Dating Smarter, Not Harder with Amy Chan

In this episode, John Kim sits down with relationship expert and author Amy Chan to talk about dating patterns, childhood wounds, grief, commitment, and what it really takes to build healthy love. Amy shares how the sudden loss of a close friend changed the way she thinks about relationships and why creating core memories with the people you love matters more than convenience. John opens up about how losing his home reshaped his idea of freedom, home, and what truly matters. Together, they explore how childhood neglect, validation-seeking, and old survival strategies continue to shape adult dating patterns. They also break down Amy’s framework for dating smarter, including how to spot where your dating life gets stuck, why apps should not be your only strategy, and how your energy affects connection. They talk about dopamine, fantasy, and why the first three months of dating can be misleading. Later, they unpack commitment, unrealistic expectations, relationship trade-offs, triggers, repair, and emotional safety. Amy explains her “Sh*t Bucket” concept and why healthy love is not about finding a perfect partner, but choosing someone whose imperfections you can actually live with. They close with a hopeful reminder: love is hard, but it is still worth building. In this episode: (00:00) The real reason your dating life keeps repeating(00:29) Grief changed how Amy thinks about love(02:09) John’s life after losing home and redefining freedom(03:15) Amy Chan on dating smarter and finding lasting love(05:03) The childhood wounds behind adult relationship patterns(10:29) The patterns sabotaging your love life(14:24) People can feel your dating energy(16:15) Why the first 3 months can fool you(20:02) Why love only grows when you go all in(23:30) Social media is warping our expectations of love(26:34) Every relationship comes with a “Sh*t Bucket”(28:57) Triggers, conflict, and healing inside relationships(33:24) What repair actually looks like in healthy love(37:08) What happens when only one partner wants to grow(43:14) Why love is hard and still worth it About Amy Chan: Amy Chan is the author of Unsingle: How to Date Smarter and Create Love that Lasts — a fun, science-backed dating guide that helps people interrupt the relationship patterns keeping love just out of reach and build healthier, lasting connections. Dubbed the “scientific Carrie Bradshaw” by The Observer, Amy has been a trusted voice in modern relationships for nearly two decades. In 2016, she founded Renew Breakup Bootcamp, the world’s first heartbreak retreat. She also leads Dating Bootcamp and is on faculty at Esalen and The Omega Institute. Her first book, Breakup Bootcamp: The Science of Rewiring Your Heart, was featured in The New York Times and optioned by a major streaming network. Her work has appeared in The Wall Street Journal, Good Morning America, The Today Show, The New Yorker, The Guardian, and USA Today. Books: Unsingle: How to Date Smarter and Create Love That Lasts (Pre-order) Breakup Bootcamp: The Science of Rewiring Your Heart Websites: (launching soon) Connect with Amy: Instagram Handle: LinkedIn URL: Tik Tok Handle: Twitter Handle: YouTube Handle: 🎙️ Host Links: 📘 Pre order my new book, Love Hard On Purpose. Toss the blueprints. Build something honest. 📘 Read John’s book in progress Sh*t Your Therapist Would Never Tell You on John’s SubStack ⁠HERE⁠ If you’re ready for deeper work, the Secure Self course is available HERE Order John's new book, Break Up. On Purpose,⁠⁠ ⁠⁠⁠⁠⁠⁠ HERE⁠⁠⁠⁠⁠⁠⁠⁠ Follow John on Instagram⁠⁠⁠⁠⁠⁠⁠⁠ HERE⁠⁠⁠⁠⁠⁠⁠⁠ Find out more about John⁠⁠⁠⁠⁠⁠⁠⁠ HERE⁠⁠⁠⁠⁠⁠⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Dating Smarter, Not Harder with Amy Chan is an episode from The Angry Therapist Podcast by John Kim.

This episode is 48:32 long.

This episode was published on Apr 20, 2026.

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