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 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: https://www.youtube.com/@uuppodcast https://www.instagram.com/u.up.podcast/ https://x.com/uuppodcast https://www.tiktok.com/@uuppodcast https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me

Jordana AbrahamguestJared FreidguestJay Shettyhost

Sep 3, 20251h 17mWatch on YouTube ↗

EPISODE INFO

Released: September 3, 2025
Duration: 1h 17m
Channel: Jay Shetty Podcast
Watch on YouTube: ▶ Open ↗

EPISODE DESCRIPTION

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: https://www.youtube.com/@uuppodcast https://www.instagram.com/u.up.podcast/ https://x.com/uuppodcast https://www.tiktok.com/@uuppodcast https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me

SPEAKERS

Jordana Abraham
guest
Co-founder of Betches and dating podcast co-host known for relationship and modern dating commentary.
Jared Freid
guest
Stand-up comedian, writer, and dating podcast co-host who discusses dating from a male perspective.
Jay Shetty
host
Host of the Jay Shetty Podcast (On Purpose), author, and former monk who interviews guests on wellbeing and relationships.

EPISODE SUMMARY

In this episode of Jay Shetty Podcast, featuring Jordana Abraham and Jared Freid, Why You Are Stuck in an Endless Cycle of Dating! (And How to Fix it!) explores break dating burnout: ditch negativity, use apps wisely, date intentionally They argue that constant negativity about dating is emotionally validating but makes you a worse dater and less enjoyable to be with.

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