‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic

Old School with Shilo Brooks – The Free Press
Date: February 19, 2026
Host: Rafaela Seawart (interviewing Shilo Brooks, usually the show’s host)

Episode Overview

This episode of Old School departs from the usual format by featuring Shilo Brooks, typically the host, as the interviewee. Literary interviewer Rafaela Seawart guides the conversation, focusing on Vladimir Nabokov’s controversial novel Lolita: exploring its cultural influence, narrative complexity, and ongoing relevance in light of recent revelations in the Jeffrey Epstein case. The discussion delves into book’s troubling central relationship, the reasons for its persistent (and often misunderstood) presence in pop culture, and how grappling with such a work can illuminate both the darkest corners of human nature and the responsibilities of readers.

Key Discussion Points & Insights

1. Lolita’s Enduring Relevance and Real-Life Connections

• Current Context: The episode opens by noting that Lolita appears repeatedly in the newly released files related to Jeffrey Epstein (references in emails, photographs, and reportedly the only bedside book Epstein kept), making its cultural power and potential for misreading “deeply relevant in the current moment.” (01:10)
• Pop Culture: The novel’s illicit relationship has been glamorized or trivialized from Lana Del Rey and Katy Perry lyrics to Lena Dunham’s reading lists, a phenomenon likely to “shock the author.” (01:43)

2. Plot and Character: Humbert Humbert’s Perspective

• Narrative Framing: The story is a posthumous confession written in prison by Humbert Humbert, a self-admitted pedophile whose own troubled youth and parental trauma come to frame his later crimes. (02:28)
• Annabel Lee Parallels: The novel draws (or tempts the reader to draw) parallels between Humbert’s childhood love, Annabel, and his fixation on Lolita, yet doesn’t provide easy answers about roots of his psychosis: “He gives you a [choice]: [is it] something that happened to me in my childhood, or is it inherent…? And he doesn't tell us really which one he thinks.” (04:24)
• Unreliability: Nabokov’s use of a fictional forward narrator primes the reader to be wary of Humbert: “The perspective from which this book will be told is the perspective of an insane person.” (06:18)

3. Sympathy and Revulsion: The Reader’s Experience

• Uncomfortable Empathy: Nabokov’s skill lies in making the reader “sympathize with Humbert in a very bizarre way,” which fosters powerful discomfort and invites self-examination. (08:06)
  • Quote (08:06): “The genius of Nabokov is that sometimes he makes you despise—and you should despise—Humbert, but at other times you start to question yourself. And what that does is it makes you wonder about your own sanity.”
• Compelling Criminal: Humbert is written as charismatic—intelligent, literary, physically attractive—while also “objectively monstrous,” which is part of the novel’s disturbing allure. (10:00)

4. Lolita (Dolores Hayes): The Real Victim

• Only Through His Eyes: All we see of Dolores/Lolita comes filtered through Humbert’s predatory gaze. She’s “relatively normal” at first—interested in pop culture, mildly rebellious, suffering after the loss of her father—but over time, becomes a visibly traumatized child plied with gifts and subjected to ongoing abuse. (12:42)
• Agency and Seduction: Seawart and Brooks refute the popular interpretation of Lolita as a temptress, clarifying that every aspect of the relationship is marked by Humbert’s coercion and her victimization.
  • Quote (15:35): “At every moment, Humbert is the one in control. … There is no point at which Lolita comes to sight, as she might in popular culture, as a temptress. At every moment, she is a 12-year-old girl who is forced into a very bizarre and disgusting play with this man.” (15:35, Brooks)

5. Power, Escape, and Continued Abuse

• The Escape: Lolita flees after years of abuse, only to fall into the hands of another abuser, Claire Quilty, before eventually marrying a young man her own age. (19:04–22:48)
• Aftermath: Upon being reunited when Lolita is 17 and pregnant, Humbert “professes his love” for her even though she’s no longer a 'nymphet', exposing the twisted justification of his feelings and the demand on readers to consider what—if anything—redeems a love marked by predation.
  • Quote (25:05): “I think Nabokov is making us ask ourselves in our own soul: Does that legitimize all this? Does that make this okay, that this is true love?”

