If You're Tired of Wasting Time on the Wrong People — THESE 9 Dating Questions Will Save You Years of Heartbreak!
On Purpose with Jay Shetty
iHeartPodcasts
4.8 • 28.5K Ratings
🗓️ 18 July 2025
⏱️ 36 minutes
🧾️ Download transcript
Summary
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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Transcript
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| 0:00.0 | This is an I-Heart podcast. |
| 0:04.4 | This week on Dear Chelsea with me, Chelsea Handler. |
| 0:07.7 | Marin Morris is here. |
| 0:09.3 | You came out of a marriage. |
| 0:11.2 | You came out of quote-unquote country music. |
| 0:13.7 | And you had a huge growth spurt from what I can tell. |
| 0:16.9 | I was expanding and growing at a really fast pace. |
| 0:22.5 | And yes, you could throw motherhood and the postpartum thing, learning about myself. |
| 0:27.0 | There were a lot of like identity crises going on. |
| 0:29.2 | But I realized like I can't look back and slow down for people. |
| 0:34.5 | Listen to Dear Chelsea on the Iheart radio app, Apple Podcasts, or wherever you get your podcasts. |
| 0:41.0 | If you're afraid to ask difficult questions in a relationship, it's because you might |
| 0:48.1 | already know the answer. |
| 0:51.3 | But that's not a good reason. |
| 0:53.2 | It's better to have the truth than a lie that feels better |
| 0:58.3 | than the truth. A lot of us will accept lies in a relationship, lies that we've made up in our |
| 1:04.3 | mind and our head because we don't want to face the truth. But the truth allows us to move |
| 1:09.9 | forward. Being in a healthy relationship isn't just about |
| 1:14.3 | chemistry. It's about clarity. The number one health and wellness podcast. Jay Shetty. Jay Shetty. |
| 1:21.9 | The one, the only, Jay Shetty. Hey, everyone, it's Jay Shetty and welcome back to On Purpose. |
| 1:30.8 | Today we're talking about something no dating app can teach you. |
| 1:34.9 | The conversations we're avoiding in modern dating. |
... |
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