If You're Tired of Wasting Time on the Wrong People — THESE 9 Dating Questions Will Save You Years of Heartbreak!
Today, Jay reframes how relationships are built—not through surface-level attraction or blind chemistry, but through clarity, communication, and intentionality. He presents nine transformative questions that often go unasked in modern dating, not because they’re unimportant, but because they’re uncomfortable. Jay explains that avoiding these conversations leads to assumptions, unmet expectations, and unnecessary heartache. He underscores that a healthy relationship isn't defined by constant harmony, but by the courage to ask, listen, and grow together.
Blending personal stories, practical wisdom, and psychological insight, Jay highlights how asking the right questions early can reveal compatibility, values, and emotional readiness. He breaks down how these conversations create a shared language, prevent miscommunication, and ultimately strengthen the foundation of any relationship. Rather than using questions as ultimatums or pressure points, he encourages approaching them with curiosity and empathy.
In this episode, you'll learn:
How to Ask What a Healthy Relationship Means to Your Partner
How to Talk About Fears Around Commitment Without Pressure
How to Discuss Conflict Styles Before an Argument Happens
How to Know If Someone Is Truly Ready for a Relationship
How to Align on Boundaries and Independence in Love
Love doesn’t have to be a guessing game. The more willing we are to ask real questions and embrace honest conversations, the more aligned, peaceful, and fulfilling our relationships can become.
With Love and Gratitude,
Jay Shetty
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What We Discuss:
00:00 Intro
02:03 The Conversations We Avoid in Modern Dating
03:36 #1: What Defines a Healthy Relationship?
08:17 #2: What are You Afraid of When It Comes to Commitment?
12:30 #3: How Do You Handle Conflicts?
19:44 #4: What are Your Long-Term Intentions?
22:02 #5: What Does Emotional Availability Mean to You?
25:10 #6: Do You Prefer to Recharge Alone?
27:49 #7: What Does Being Ready Mean to You?
31:30 #8: What Does Independence Look Like to You?
32:52 #9: What Are You Still Healing From?
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On Purpose with Jay Shetty
I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace.
I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!
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