Why You Are Stuck in an Endless Cycle of Dating! (And How to Fix it!)

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

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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:
   / @uuppodcast  
  / u.up.podcast  
https://x.com/uuppodcast
  / uuppodcast  

  / jayshetty  
  / jayshetty  
https://x.com/jayshetty
  / shettyjay  
   / @jayshettypodcast  
http://jayshetty.me