I was a young boy when I first started to observe the custom of staying up to learn Torah the whole night of Shavuot. My first memories are of a few people who drank black coffee and ate cheesecake to fight back sleep in shul. In between trips to the refreshment stand, the learned would horeve over a blatt Gemara—a page of Talmud—with a study partner through the night. But the rank and file, many of them survivors of Hitler’s Holocaust, the plumbers and wallpaper hangers and tailors and grocery men of the shul, listened to Torah lectures from earnest, suited rabbis, before they nodded off early or went home.Legend has it that this custom of late-night Shavuot learning arose to atone for a faux pas, a “sin” committed by our forefathers over 4,000 years ago. A midrash states that on the morning of the Revelation at Sinai, the Jewish people overslept.Yes, the Creator of the universe had called a meeting at Mount Sinai and the generation who had seen the Red Sea split with their own eyes hit the snooze button. They were sound asleep somewhere far from Sinai and Moses had to rouse the people and hurry our forefathers and foremothers over to the mountain for an event absolutely unique in the history of the world: God would speak directly to man. Scripture tells us Sinai was ablaze and its peak enveloped in thick smoke. At this blessed event blind men could see, the deaf could hear, and all the sick were healed. Supernatural and natural became so entwined and mixed up as the voice of God encompassed them that our forefathers could “see” thunder and “hear” lightning.Imagine a bride and groom for whom a dazzling wedding is prepared with shooting stars, comets, and celestial fireworks overhead, yet they fall asleep and don’t show up to their own chuppah. To atone for this, we stay up the entire night of Shavuot—to make absolutely certain we will be there when the episode of the Revelation is recounted in synagogueBefore this event, one dare not go to bed, or even fall asleep even for a little. This year and every year since I was a boy I was filled with apprehension even dread. Would I be able to stay up the whole night? Would I accept the Torah or surrender to sleep?On Shavuot of last year, Chaim, the leader of our small study group in my town of Passaic, New Jersey—a man of infinite knowledge and kindness, whose forehead is so generous that one could swear each of the Ten Commandments in full is engraved on it—prepared an elaborate discussion complete with handouts. He would ply us the whole night with dainty cakes and sweet words of Torah if only we would come. He even put up a tent in his backyard to protect us from the rain that had been promised by the weather service.The topic would prove to be an intricate one, although it begins simply enough: Every morning of every day of the year we bless God for having given us the Torah. What if we forget? Can one study Torah without a blessing? Of course not! Yet the Talmud throws us a rope: Another blessing that we say before the Shema, a blessing called “everlasting love,” will suffice in the breach. Simple enough. If you forget, the rabbis give you an umbrella policy. You’re covered.Not so fast! The medieval tosafists from Provence cite a caveat from the Jerusalem Talmud: This insurance policy works only if you study Torah immediately after prayers. If you go to work straightaway after prayers, you’re out of luck.But all of this was just a red herring, a gateway to the complexity that was about to come.What seemingly activates the need for a new blessing every morning is that night separates us from the last blessing the day before. Night, you say? Or is it sleep? What if you spent the whole night awake as we were doing just then in Chaim’s backyard? Come dawn, do we make a blessing on the Torah or not? What makes the difference, night or sleep? And if it is sleep, then how much sleep—a doze, a snooze, or a full blown night’s rest?The evening had begun with the Babylonian Talmud and as the hours wore on, we moved into the medieval heavyweights: the Rosh (Germany), the Rambam (Maimonides, from Spain and Morocco), the Ran of Catalonia Rashi (Troyes, France). At 3 a.m. we decided to break for watermelon and grapes and cheesecake.After the break I had to rally to fight back sleep. I could no longer concentrate even as the discussion had only now hit its hairsplitting high point: Does a short nap at night, with clothes on, mandate a new blessing on the Torah? How I longed for a bed. But it would be an embarrassment. We are the men who are supposed to hold up the Torah. What would our wives think of us if we wimped out? What’s more, the Talmud promises that he who fights sleep while learning Torah will be privy to the secrets of the universe.Yet even this promised blandishment was not enough. In the last hour as the Jewish moon migrated across the sky, I teetered between sleep and wakefulness and wandered into reverie. In the old synagogue of my youth, some of the young guys would pop out a board game like Risk when their attention to the Talmud waned. These games would continue till dawn. These guys, neighborhood toughs some of them, not exactly wired for the intricacies of Talmudic pilpul, they sat in the back, tieless with black Armani suits, their jackets hung up in the coatroom and sleeves rolled up as though they were waiters at a downtown club. Local lotharios some of them, as rumor had it, with their 1970s-style Afros—even they wanted to be awake. They recounted tales of glory and exploits, as they rolled the dice, a plate of cheesecake ever within reach.Now, sitting here with Chaim, my body began to wail in sleep deprivation. Even as I steadied myself, inwardly, I groused and began to “curse” the sin of the fathers. Why had they fallen asleep? Just now, Chaim nudged me out of my reverie. “It will soon be time for morning prayers.” The evening ended finally at first light, in the “company” of the leading luminaries of the late 20th century, Reb Moshe Feinstein and the Chazon Ish, Reb Shlomo Zalman Auerbach, respectively, who had the final words on the topic.We high-fived each other as we put the tallis on for prayers. Sleepily, we sang praises to God in the outdoors as the sun rose over Passaic and bade each other “gut yontiff” but the question for me lingered: Why had our forefathers fallen asleep? Was it as they say in Yiddish, an oifshtand, a full-fledged