Written with candor, warmth, and emotional precision, GUESS WHAT? I LOVE YOU weaves together humor, heartbreak, spirituality, and healing. The memoir offers an intimate portrait of a relationship sparked by unexpected magic on a hookup app, deepened through a months-long phone courtship, and culminating in a life-changing first weekend walking hand-in-hand through New York City. Maimone captures not only Bragman’s larger-than-life public persona, but also the tenderness, vulnerability, and emotional generosity known only to those closest to him.
“Revisiting the hospital experience was the hardest part,” Maimone reflects. “I cried a lot while putting those moments on the page.” At times, the process was so excruciating that he admits he questioned why he put himself through writing the book at all.
A recurring thread throughout GUESS WHAT? I LOVE YOU is Maimone’s transformative “Year of Yes,” a period marked by openness, surrender, and the courage to release control over both life and career. Guided by Bragman’s mentorship and hard-earned wisdom, Maimone discovers balance, renewed creative clarity, and a healthier relationship with success; insights that resonate far beyond the entertainment industry.
Music remains central to Maimone’s storytelling. A lifelong album artist, he approaches the memoir with the same emotional intentionality that defines his songwriting, carefully shaping tone and narrative across each chapter. The accompanying album, also titled Guess What? I Love You, serves as a true companion piece, deepening the book’s emotional impact. Songs such as “Paranoid in Paradise,” “So Hard to Let Go,” and “Big Kiss” echo moments on the page, while the stories behind the music add rich new layers to the listening experience.
Throughout his journey, Maimone invites readers—especially those navigating grief—to embrace connection, remain open to unexpected possibilities, and allow themselves to experience the full spectrum of human emotion.
Visually, the book’s cover reflects the spirit of the story itself. Featuring illustrated cake pops (a symbol of joy discovered amid loss), the artwork honors a love story that didn’t unfold as planned, but was deeply meaningful, fully lived, and profoundly transformative.
