Do you think your “type” limits you?

What’s one unrealistic dating expectation you’ve had?

Today, Jay welcomes back one of the most insightful voices in modern dating and relationships, Stephan Speaks. If you’ve been searching for clarity in love, struggling with self-worth in dating, or wondering why you keep attracting the wrong partners, this conversation is a must-listen.

Jay and Stephan kick off by breaking down one of the biggest struggles in today’s dating world—the negative perception of men and women. They explore how sensationalized online narratives and personal biases shape our beliefs about relationships, often distorting reality. Stephan explains how social media and exaggerated dating horror stories create unnecessary fear and distrust, making it harder for people to embrace love.

If you’ve ever felt like you’re stuck in a cycle of failed relationships, Stephan reveals that understanding yourself first is the key to finding the right partner. He emphasizes three critical factors: first, accepting the differences between men and women instead of resisting them; second, knowing yourself before entering a relationship, as many people struggle because they aren’t even clear on what they truly need; and third, prioritizing healing, because unresolved pain from past experiences will continue to affect every new connection.

In this interview, you'll learn:

How to Stop Letting Dating Myths Mislead You

How to Attract the Right Partner by Knowing Yourself

How to Heal Before Your Next Relationship

How to Communicate With a Closed-Off Partner

How to Break the Cycle of Failed Relationships

If you’ve felt frustrated, discouraged, or like love just isn’t in the cards for you, remember this: the right relationship isn’t something you chase, it’s something you attract by becoming the best version of yourself.

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Intro

01:28 The Difference Between Average Men and Women

11:30 Why Men Often Don't Date Ambitious Women

17:28 Understand Who Your Partner Really Is

23:55 Negative Perception of Men When Dating

28:52 Coveting the Desirables

32:27 How to Not Love Bomb Your Partner

40:32 If He Wanted to He Could

43:59 Emotional Maturity in Relationships

48:28 Always Be Open to Connection

53:34 Insecurities and Jealousy

01:01:15 How Do You Initiate Open Communication?

01:09:56 All Is Not Lost in Breakups

01:17:35 The Right Person at the Wrong Time

01:22:43 Every Dating Relationship is a Process

Episode Resources:

Stephan Speaks | Website

Stephan Speaks | TikTok

Stephan Speaks | Instagram

Stephan Speaks | Youtube

Stephan Speaks | LinkedIn

Stephan Speaks | Books

See omnystudio.com/listener for privacy information.

Highlights from O'Reilly's No Spin News - June 6, 2025