The New Rules of Dating for Ambitious Women with Amy Chan

Ambition 2.0

Girlboss

Entrepreneurship, Careers, Business

4.4 • 1.9K Ratings

🗓️ 20 January 2026

⏱️ 41 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 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 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 FOLLOW THE PODCAST 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 SIGN UP Subscribe to the Girlboss Daily newsletter: https://newsletter.girlboss.com/ For all other Girlboss links: https://linkin.bio/girlboss/ 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. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

Click on a timestamp to play from that location

0:00.0	We have a dating crisis right now. People, more and more people are single. People are not having
0:04.9	sex. People are not getting married. People are not having children. And people are lonelier than ever before.
0:10.6	So a lot of this advice, which causes us to mistrust people to be hyper vigilant of red flags is now, I think,
0:18.6	tip to the other side where we're walking around with walls.
0:22.8	And I just, I don't think that's conducive to the way human beings are wired, which is for
0:28.2	connection.
0:47.4	Welcome to Ambition 2.0, the new podcast from Girl Boss, where we explore what it really takes and costs to have it all in work, life, family, and love.
0:54.2	I'm your host, Amanda Gatz, two-time founder, five-time CMO, and author of the bestselling book, Toxic Grit, How to Have It All, and actually love what you have.
0:56.4	I am so excited about today's guest.
1:00.0	Let me just set the stage here.
1:02.3	She's a leading relationship expert, author of Breakup Bootcamp, The Science of Rewiring
1:07.6	Your Heart, a best-selling book.
1:09.9	She is the founder of the Renew Breakup Boot Camp
1:13.3	and Her New Book, Unsingle, How to Date Smarter and Create Love that Last is out this coming
1:19.1	April. Today's guest is Amy Chan. Amy, hello. Welcome to a Mission 2.0. How are you doing today?
1:26.6	I'm good. I'm great. It's an early morning. We're in Vancouver. I'm so excited. Your work has helped me so much as I've navigated, even post-divorce breakups. So I'm just so excited to dive in. I ask every guest this first question. What does ambition mean to you and how has it changed over the years?
1:48.3	I think when I was younger, ambition meant a lot of hustle and it meant having the title, it meant having the status, it meant having a lot of money and buying all the designer
2:02.6	things.
2:03.6	Right.
2:04.6	And now it's different.
2:06.6	I'm now in my 40s.
2:07.6	Ambition to me is really being clear on what your dreams are and not minimizing your dreams
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Girlboss, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Girlboss and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.