| Image | Voter | Winner | Loser | Reason |
|---|
 | Greg Brockman | The Journals of Anaïs Nin | The Freedom Writers Diary | Anaïs Nin's introspective and avant-garde style offers a deep dive into the human psyche, making it a more profound read for those who dig the complexity of human experiences. |
 | Larry Page | The Journals of Anaïs Nin | Dear Dumb Diary | Anaïs Nin's journals dive deep into the human psyche and offer profound insights, which is right up my alley as a lifelong learner and seeker of innovation. |
 | Nerds | The Journals of Anaïs Nin | Dear Dumb Diary | The Journals of Anaïs Nin are like a deep dive into the soul, while Dear Dumb Diary is more of a fun splash in a kiddie pool. |
 | Socrates | The Journals of Anaïs Nin | Bridget Jones's Diary | Given my philosophical bent, The Journals of Anaïs Nin, with its introspective and existential depth, resonates more profoundly with me than the modern, light-hearted musings of Bridget Jones's Diary. |
 | Jensen Huang | The Absolutely True Diary | The Journals of Anaïs Nin | The Absolutely True Diary is a compelling, modern take on identity and resilience that resonates with today's youth in a way that only a poignant coming-of-age story can. |
 | Tim Berners-Lee | The Journals of Anaïs Nin | Dear Dumb Diary | The Journals of Anaïs Nin offer a profound exploration of human psyche and literary depth, appealing to those who dig introspective and complex narratives. |
 | Carl Sagan | The Journals of Anaïs Nin | The Freedom Writers Diary | The Journals of Anaïs Nin offer a cosmic introspection into the human psyche, interweaving personal insight with the broader tapestry of human experience, much like contemplating the universe itself. |
 | Andy Weir | The Journals of Anaïs Nin | Dear Dumb Diary | Anaïs Nin's journals offer a rich, introspective dive into the human condition, like a literary deep space exploration, whereas Dear Dumb Diary is more like a fun jaunt to Mars with humor and sass. |
 | Charles Babbage | The Diary of Anne Frank | The Journals of Anaïs Nin | As a chronicle of youthful resilience and courage amidst the grim realities of war, The Diary of Anne Frank is a poignant testament to the human spirit that resonates across time. |
| Socrates | The Journals of Anaïs Nin | Go Ask Alice | Anaïs Nin's journals offer a raw, artistic insight into a complex mind, whereas Go Ask Alice feels more like a cautionary tale. |
 | Steve Wozniak | The Journals of Anaïs Nin | Go Ask Alice | The Journals of Anaïs Nin offer a richer, more authentic glimpse into the complexities of life and creativity, aligning with my appreciation for depth and innovation. |
 | Professor Farnsworth | The Journals of Anaïs Nin | The Absolutely True Diary | Great Scott! Anaïs Nin takes the cake with her intimate exploration of human emotions and relationships, which aligns with my appreciation for complex, mature narratives. |
| Professor Farnsworth | The Journals of Anaïs Nin | Go Ask Alice | The Journals of Anaïs Nin offers an authentic and introspective exploration of life and creativity, whereas Go Ask Alice is a controversial and largely fictionalized account. |
 | Albert Einstein | The Journals of Anaïs Nin | Bridget Jones's Diary | Anaïs Nin's introspective and profound exploration of the human psyche resonates with my love for deep intellectual inquiry. |
 | Pythagoras | The Journals of Anaïs Nin | The Absolutely True Diary | Anaïs Nin's journals, man, they're like a deep dive into the human psyche, far out and timeless compared to the contemporary vibe of The Absolutely True Diary. |
 | Pliny the Elder | The Journals of Anaïs Nin | Go Ask Alice | Anaïs Nin's journals offer a profound and nuanced exploration of the human experience, making them more intellectually enriching than the controversial Go Ask Alice. |
 | Marie Curie | The Journals of Anaïs Nin | The Freedom Writers Diary | As a scientist, I cherish introspection and discovery, and Anaïs Nin's journals offer a profound dive into the human psyche, much like a scientific journey. |
 | Alex Trebek | The Journals of Anaïs Nin | Diary of a Wimpy Kid | The Journals of Anaïs Nin offers a profound exploration of the human psyche and artistic expression, appealing to those who appreciate literary depth and historical context. |
| Larry Page | The Journals of Anaïs Nin | Go Ask Alice | Anaïs Nin's introspective and groundbreaking diaries offer a deeper and more authentic exploration of the human psyche, unlike the dramatized narrative in Go Ask Alice. |
| Professor Farnsworth | The Diary of Anne Frank | The Journals of Anaïs Nin | Good news, everyone! Anne Frank's diary gives a raw and poignant glimpse into the human spirit during unimaginable adversity, making it a more universally impactful read. |