Dating in 2026 can feel… bleak. Everyone is analyzing “red flags,” burned out on dating apps, and building emotional walls to stay safe out there. Sound relatable?
In this episode of Ambition 2.0, Amanda Goetz sits down with relationship expert Amy Chan—founder of Renew Breakup Bootcamp, bestselling author of Breakup Bootcamp, and author of the upcoming book Unsingle: How to Date Smarter and Create Love That Lasts—to talk about what’s actually going wrong in modern dating (especially for ambitious women) and how to date smarter.
Dating in 2026 can feel… bleak. Everyone is analyzing “red flags,” burned out on dating apps, and building emotional walls to stay safe out there. Sound relatable?
In this episode of Ambition 2.0, Amanda Goetz sits down with relationship expert Amy Chan—founder of Renew Breakup Bootcamp, bestselling author of Breakup Bootcamp, and author of the upcoming book Unsingle: How to Date Smarter and Create Love That Lasts—to talk about what’s actually going wrong in modern dating (especially for ambitious women) and how to date smarter.
Amy breaks down why high-achieving women can accidentally bring “CEO energy” into their love lives—turning dating into a project, over-functioning, and doing 90% of the work. You’ll learn how to stop over-giving, create space so someone can actually show you who they are, and why it’s not your job to coach someone out of their insecurity.
Plus, Amy shares her “dating funnel” framework (lead generation → evaluation → commitment) and the underrated stage most people skip: the evaluation phase (a.k.a.: dates 3–20, where character is revealed).
If you’re dating right now—or you want a smarter path to partnership—this episode is for you.
You’ll learn:
Why modern dating feels broken—and how hyper-fixating on red flags is actually blocking connection
How “CEO energy” can sabotage dating and what to do instead
Why it’s not your job to fix or coach a partner out of insecurity
What emotional wealth really means (and why it matters more than money)
Amy’s “dating funnel” framework and why dates 3–20 are crucial
How “ick culture” keeps people single
How to reopen your heart if dating has made you guarded, burned out, or distrustful
00:00 Intro
03:22 Women’s standards are rising—and “survival coupling” is over
05:04 What is the “CEO energy” problem?
07:26 How to leave space and let them show who they are
10:12 Emotional wealth > financial flex: what men can do differently now
14:50 Amy’s dating funnel framework
21:08 The internet’s worst dating advice
GUEST LINKS
Instagram: www.instagram.com/missamychan
TikTok: https://www.tiktok.com/@missamychan
Read Breakup Bootcamp: https://bookshop.org/a/116169/9780062914743
Pre-order Unsingle: https://bookshop.org/a/116169/9781419779848
www.renewbreakupbootcamp.com
www.missamychan.com
www.hearthackersclub.com
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IG: https://www.instagram.com/girlboss/ | TikTok: https://www.tiktok.com/@girlboss
Amanda Goetz: https://www.instagram.com/theamandagoetz/
https://girlboss.com/pages/ambition-2-0-podcast
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ABOUT AMBITION 2.0Powered by Girlboss, Ambition 2.0 is a podcast where we’ll be exploring what it really means to “have it all” in work, family, identity, and self… and if it’s actually worth it. Each week, you'll hear from hardworking women who’ve walked the tightrope of ambition. They'll share their costly mistakes, lessons learned, and practical tips for how to have it all and actually love what you have.
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