Upbringing and Gentlemanly Values

The Gstaad Guy sits down with Davide De Pierro, writer, storyteller, and viral voice behind The Letters I Never Sent, for a conversation that explores the messy, tender, and often hilarious reality of being human. Known for his clarity, honesty, and emotional precision, Davide reflects on the inspirations that shaped his writing, why “the how matters more than the what,” and the radical act of caring deeply in a world that rewards detachment.

The conversation dives into modern dating, expectations, accountability, and the quiet wisdom found in discovering how you truly feel. Davide unpacks the difference between being impressive and being loved, why perfection is a trap, and what role empathy plays in conflict resolution and navigating relationships. From role models to nostalgia, from self-awareness to the art of speaking simply, he offers a grounded and compassionate look at why so many of us struggle, and why none of us are alone in it. A thoughtful and emotionally resonant episode about relationships, identity, and the lifelong work of becoming a person.

Filmed at Casa Cipriani New York’s Premier River View Suite.

Chapters:

(00:00) Intro ✨

(04:59) The Inspiration ✨💡

(06:35) “Two Feet In One Shoe” 👣👠

(08:29) The How is More Important Than The What 🧭⚙️

(10:30) Caring Deeply ❤️🫂

(15:50) Writing Letters ✍🏻💌

(16:58) Captain America 🛡️🇺🇸

(17:49) “Find A Man Who Doesn’t Have Social Media” 🙅‍♂️📱

(22:45) Girl At A Bar 🍸👩

(25:54) Being Impressive vs. Being Loved 🌟❤️

(27:22) Expecting Perfection 🎯✨

(29:32) Be Monogamous In Your Dating Life ❤️🔒

(31:21) Role Models 🌟🧍‍♂️

(32:00) “Peasantry” 🧺😅

(36:38) Sharing Struggle With Someone 🤝🏻💭

(37:40) Wealthy People Don’t Love Each Other 💰💔

(40:16) “Peasant” 🧺😂

(41:57) Conflict Resolution & Problem Solving 🧩🤝🏻

(45:24) “It’s Easier For A Camel To Pass Through The Eye of a Needle…” 🐪🪡

(48:45) Accountability 🪞✔️

(50:04) Deficit of Self-Awareness 🤔❌

(53:04) Speaking Calmly & Simply 🧘‍♂️💬

(56:14) ”It’s Really Hard To Be A Person” 😔🌧️

(1:00:09) Trying To Change People 🔧👤

(1:01:58) Getting To Know People 👥💬

(1:06:30) Nightclub Analogy For Dating 🕺💘

(1:08:03) If It’s Not Sweet In The Beginning Then What’s The Point 🍯💞

(1:10:13) Accepting Someone’s Faults 🫂💛

(1:12:33) Taking Advice 👂🏻📘

(1:14:34) “The Letters I Never Sent” 💌🕊️

(1:16:11) Discovering How I Feel 🧠❤️

(1:19:42) Relationship Games 🎭🎯

(1:23:07) Toxic Tendencies ⚠️💔

(1:25:16) Women Always Know 👩‍🦰👀

(1:30:23) Remembering Someone Fondly 🌸💭

(1:32:04) Dealing With Your Ex 😬📱

(1:34:55) Reuniting With An Ex 🔄❤️

(1:36:05) Why We Want Partners ❤️🤝🏻

(1:38:49) Nostalgia 📼💞

(1:43:28) À La Poubelle vs. Fantastique 🗑️✨

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.