This episode is brought to you by Audible, Ancient + Brave, Strong Coffee Company and Fatty15.
Today we welcome relationship expert Amy Chan to break down the science of heartbreak, attachment patterns, and modern dating, revealing why breakups feel like addiction withdrawal and how high-performers often sabotage their healing by avoiding emotions instead of processing them. You'll learn how to stop ruminating on your ex, rebuild your identity after a breakup, and create new neural pathways through intentional action, as well as why strategies like "staying friends" or "winning the breakup" often backfire. Amy also shares her dating funnel framework, helping listeners understand how to move from casual dating to committed relationships while avoiding common pitfalls like confusing preferences with dealbreakers. This conversation is a powerful guide for anyone looking to move on faster, date smarter, and build healthier, more conscious relationships.
Follow Amy @missamychan
Follow Chase @chase_chewning
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00:00 – Why You Can't Skip the Pain of a Breakup
00:28 – Feeling vs Avoiding Emotions
00:58 – What Happens When You Suppress Pain
01:26 – Meet Amy Chan
01:51 – The Problem with Forcing Forgiveness
02:47 – The Science of Breakup Withdrawal
04:15 – Why Men Struggle More After Breakups
05:26 – Rebound Relationships Explained
06:30 – How Long It Really Takes to Heal
08:40 – Your Brain on Heartbreak (Addiction Comparison)
09:09 – Why No Contact Works
10:12 – The Reality of Avoiding Your Ex
11:11 – Why Doing Nothing Slows Healing
12:07 – How to Stop Ruminating
13:19 – Building New Neural Pathways
14:38 – Trying to "Win" the Breakup
15:57 – What to Do in the First 30 Days
17:19 – How Friends Should Support You
18:16 – Different Types of Breakups
19:53 – Should You Ever Get Back Together?
22:32 – Why Hooking Up with Your Ex Sets You Back
23:21 – The Danger of Staying Friends Too Soon
24:29 – Healing vs Avoidance
25:47 – Pedestal vs Villain Mindsets
27:32 – Living in Reality vs Fantasy
29:19 – The Dating Funnel Explained
31:03 – From Dating to Commitment
32:29 – Biggest Dating Mistakes Today
33:31 – Preferences vs Dealbreakers
34:28 – Dating Skills vs Relationship Skills
36:34 – How to Create Attraction on Dates
39:14 – Desperation & Dating Energy
41:25 – What Men Get Wrong on Dates
42:04 – Dating After Long-Term Relationships
44:23 – What Predicts Relationship Success
45:16 – Why Your "Type" Is Holding You Back
46:33 – The Dating Experiment That Works
49:31 – Dating Apps vs Real-Life Connections
51:27 – Optimizing Your Dating Profile
53:02 – Best Cities for Dating
54:54 – Aligning Strategy with Relationship Goals
56:56 – Are You Delusional in Dating?
58:30 – Money, Roles & Modern Relationships
01:00:28 – Navigating Family & Cultural Differences
01:02:30 – Final Lesson: Keep Your Heart Open
01:03:27 – What Relationships Are Really For
01:04:09 – How to Move Ever Forward in Love
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- Watch and subscribe on YouTube
- Get Amy's new book Unsingle