EPISODE · Jun 16, 2026 · 53 MIN
#326 How People Pleasing Makes Breakups Harder with Dr. Paula Freedman Diamond
from Heal Your Heartbreak
In today’s expert episode, I’m interviewing Dr. Paula Freedman Diamond, a licensed clinical psychologist, speaker, and author of the new book “Toxic Striving: Escaping the Stress and Burnout of Hustle and Diet Culture.” We talk about the many faces of people pleasing and perfectionism, how these patterns show up in dating and relationships, and how suppressing your own needs can eventually lead to relationship breakdowns or unhealthy dynamics. Dr. Paula shares both her personal experiences and practical therapeutic insights on building real intimacy, navigating conflict, and coping with heartbreak when you’ve always tried to be the “perfect” partner. We also discuss controlling the narrative after a breakup, learning to sit with uncomfortable feelings instead of rushing to fix them, and how embracing your needs and authenticity is key to healing from heartbreak. If you struggle with people pleasing, overthinking, or feeling like you have to do it all, you’re not alone—and you don’t have to stay stuck in these cycles.To find out which Break Up Bestie Course is right for you, click the link to take the quiz and get matched with the best solution for you: https://tally.so/r/Y5Z6LNTo get my course bundle Heal Your Break Up, go to https://www.breakupbestie.com/heal-your-break-up-course and use the code PODCAST for $25 off!To join Healing Hearts Club for FREE: https://www.facebook.com/groups/1021288124899873Patio season is here and these deals won’t last! head to Wayfair.com right now to get your outdoor space ready for way less. That’s WAYFAIR.COMUpgrade your sleep with Boll & Branch. Get 15% off your first order plus free shipping at BollAndBranch.com/heartbreak with code heartbreak. You don’t have to say yes to everything this summer. Find support in therapy. Sign up and get 10% off at BetterHelp.com/heartbreakSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
What this episode covers
In this episode of Heal Your Heartbreak, Kendra interviews psychologist and author Dr. Paula Freedman Diamond about overcoming perfectionism, people pleasing, and toxic striving in relationships and breakups, offering practical advice for healing and developing authenticity.
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#326 How People Pleasing Makes Breakups Harder with Dr. Paula Freedman Diamond
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