Break Stuff: The Story of Woodstock '99

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Introducing Selena Gomez & Benny Blanco EXCLUSIVE: Their Love Story Like You’ve Never Heard Before from On Purpose with Jay Shetty.

Follow the show: On Purpose with Jay Shetty

How did Selena and Benny first meet?

What makes their love story unique?

On today’s episode of On Purpose, Jay sits down with global superstar Selena Gomez and acclaimed music producer Benny Blanco where they share their love story like they never have before. They open up about their personal journey—one that didn’t start with an immediate spark.

Their story is full of humor, mixed signals, and that moment when it all clicked. Benny once thought Selena didn’t like him, while Selena, protecting her heart, kept her distance. But as their friendship grew, they built something real—a relationship rooted in trust, respect, open communication, and always supporting each other. Their story is a true testament that love unfolds when the timing is right.

Together, Jay, Selena, and Benny reflect on the power of embracing love, letting go of past fears, and choosing a partner who helps you grow. Their journey serves as a beautiful reminder that love often comes when you least expect it—but when it’s right, you’ll know.

In this interview, you'll learn:

How to Build a Strong Friendship Before Dating

How to Communicate Openly in a Relationship

How to Maintain Trust in a Long-Distance Relationship

How to Support Your Partner’s Emotional Needs

How to Balance a Busy Career with a Healthy Relationship

Selena and Benny’s story reminds us that true love isn’t defined by grand gestures or perfection—it’s about finding someone who sees you for who you are, supports you through life’s challenges, and makes even the simplest moments feel special.

With Love and Gratitude,

Jay Shetty

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!

What We Discuss:

00:00 Intro

01:10 Male Friendships Can Be Challenging

03:01 First Meeting & Deep Conversations

08:48 How It All Started

16:32 Opening Up to Love Again

18:57 It All Happens for a Reason

21:08 Finding Genuine Love

27:13 Be Kind to Yourself

33:37 Don’t Let Negativity Dictate Your Life

37:55 Cultivating Relationships with Trust

48:22 This is How Emotionally Mature Relationships Work      

57:08 The Proposal 

01:05:29 Wedding Planning

01:06:26 Recording an Album Together

01:13:17 Future Family Plans

01:18:03 Selena and Benny on Fun Questions

Episode Resources:

Selena Gomez | Website

Selena Gomez | Facebook

Selena Gomez | Twitter

Selena Gomez | Instagram

Selena Gomez | YouTube

Benny Blanco | TikTok

Benny Blanco | Instagram

Benny Blanco | YouTube

Benny Blanco | Twitter

Benny Blanco | Facebook

See omnystudio.com/listener for privacy information.

DISCLAIMER: Please note, this is an independent podcast episode not affiliated with, endorsed by, or produced in conjunction with the host podcast feed or any of its media entities. The views and opinions expressed in this episode are solely those of the creators and guests. For any concerns, please reach out to [email protected].

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Break Stuff: The Story of Woodstock '99By The Ringer | Luminary

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