rebellion, or perhaps, from a psychoanalytic point of view, a necessary defense—a regression? Perhaps they knew what was ahead with a compassionate but complicated God who took them out of Egypt, yet “condemned” them forever as free men and women to the morally complex world. Like the bride on her wedding day with a case of cold feet—she may be terribly in love, yet she’s no fool. She wants the marriage, but she knows her groom and her marriage to him will be no day at the beach. (They say that when Moses stood at the Mount, he could see all of the future and the past—did he see the Holocaust?)In my work in psychotherapy, I have noticed that before people take on a great task, they go into a deep sleep sometimes literally, often figuratively. Bar mitzvah boys are famous for a fugue that befalls them the few months just prior to their big day. They dawdle, get lost, regress to childish levels as they struggle to both embrace and fight off adulthood with all their might. But not just young boys—bachelors, too, party before they get married, get themselves drunk, fall asleep. Many a Talmudic scholar, too, has broken out in a sweat on the eve of his ordination.One time when I was young, a Shavuot many decades ago, I went into a funk. I remember feeling as young men sometimes do, that the whole world is one big swindle. Sure, the Torah was important, but I wanted “more.” Why, I had fairly condemned myself to a backward world of Anatevka of customs and laws that would leave me languishing in a lifetime of unfulfillment. Sure, I thought: I will have functioned in a Torah life, but I will have died without having lived, I will have died without having lived my life.I needed to break away. So I decided to take a walk, a big walk—a straight line out of the barrio: Kew Gardens Hills, a place that seemed to me, at the time, saturated with sentimentality and self-indulgence, heavy even with its bric-a-brac of local color. God, the provinciality of my parents and the women of the neighborhood with their ankle-length skirts!Each step I took, I breathed with excitement as I walked along Queens Boulevard, away from the world of my father and over the 59th Street Bridge into Manhattan. All of a sudden I was at Lexington and 60th on a Wednesday afternoon near Bloomingdale’s, boutiques, women “dressed to kill” or simply to stoke men with their miniskirts or fashion flair (so it seemed to me). What intoxication! A freedom of the world of gentiles who knew nothing of the Torah and the gravity it imposed on men like me and my father.It was already late in the day. I took a cold drink and walked all the way back into Queens—about 27 miles in total—back to Anatevka.On the return walk I had a slightly different feeling. I walked past Astoria, Sunnyside, the Roosevelt Avenue el, Jackson Heights, Elmhurst. My separation from the people in these enclaves was actual enough—I walked in my holiday hat and suit—but there existed in me an unbreakable unity with all of New York, not just the Jewish parts and I ached with a helplessness to communicate a bond with these people in the glorious weather of a weekday in late May in New York. I wiped away big sweat and continued along Queens Boulevard toward Rego Park, Forest Hills, then took a left turn on Jewel Avenue. In the shadows of the shuls of my shtetl, hundreds of Queens immigrants played rugby and cricket in Flushing Meadows Park. They knew nothing of my holiday, but perhaps what happened at Sinai, gave a modicum of coherence to the entire world even as they didn’t know it the way I did. Back in the bedroom community of Kew Gardens Hills, people ambled out of their daytime Shavuot slumber and on to the evening service.Years later, after Chaim’s all-night study session, I came home and drank a large cup of holiday wine and at 9 a.m. I fell into a stone sleep. I had two dreams. In one my father appeared to me old, but his beard rich with red and white, his skin, the glow of fine olive oil. It was the first time since his death two years earlier that he appeared to me. He was silent but with his beautiful round bearded face, it was as though he were saying to his son, “Good.”In the second dream I had sinned with a woman, had done so with the strength of a much younger man and was about to be exposed for my sin. The dream and my sense of dread was so real that I was tearfully grateful when I woke to realize it was the mere product of wine and sleep.Yet, unlike most dreams these two didn’t evaporate in the course of the day. I was “stuck” with them, so I reviewed everything from the night before to try divine meaning. It had been a labor to stay up the whole night, yet these dreams might be the fruit of that labor. Chaim’s study session was built on the idea that the blessing called Ahava Rabba, or “everlasting love,” exempts you from saying the blessings on the Torah. Then it hit me. The dreams had been an attempt to answer an old riddle: Does love exempt you from or obligate you in life? Does love exempt you from labor and learning or does the love of God obligate you, no, mandate you—you must learn, you must endure the pain that learning requires.Some questions can only be resolved through sleep. Our forebears had witnessed the 10 plagues, walked across the Red Sea, been protected by heavenly clouds during the day in the desert and a pillar of fire at night to guide and warm them. The Almighty rained bread from the sky and drew water from stone. God loved them! Maybe love exempted them from the law or maybe not. They went to sleep. So, too, a bar mitzvah boy isn’t sure what to make of love. Often he regresses, but he comes to learn that without love there can be no law and without law there can be no love.My father represented to me the absolute cruelty and harshness of the learning of the law. While he loved me, his love of me obligated me to him and to his Torah. He absolutely did not spare the rod. He was wild-eyed with religious fervor (they used to call him “red”) and he “coerced” me in all kinds of ways. It could be said that I developed a false self to please him, but inexplicably in that false self there was a lot of love—and truth—and it went both ways, he for me as well.Improbably, my love for him and his Torah survived the torture intact. In this mangled, distorted, at times pure, at times deeply disfigured love, somehow I had made it through the night and I saw that it was good.