Are you making time for the kind of love you want?

Do you feel like you’re ready to stop repeating old patterns?

Today, Jay welcomes Jared Freid and Jordana Abraham, hosts of the hit dating podcast U Up?, for a candid, lighthearted look at modern love. Together with Jay, they unpack why dating feels tougher than ever, from app burnout to myths about what it means to be “dateable,” and how negativity online makes the process feel heavier than it is. Instead of rigid rules, they offer a mindset shift: lead with curiosity, keep your attitude light, and build on a life you already love, not one you expect someone else to complete.

The conversation dives deeper into the nuances of attraction, commitment, and the subtle ways we self-sabotage. Jared shares how men often end relationships early, not out of rejection, but out of fear of responsibility and the lure of endless options. Jordana, emphasizes how mindset is 70% of dating, and how showing up fulfilled and confident makes you more magnetic than trying to “fit” someone else’s ideal. Together they discuss the unrealistic pressures of the social media highlight reel and how that can warp expectations and undermine authentic connections.

In this interview, you'll learn:

How to Date Without the Negativity

How to Be the Best Version of Yourself on a Date

How to Turn Confusion Into Clear Boundaries

How to Avoid Self-Sabotaging in Relationships

How to Stay Grounded Amid Social Media Comparisons

How to Build Confidence by Building a Full Life Outside Dating

The most powerful shift you can make is choosing to approach love with openness, positivity, and confidence in your own worth. When you lead with curiosity instead of fear, with joy instead of judgment, you not only create better connections, but you also become more grounded in who you are.

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.

What We Discuss:

00:00 Intro

03:36 Negativity Doesn't Make You a Better Dater

07:55 Dating Burnout

14:27 You Shouldn’t Just Rely on Dating Apps!

18:06 The Checklist for Dating

22:34 Staying Single in Your 40s

23:59 The #1 Reason Why Men Go on Dates

27:05 Attitude Is Everything

29:45 What is The Best Relationship Advice?

21:18 How to Be the Best Version of Yourself

35:19 Don't Fall for Social Media Relationships

36:01 Using ChatpGPT to Create Messages

39:00 Why Small Talks Matter

42:06 Do Men Actually Have More Dating Options?

44:51 The One That Got Away

47:42 Are Men and Women Different in Long-Term Relationships?

50:15 Difficult Conversations Every Couple Needs to Have

52:20 The Fear Most Men Have When Dating

57:28 What Makes a Successful Marriage?

01:03:27 Marriage is Choosing Your Partner Every Day

01:05:30 Jared and Jordana on Final Five

Episode Resources:

U Up? | YouTube

U Up? | Instagram

U Up? | X

U Up? | TikTok

See omnystudio.com/listener for privacy information.

Episode 22 - Gregg Mauro, Program Director & Senior Fellow at The Conference Board