Lori Gottlieb: 7 Answers to Dating Questions You’re Afraid to Ask & How to Break Free from Relationship Timelines

Have you ever felt stuck in a negative relationship cycle?

Have you ever struggled with setting boundaries in your relationships?

Today, Jay welcomes back a community favorite, the renowned psychotherapist, bestselling author, and podcast host Lori Gottlieb, for an insightful chat about love, relationships, and emotional growth. Lori, best known for her book Maybe You Should Talk to Someone and as co-host of the popular Dear Therapists podcast, brings her deep wisdom and practical advice that really hits home with listeners.

Lori shares how people often step into love with unrealistic expectations, thanks to social media and pop culture. She reminds us that while the spark of initial chemistry is thrilling, true, long-lasting love thrives on a deeper connection and genuine understanding. One of the highlights is Lori’s take on “idiot compassion” versus “wise compassion.” She breaks down how real compassion means looking at ourselves honestly, recognizing our patterns, and owning our part in the relationship. This is essential for anyone feeling trapped in negative cycles.

As the conversation unfolds, Jay and Lori dive into family dynamics, especially around in-laws and blending families. Lori offers practical tips on how to support your relationship while still showing respect for parents, pointing out that these challenges are usually a couple's issues, not just external ones.

In this interview, you'll learn:

How to Let Go of Unrealistic Expectations

How to Practice Wise Compassion

How to Break Negative Patterns

How to Handle Pressure to Rush Relationships

How to Prioritize Clear Communication

How to Avoid Pop Culture Relationship Pitfalls

How to Cultivate Emotional Resilience

Remember, true connection flourishes when we commit to growth, communicate openly, and remain empathetic to both ourselves and others. Every step taken toward understanding and compassion brings you closer to creating a life filled with genuine, lasting connections.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

02:29 What is Everyone Doing at My Age?

05:08 Why Doing Self Work Matters

08:40 Why You Need to Slow Down to Save Time

13:03 How Your Attachment Style Affects Your Relationship

17:03 First Date Impressions Aren’t Always Accurate

21:26 How Do You Define Real Human Connection?

24:33 Do You Fully Understand Your Partner?

28:24 Learn to Communicate Your Desires

31:26 This is What Happens When You Don’t Communicate

35:24 Why We’re Unreliable Narrators of Our Story

37:52 Be Consistent with Your Boundaries

42:36 We All Want to Be Liked

45:46 You’re Not Ready to Marry Yet

49:51 Practice Being Your True Self All the Time

52:36 The Blind Spots of Dating

57:08 The Truth About Future Tripping

01:00:10 How Do You Feel About the Other Person?

01:01:33 The 7-Year Mark of Marriages

01:03:50 Can Having Children Save a Marriage?

01:07:35 In-Law Issues is a Couple Issue

01:12:01 The Concept of Feeling Felt

01:16:50 How Long Can You Tolerate Disrespect from Your Partner? 

Episode Resources:

Lori Gottlieb | YouTube

Lori Gottlieb | Instagram

Lori Gottlieb | Website

Dear Therapists Podcast

Maybe You Should Talk to Someone

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