The JTrain Podcast – Chit Chat Wednesday

Episode: The Problem with People Pleasing ft Dr. Paula Freedman-Diamond

Host: Jared Freid
Guest: Dr. Paula Freedman-Diamond
Date: December 3, 2025

Episode Overview

This episode of Chit Chat Wednesday features psychologist Dr. Paula Freedman-Diamond, author of Toxic Striving. Jared and Dr. Paula delve into the often misunderstood subject of people-pleasing—what it really means, why we do it, and how it sabotages authentic connections and self-fulfillment. Through humor and relatable personal anecdotes, the duo explores relationship and dating challenges, the obstacles to asserting one’s needs, how technology and modern culture exacerbate these tendencies, and practical advice for cultivating healthier emotional boundaries.

Key Discussion Points & Insights

1. Origin Story and Book Background

• Dr. Paula shares how her husband reached out to get her on the podcast, highlighting her own struggle with self-promotion despite writing a book on living authentically.
  • [02:16] “I was really good at the writing of the book ... I suck at the, like, promotion part of it.” – Dr. Paula
• She recounts how releasing her book Toxic Striving coincided with a complicated pregnancy, which derailed her planned book tour.
  • [06:33] “I had to live in the hospital for, like, a month before my baby was born ... the hype moment kind of, like slipped through my fingers at the time.” – Dr. Paula

2. What is People Pleasing, Really?

• Both host and guest identify as people-pleasers but clarify the popular misconceptions:
  • [09:57] “It's not like a diagnosis. It's more like, you know, a self-described thing. ... It’s a ME problem. ... I don't like how I feel when someone's disappointed.” – Dr. Paula
• Jared admits he tries to avoid conflict and keep everyone happy, reflecting the self-serving aspect of people-pleasing.
  • [10:30] “I'm really trying to protect my own self. So I'm a huge piece of shit who doesn't want to feel badly.” – Jared

3. Consequences and Patterns

• People-pleasing can block intimacy and authenticity, particularly in dating and relationships.
  • [13:04] “People pleasing blocks intimacy ... I notice in my own relationships ... the more you want to, like, never upset anyone, you end up behaving in ways that are just like, not really true to you.” – Dr. Paula
• Different 'flavors' of people-pleasing in relationships: Dr. Paula people-pleases until resentful; her husband suppresses his preferences until he explodes.
  • [14:29] “He, like, holds back, holds back, holds back, and then, like, explodes out of nowhere one day when he, like, can't stand it anymore.” – Dr. Paula

4. Dating Dynamics: Single vs. Relationship

• Jared wonders if being single makes people-pleasing harder due to less certainty about the other’s reactions, realizing it's just “different flavors of the same mess.”
  • [14:15] “At least in a relationship, you know their level of anger ... as a single person ... everyone reacts to disappointment in different ways.” – Jared
• Dr. Paula observes that many people-pleasers end up dating selfish partners, but some, like her and her husband, attract fellow people-pleasers.
  • [17:08] “What I see more of is ... people-pleasers who date ... selfish people who ... expect to be catered to.” – Dr. Paula

5. Avoidance and Lack of Intimacy

• Avoiding honest conversations blocks opportunities for growth or actual closeness:
  • [18:16] “You're not giving the other person a chance to prove you wrong ... maybe they can handle being disappointed.” – Dr. Paula
• Jared recognizes that keeping relationships “light and fun” is a way to avoid messiness but also to his detriment:
  • [21:12] “Light and fun is, like, literally my nickname in a relationship ... but light fun doesn't get you close to someone.” – Jared & Dr. Paula

6. Modern Pressures: Technology, Social Media, and Impression Management

• The pressure to manage others' impressions is magnified by technology and “curated” digital lives.
  • [28:39] “So much of your energy gets sucked up into trying to control what you can't control ... Technology and AI and all of this ... is making it worse for us.” – Dr. Paula
• The fear of being recorded/judged affects even kids at events, and adults carry a sense of “being watched”:
  • [33:02] “My parents ... their reaction to a guy falling is so natural. And then mine is, like, I'm being watched by the police.” – Jared
  • [34:14] “They were afraid someone’s gonna video them dancing and spread it ... so they just don’t do it.” – Dr. Paula

