Jay Shetty Podcast

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

JAJordana AbrahamguestJFJared FreidguestJSJay Shettyhost

Sep 3, 2025·1h 17m·Watch on YouTube ↗

📖 CHAPTERS

1. 1

   Why negativity keeps you stuck (and what to replace it with)

   Jared argues that modern dating culture rewards cynicism—online, negativity gets validated and goes viral—but it actively harms your chances of connecting. The trio reframes being single as a hopeful, opportunity-filled season rather than a failure state.

2. 2

   Dating app fatigue: treat apps like fast food, not a food group

   Jordana compares dating apps to fast food: useful in moderation, harmful as a primary diet. They emphasize intentional, bounded app use and warn against mindless swiping that creates burnout and resentment.

3. 3

   The Summer Challenge: delete apps and rebuild real-world momentum

   Jared lays out a practical three-month reset: delete the apps and replace the dopamine loop with structured offline behaviors. The goal isn’t instantly finding a partner—it’s becoming energized, social, and present again.

4. 4

   “Be Coca-Cola”: leverage loose ties and stop networking for outcomes

   They explain how hanging with partnered friends isn’t about extracting introductions; it’s about being memorable and genuinely connected. If you show up as your best self, friends’ partners naturally think of you when opportunities arise.

5. 5

   Checklists, attraction, and what men/women optimize for

   Jay raises the perception gap: many impressive single women struggle to find comparable single men. Jordana and Jared discuss differing filters—women often evaluate safety/stability/life trajectory while men commonly start with attraction—creating mismatched pools and expectations.

6. 6

   Attitude is the multiplier: confidence beats “trying harder”

   They argue that going on more dates while carrying burnout, resentment, or scarcity doesn’t work—people feel it immediately. A happy, engaged presence can increase attraction more than looks, while a sour mindset can sink even a strong match.

7. 7

   Social media relationship myths and the “high value” trap

   They critique internet-driven status scripts: model-level beauty standards for women and extreme wealth/provider standards for men. Constant comparison to highlight reels (e.g., lavish gifts/trips) distorts what you actually want and erodes satisfaction.

8. 8

   ChatGPT and texting: a tool, not a substitute for real connection

   Jay asks about AI-written messages; they agree it can improve clarity (especially for breakup texts) but shouldn’t replace authentic intent. They note people have always used “proto-AI” (friends, Googling) to craft texts—what matters is getting in-person quickly enough to verify chemistry.

9. 9

   From chat to date: avoid extremes and optimize for safe + excited

   They reject rigid rules like “skip small talk” or endless pen-pal messaging. Jared’s core heuristic is that you should meet when you feel both safe and excited, and that timeline can vary by person and context.

10. 10

    Commitment anxiety, choice paralysis, and ‘the one that got away’

    Jordana and Jared explore why men may end things before the “next step,” tying commitment to identity, responsibility, and life trajectory. Jared shares that fear of making choices affect someone else—and of stepping into adulthood roles—can keep men in the comfort of “potential.”

11. 11

    What marriage is really like: choosing your partner every day

    Jay asks Jordana to reflect on the realities of marriage and partnership. She emphasizes that commitment is less scary in practice than in imagination, and that marriage is an ongoing daily choice grounded in gratitude, growth, and shared resilience.

12. 12

    Final Five lightning round: practical scripts and mindset reframes

    They close with rapid-fire scenarios and concrete language to reduce ambiguity and reclaim agency. Key takeaways include asking the other person to make a plan, interrogating jealousy and ‘impressiveness,’ and replacing vague confusion with specific “turned off” communication.