6. Art, Morality, and the Reader’s Role

• Narrative and Ethics: Nabokov’s stated lack of moral intent—“I do not give a damn for public morals in America or elsewhere”—raises questions about whether a book can be anti-pedophile while being narrated by a pedophile. (27:11)
  • Quote (27:11): “This is a book that requires you to have what one of my favorite philosophers called a tethered heart and a free mind.” (Brooks)
• Impact vs. Intent: While Nabokov’s literary ambition may not have been to change social norms, the book’s effect in the world has proven unpredictable: some (e.g., Epstein) read it as erotic; others see it as a damning indictment. (29:18–32:38)

7. Lolita and American Pop Culture

• Widespread Referencing: The “Lolita” figure persists in music, film, fashion, and more (36:33). There is, however, a consistent “erasure of Humbert Humbert” in popular retellings—Lolita becomes a symbol of sexuality, divorced from her abuse and from the system of power that made her a victim. (37:55)
• Film Adaptations: Kubrick’s 1962 film—called by the director “a very sad and tender love story”—omits or distorts much of the novel’s horror, presenting it more as dark comedy. (39:06)
• Cultural Fascination with Taboo: The book’s roots in taboo—particularly the desire to “get into the heads of those people” who break moral law—explain part of its allure and discomforting place in the canon. (40:48)
  • Quote (40:57): “We're obsessed with moral violation … we want in a way to get into the heads of those people and to live lives that we ourselves would forbid ourselves if we're sane, but are fascinated with nonetheless.”

8. Why Read Lolita?

• Difficult but Essential: Brooks argues Lolita is essential for a “capacious humanities education” because it investigates the boundaries of evil and longing, asking hard questions about human nature. (43:18)
  • Quote (43:18): “[Lolita] is a meditation on an ugly thing…if you want to acquaint yourselves with all that human nature is and is capable of … then Lolita has a rightful place in a capacious humanities education.”
• Literary Achievement: Beyond its content, the novel is written in stunning, distinctly non-native English prose—a feat that remains remarkable. (45:55)
  • Quote (45:55): “This was my experiment with the English language… just the words on the page and the way they're put together is astonishing.”
• Holding a Mirror to Society: The novel invites readers not just to examine Humbert’s psyche, but their own responses—both empathetic and horrified.
  • Quote (47:31): “We are asked to cross-examine ourselves by way of Nabokov asking us questions through Lolita.”

Notable Quotes & Memorable Moments

• On Humbert’s Disturbing Charisma:
  “Humbert comes to life as this charismatic, well spoken gentleman of a man who has this dark sin. … Who is charismatic at the same time that he's terrifying.” (10:00)
• Refuting the 'Temptress' Narrative:
  “There is no point at which Lolita comes to sight, as she might in popular culture, as a temptress… She is a 12 year old girl who is forced into a very bizarre and disgusting play with this man.” (15:35)
• On Nabokov’s Artistry Over Morality:
  “It is not my job to be the moral police. … I do not give a damn for public morals in America or elsewhere.” (28:55, paraphrased)
• On Lolita’s cultural myth:
  “Part of the myth around Lolita is dependent on the erasure of Humbert Humbert in pop culture. … We don't have Humbert Humbert as shorthand for, like, an abusive, predatory figure.” (37:55)
• On the Necessity of Confronting Evil in Literature:
  “If you want to acquaint yourselves with all that human nature is and is capable of… then Lolita has a rightful place in a capacious humanities education.” (43:18)

Timestamps for Key Segments

• Epstein’s Connection & Pop Culture References: 01:10–02:28
• Plot Summary & Structure: 02:28–05:02
• Is Humbert Reliable / Reader Vigilance: 05:49–07:13
• Empathy for Humbert & Reader Discomfort: 08:06–09:35
• Understanding Lolita (the Character): 12:42–14:57
• Refutation of Lolita as ‘Temptress’ Myth: 15:35–18:09
• Lolita’s Escape & Claire Quilty: 19:12–22:48
• The Return / “True Love?” Quandary: 24:27–25:05
• Narrative Ethics & Nabokov’s Stance: 26:32–29:18
• Publisher Misreadings & Impact vs. Intent: 29:18–32:38
• Pop Culture Appropriation & Film Adaptations: 35:33–39:06
• Sexual Taboo and Allure: 40:48–42:15
• Why the Book Matters / Reading the Uncomfortable: 43:18–45:36
• On Mastery and American Canon: 45:55–47:10
• Final Reflections on the Power of the Novel: 47:10–48:53

Tone and Language

Both Seawart and Brooks approach the topic with measured seriousness and intellectual rigor, neither shying away from the novel’s brutality nor shaming the impulse to read and discuss it. Brooks, well-versed in classical texts, positions Lolita within a broader tradition of literature’s willingness to probe the darkest recesses of the psyche, warning that readers must tether their hearts and “not be seduced by it, not romanticize it.” (43:18)

Final Takeaways

• Lolita endures because it refuses simple moral answers, instead drawing readers into the complexities of evil, love, and self-deception.
• The book is continually misinterpreted—by criminal abusers like Epstein, by pop stars, by filmmakers—partly because its narrative seduction is inseparable from its subject matter.
• Brooks argues the true value of reading Lolita lies in confronting, not glamorizing, what humans are capable of: “It holds up a mirror to, first of all, yourself … and the other aspect … is that people like Humbert exist in our society. … Better to shine light on it and try to understand it than to deny it and simply sweep it under the rug.” (47:31)

Episode closes with gratitude from both interviewer and interviewee for the rich, provocative conversation.