am living now. But it is something my mother-in-law, no longer with us, seems to have known when, erev Yom Kippur, she told a young woman not to stuff herself, to turn instead toward the emptiness—and the yearning.***Like this article? Sign up for our Daily Digest to get Tablet magazine’s new content in your inbox each morning.