7. Decision-Making in the Age of Labels

• The tendency to over-identify people by single labels in dating app culture, leading to snap judgments and self-censorship.
  • [36:34] “We get attached to labels and descriptions, and I think the Internet, I think like social media makes it worse ... there’s no flexibility.” – Dr. Paula
• Jared remarks on the pressure to “do a breakup press conference” and explain or justify choices to one’s social group.
  • [38:42] “You have to do a press conference ... knowing it’s not true, but feeling it is totally different.” – Jared

8. Acceptance & Commitment Therapy – A Path Forward

• Dr. Paula’s book leans on Acceptance and Commitment Therapy:
  • [27:21] “It’s about going back to your values ... You can’t control your thoughts, you can’t control your feelings. ... But you have control over your behavior.” – Dr. Paula
  • [28:38] “Can’t control how someone feels. Can control telling them how I feel and where I’m coming from.” – Jared

Notable Quotes & Memorable Moments

• [09:57] Dr. Paula: “No, it’s a me problem. It’s a—I don’t like how I feel when you’re upset with me … So it’s really kind of self-serving, you know, it’s like, how do I—I want to feel good inside.”
• [14:29] Dr. Paula: “My friend says it’s like a different flavor of the same sandwich.”
• [21:12] Jared: “Light and fun is, like, literally my nickname in a relationship ... but light fun doesn’t get you close to someone.”
• [33:02] Jared: “My parents live in this world where there’s no, like, camera shooting them.”
• [34:14] Dr. Paula: “One of the girls was like, ‘They’re afraid someone’s gonna video them dancing and like, spread it around ... so, like, they just don’t do it.’”
• [28:39] Dr. Paula: “I think the modern world ... is making it worse for us. I think it’s making us believe we can control everything.”
• [38:42] Jared: “You have to do a press conference ... knowing it’s not true, but feeling it is totally different.”

Important Timestamps

• 00:00 – 05:23: Introduction, guest bio, backstory of book and promotion woes
• 09:29 – 13:02: Defining people-pleasing; the real motivations behind it
• 14:15 – 16:34: Differences and similarities in people-pleasing for singles and couples; how it blocks intimacy
• 18:16 – 21:15: Avoidance, impression management, and why light/fun limits relationships
• 27:21 – 30:13: Acceptance & Commitment Therapy—focusing on controllable behaviors and values
• 32:09 – 34:50: Social media’s impact on authenticity and spontaneous living
• 36:34 – 40:17: The pitfalls of labeling and rigid identity in dating and relationships
• 44:00 – 49:37: “People Pleaser or Good Partner?”: A game exploring healthy boundaries versus self-abandonment

“People Pleaser or Just a Good Partner?” Game (44:02–51:43)

Jared and Dr. Paula play a lighthearted game testing real-world scenarios:

• Always deferring dinner choices: People-pleaser when it’s chronic avoidance.
• Giving up food without wanting a taste back: If it’s a test, it’s people-pleasing.
• Acts of service (e.g., driving to the airport): Not people-pleasing if genuinely done without resentment.
• Intimacy favors (e.g., sexual acts): Good partner if motivated by desire, people-pleasing if motivated by fear or guilt.
• Airplane upgrade controversy: Jared shares a story of accepting a first-class upgrade solo and later feeling regret about the optics and fairness, sparking a real talk about fairness, boundaries, and consideration in relationships.

Practical Takeaways

• Not all “nice” behaviors are people-pleasing; intention matters—are you acting out of genuine care, or out of fear/discomfort?
• Building tolerance to discomfort is like building a muscle: practice, allow imperfection, and focus on controllable actions.
• Authentic relationships grow through honest (sometimes uncomfortable) self-disclosure and boundary-setting.
• Modern life and technology both increase the urge to self-censor, but also make courage and authenticity more vital than ever.

For More:

• Toxic Striving by Dr. Paula Freedman-Diamond (Link in show notes and episode description)

End of Summary