Skip to content
Jay Shetty PodcastJay 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

Jordana AbrahamguestJared FreidguestJay Shettyhost
Sep 2, 20251h 17mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Break dating burnout: ditch negativity, use apps wisely, date intentionally

  1. They argue that constant negativity about dating is emotionally validating but makes you a worse dater and less enjoyable to be with.
  2. Dating apps are framed as “fast food”: useful in moderation and intentionally, but damaging when they become your only dating strategy.
  3. Their proposed antidote to app fatigue is a practical “summer challenge” focused on deleting apps temporarily, getting off your phone, and rebuilding real-world social momentum.
  4. They unpack mismatched expectations between men and women—especially around attraction thresholds, commitment timelines, and the pressure of career/financial stability.
  5. They recommend simple communication moves (“make a plan and I’m in,” swapping “confused” for “turned off,” stating needs early) to reduce wasted time and increase clarity.

IDEAS WORTH REMEMBERING

5 ideas

Negativity feels good in the moment but sabotages your dating outcomes.

They describe dating cynicism as “biting a mosquito bite”: it provides temporary relief and community validation, yet it diminishes your energy, openness, and attractiveness on dates.

Treat dating apps like fast food: controlled, occasional, not a lifestyle.

Apps can help when you’re busy and can’t socialize, but mindless swiping creates fatigue, shallow volume, and more disappointment; they should be one tool among several.

Delete the apps temporarily to reset your brain and rebuild offline confidence.

Their summer challenge is a deliberate detox (June–August) designed to reduce phone dependency and reintroduce real-world interaction, so you return more energized—whether you re-download apps or not.

Replace app time with routines that increase “surface area for luck.”

They suggest concrete habits: eat out solo once a week with your phone away, join a new fitness class, and socialize with coupled friends monthly to widen weak-tie introductions without treating friends like matchmakers.

Men often filter first by attraction; women often filter by safety, stability, and long-term fit.

They argue this creates different experiences of “options,” with women more likely to apply multi-factor checklists (education, income, values) while men may decide quickly on physical attraction—fueling frustration on both sides.

WORDS WORTH SAVING

5 quotes

The negativity that's out there right now, while it's founded, like you can always be negative about dating, and you'll find a million people that will back you up and tell you how right you are for being negative about it, but it's the least helpful thing for your dating life.

— Jared Freid

Dating apps should be used, like, in the same way that fast food is.

— Jordana Abraham

We have to acknowledge who these w- apps were created for and by. Because they're not for you.

— Jared Freid

I think the best relationship advice I've ever seen is that if you look for what's missing from your partner, if you look for what they're not doing, what they could be doing more of, that's, like, gonna be the reality that you're living in.

— Jordana Abraham

Every time you say you're confused about something, exchange the word confused for turned off.

— Jared Freid

Negativity and dating mindsetDating apps as a tool (moderation vs dependence)Dating burnout and dopamine loopsThe “summer challenge” (delete apps, social routines)Attraction vs checklists (gendered patterns)Social media comparison and “high value” cultureChatGPT and scripted texting vs real-life connectionCommunication: needs, boundaries, and turned-off signals

High quality AI-generated summary created from speaker-labeled transcript.

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome