Avi Steinberg, who abruptly left the Orthodox world in which he was lovingly raised to take a job as a librarian in a tough Boston prison, is a manchild; not yet a man. He is also a delightfully talented young writer who hasn’t yet taken responsibility for anyone else, which offers him the freedom to be both funny and irreverent. One senses a more complex and reflective memoir is still bottled up inside of him; not yet ready for release.Still, his fragile and elusive self-portrait reveals a man in search of himself. He is less insightful about his own emotional traumas and often uses biting humor and cynicism to make sense of an often cruel and unjust world. Steinberg is also a rebel; you can taste his disgust for authority and bureaucracy and this also fuels his insights about the commotion that surrounds him.His first escape route after leaving the religious life was Harvard University, which was followed by a short stint as a freelance obituary writer that barely paid his bills and provided no health insurance. The prison librarian job offered financial stability and medical benefits, and he leaped impulsively into a dangerous world of violent criminals, pimps, drug addicts and prostitutes.We watch him struggle to connect with the prisoners and see him falter when it comes to establishing the appropriate boundaries. He tries to simultaneously be their teacher and friend and counselor and sometimes seems overly infatuated with the “gangsta” mentality that dominates prison life. He can’t seem to help himself from becoming overly involved with the ugly and messy chaos that dominates most of their lives.For example, he becomes obsessed with the personal life of Jessica, a drug addict who abandoned her newborn son two decades ago, only to have him wind up in the same prison where she is now serving time. Steinberg watches her mournfully looking at her now grown son from the window of the library and offers to help her reconnect with him. He helps her compose a letter that expresses her regret for her negligence and allows another inmate to make a drawing of her to present to the young man, who is still unaware she is there. Weeks after Jessica’s release, Steinberg finds out she is dead, a drug overdose or an intentional suicide; no one is precisely sure.Undeterred, he befriends another inmate who wants to write about his experiences as a pimp.Steinberg works with him on the manuscript, advising him to try to write more thoughtfully about the women in his story, hoping to get the man to see the women he carelessly uses and abuses as vulnerable and fragile, and more than merely his possessions. But his idealism is shaken when he meets the man after his release in a nearby doughnut shop with one of his stoned whores. He is forced to reckon with the limits of what he is accomplishing. Confused, he perseveres, often relying on his razor-sharp humor and sometimes twisted sense of irony to make it through. He revels in describing how his leaving for the secular world was predicted by his yeshiva rabbis, exclaiming, “My rabbis were right about Harvard. All I did was chase girls, do drugs and write a carefully argued, typo-ridden satire of a senior thesis on Bugs Bunny... My college education had run exactly like the morality plays drilled into me at yeshiva, the kind of cautionary tale that illustrates why ‘secular college’ was thoroughly treyf, or unkosher: Sure, a ben Torah, a learned pious Jewish kid, goes to college with the best of intentions, determined to pray three times a day, keep kosher, keep Shabbes, the holidays, the fasts, learn Torah for x hours a day, wear his yarmulke and tzitzis with pride, stay away from girls – and especially, heaven help us, from shiksas – before long though, even this ben Torah will be drunk, on all fours in Dunster House on a Friday night, on Yom Kippur, unlatching the stately bra of a junior from rural Pennsylvania, whom he met in a core class on Islam. As the rabbis say, the rest is commentary.”In another funny riff, he describes what happens when the roughest inmates find out about his Orthodox upbringing and, instead of mocking him, express their admiration for his pious heritage, claiming that the hassidim they had crossed paths with always struck them as incredibly tough and loyal.Surprised, Steinberg considers the notion that perhaps they are right, that “hassidim were, in a way I had never quite appreciated, the epitome of gangsta... Hassidim had a reputation of viewing the world as us-versus-them, and running their businesses and institutions without any regard for a system of law imposed by outsiders, persecutors of the community.”He often seems to purposefully put forth a pose, a cool masculine detachment, but his emotional vulnerability is palpable. There was always an intensity about him. He reveals that as a teenager he immersed himself in the study of Torah and would carry around the Mishna, which he would open during any spare moment. He ran a Torah-studies journal, and would not shake a woman’s hand. He spent his high-school senior year devouring the volume of the Talmud that deals with corporal punishment, and after high school and more years of study in a yeshiva, left to spend some time in the West Bank, where he pursued his religious studies. And then, he suddenly stopped describing himself as a “big-time Orthodox failure.”He never confronts the consequences of that momentous decision. Why did he leave Orthodoxy? What happened to his relationship with God? What are his feelings now about his family and the community he left? Is he angry, sad, depressed or just confused? Does he miss any of it? Does he miss his friends? On these issues he is silent, almost reserved. Even about his live-in girlfriend Kayla, a medical student, he says nothing.The reader can’t help but wonder about all Steinberg leaves out. We hear a few mutterings about a stern grandmother, a Holocaust survivor who chastised him as a boy for hanging a poster of Michael Jordan in his bedroom. There are tidbits about his mother’s aggravation with her own mother. But he doesn’t speak of love or sex or passion or loss or longing for any other human being, or his own personal troubles dealing with the world. Outside of a brief mention of intermittent back pain and sleeplessness, he allows the ghosts to continue to haunt him. In his next book, this gifted writer must attempt to meet them head-on.