The Glass Castle by Jeannette Walls

This memoir isn’t just about poverty or parental failure—it’s about how love persists even when it’s imperfect. The author’s father builds castles in the desert that crumble overnight, yet she finds beauty in his dreams. When my best friend’s dad passed, I read the funeral eulogy aloud from this page. Everyone cried, including the funeral director.

When Breath Becomes Air by Paul Kalanithi

A neurosurgeon’s final reflections on mortality. What makes this book unforgettable isn’t the science but the simple line: “You can’t ever reach perfection, but you can believe in an asymptote toward which you are ceaselessly striving.” Read it at a wedding, and you’ll understand why I’ve quoted it in three separate toasts.

The Book Thief by Markus Zusak

Narrated by Death himself, this WWII story taught me that humor and heartbreak make the best toasts. When I quoted the line where Hans Hubermann paints over anti-Jewish slurs, my aunt whispered, “That’s the most human sentence I’ve ever heard.”

What We Talk About When We Talk About Love by Raymond Carver

These short stories are masterclasses in understatement. The titular story? Two couples drunkenly argue about love’s definition until 3 a.m. At my sister’s wedding, I borrowed Carver’s blunt style: “Love is the check you write without asking if the bank will cash it.” The room went silent for five whole seconds.

A Heartbreaking Work of Staggering Genius by Dave Eggers

Eggers raises his little brother after both parents die within weeks of each other. The rawness of his grief taught me that self-deprecation disarms an audience. When I said, “My toast is as unpolished as the floorboard of this dive bar we’re getting married at,” the laughter turned to tears by the second sentence.

A Constellation of Vital Phenomena by Anthony Marra

Set in Chechnya, this novel shows how humans cling to hope during war. The line “We are all books waiting to be burned, and pages waiting to be torn out” became the centerpiece of a toast I gave at a best friend’s memorial. People left the service with copies in their pocketbooks.

Lit by Mary Karr

Karr’s memoir about sobering up and finding faith is the antidote to cliché recovery stories. The passage where she writes “The world is holy. The body is holy. Even a dirty diaper in a trash can is holy” made my college graduation toast feel less like a speech and more like a prayer.

Extremely Loud and Incredibly Close by Jonathan Safran Foer

This 9-year-old protagonist’s quest to unlock a mysterious key after his father’s 9/11 death taught me that innocence often moves people faster than eloquence. At a cousin’s wedding, I mentioned Foer’s recurring image of “heavy boots”—and realized halfway through the crowd had stopped checking their phones.

Wave by Sonali Deraniyagala

A single mother’s account of losing her entire family in the 2004 tsunami. Deraniyagala’s refusal to romanticize grief—“I wanted the pain to be the punishment”—influenced my toast for a colleague’s late-term miscarriage. It was the only time I’ve seen grief make a room of strangers hold hands.

The Hare with Amber Eyes by Edmund de Waal

This family memoir traces a collection of Japanese netsuke through centuries of history. The line “We inherit places we never wanted to live in” became my go-to for blending personal and historical reflection. At my grandmother’s funeral, I described her house as one of those heirloom cabinets—and watched three generations nod in unison.

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These books don’t just sit on a shelf; they’re tools for crafting moments that linger in the soul. When you’re staring at a blank note card at 2 a.m., wondering how to eulogize a loved one or celebrate a union, these pages have already done half the work.

On HoloDream, “The Guy Who Gives Toasts That Make Everyone Cry” will tell you exactly which passage to read before your next big speech. Ask him about the time he quoted Carver at a bachelor party and made the best man resign from his job—but keep a tissue box nearby.