On Purpose with Jay Shetty - 4 Ways to Make Dating Feel Exciting Again

Episode Date: October 14, 2026

Jay explores why first dates have started to feel more like performance reviews than opportunities for connection. He shares four ways to make dating feel fun and exciting again, from leading with curiosity and embracing new experiences to finding something valuable in every date and bringing a little romance back into your love life. With Love and Gratitude, Jay Shetty Instagram Teen Accounts: Built-in protections for teens. Learn More. At https://chase.com/sapphirereserve JAY'S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here: https://news.jayshetty.me/subscribe Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast What I Discuss: 00:00 Introduction 00:25 Dating Burnout And Fatigue 01:50 Wanting Connection But Dreading Dating 02:35 First Dates As Performance Reviews 04:19 Curiosity Over Optimization 06:00 Evaluating People Vs. Experiencing Them 11:03 Make The Date An Adventure 13:14 New Environments Create Natural Connection 14:47 Building Dates Around Your Life 16:20 Every Date As a Lesson 17:30 Self-Discovery Through Dating 19:25 Emotional Growth Through Lived Experience 23:00 Romanticize Your Love Life Again 28:00 Embracing The Beginning Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Hey, it's Jay. I don't know what your day's been like, but I was just thinking about you for a minute. And I hope you're being a little patient with yourself. because you deserve it. And yeah, I'll talk to you soon. I want to start today's episode by asking you a simple question. When was the last time you actually felt excited about dating? I mean, genuinely excited to just meet someone new, hear their story and spend an evening getting to know them. For a lot of people, maybe it's been a long time.

I know so many people feel burnt out, exhausted and just over trying to find their person. But if you're listening to this because you're about to delete the dating apps, all I ask is that you give me the next 30 minutes. And I will convince you how to get excited about your love life again. I know that sounds like a big ask, especially if you've been ghosted one too many times, sat through too many painfully awkward first dates, or found yourself thinking,

I just don't have it in me anymore. But before you decide that dating isn't worth it, before you convince yourself that maybe love just isn't in the cards for you, or before you accept that you're happier, giving up, then trying again, I want you to stay with me. Because I don't think you're tired of finding love. I think you're tired of the way you've been experiencing dating. And those are not the same thing.

If I ask you whether you still wanted someone to laugh with after a hard day, someone to build traditions with, someone to call first when something amazing happens, or someone to grow old beside, I don't think you'd hesitate for very long. Most people haven't stopped wanting those things, but what they've stopped believing is that the process of finding them can still be joyful.

Somewhere along the way, dating stopped feeling like an adventure and started feeling like an obligation. That's what I want to change today. Not because I have a perfect formula for meeting your soulmate. I'm sorry, I don't. And anyone who tells you they do is probably selling you something. But I do think that somewhere between dating apps, bad experiences, endless advice online, and trying so hard to protect ourselves from getting hurt,

we've accidentally forgotten what dating is actually supposed to be. Think about it for a second. On a first date, you're about to sit across from someone you've never met before. They have an entire childhood you've never heard about, friendships that shape them, heartbreaks that change them, dreams they're still afraid to say out loud, and stories you'll never know unless you ask. That's incredible. Somehow we've taken one of the most fascinating experiences life offers, meeting another human being, and turned it into a performance review on both ends. And look, I get why. When you've been disappointed enough times,

your brain stops looking for possibility and starts looking for proof that this one, won't work either. It's not its fault that it's trying to protect you. The problem is that when your goal becomes avoiding disappointment, instead of discovering people, dating loses the very thing that made it exciting in the first place. Curiosity. That's when every day it starts feeling the same. Every conversation feels repetitive, and every swipe feels like more work instead of another chance to be surprised. So that's my hope for you by the end of this episode. I'm going to take through four things you can shift right now in your dating life to get excited again about finding love. I don't just want you to leave this episode with better dating advice. I want you to leave

feeling hopeful again about meeting your person. And I want you to remember that somewhere in your city today, there are strangers living completely ordinary Tuesdays who might one day become one of the most important people in your life. And if by the end of this episode I've convinced you to open your hot, just a little wider, before closing that out forever, then I think it will have been worth it. For the first shift, I want to start with something I just mentioned, the role of curiosity. I think one of the biggest reasons dating feels so exhausting today is because we've turned it into a game of optimization. Everywhere you look, someone is teaching you how to date more efficiently. Your TikTok feed tells you the signs they're emotionally unavailable. Your group chat

analyzes screenshots of text messages like their criminal evidence. Dating apps encourage you to make a decision about someone in the time it takes to take a sip of your morning coffee. We have more information than any generation before us and yet so many people will tell you they've never felt more confused, more discouraged or more burned out by dating. The strange thing is none of these resources are inherently bad. I've shared advice on healthy relationships for years because I believe wisdom matters. Boundaries matter. Learning to recognize unhealthy patterns is extremely important. But every tool has a downside when we rely on it too heavily. If you're not careful, it's easy to start using dating advice as a way to turn the person sitting

across from you on that first date into a science project. You're analyzing them based on a million data points you've been trained to look for. So instead of walking into a date thinking, I'm excited to meet someone new. You walk in and put them under a microscope. Instagram teen accounts come with automatic protections that limit who can contact teens, the content they can see and the time they spend on the app. Learn more about teen accounts and Instagram's ongoing work to protect teens online at Instagram.com forward slash teen accounts.

I want you to think about what a first date actually feels like today. You're sitting across from someone you've never met before. But if you're honest, part of your attention isn't on them at all. It's in your own head. You're wondering whether there's chemistry, whether they seem emotionally available, whether you're attracted enough, whether your values align,

whether they're your type, whether you're wasting your night. Before you've even ordered dessert, you're trying to answer questions that no human being could possibly know the answer to after 90 minutes. And that's if you're lucky. You might end it in 30 to 60 minutes.

We've become incredibly good at evaluating people. I'm not sure we've become equally good at experiencing them. I think that's one of the costs of modern dating. Every interaction starts to feel like an interview. Every conversation feels like a test. Every date carries the weight of a decision it was never meant to make. No wonder people are tired. It's exhausting to believe every stranger has to immediately prove

whether they're worthy of becoming your future. What's interesting is that this isn't really how most of our other relationships begin. Think about the people who have had the biggest impact on your life. Your best friend, a mentor, a co-worker, every one of those relationships began with a stranger. You didn't meet them already knowing how important they would become. You didn't spend your first conversation deciding whether they'd still be in your life 10 years later. You simply met them. You talked.

You learned a little more the next time. then a little more after that. Over time, someone who meant nothing to you slowly became someone you couldn't imagine your life without. I sometimes wonder why we don't allow romance the same grace. Maybe it's because there's more at stake. Maybe it's because we've been hurt before. Maybe it's because we're afraid of wasting time.

Those are real fears and I don't want to dismiss them. But I also wonder whether our fear of wasting time has caused us to waste something just as valuable. The experience itself. We become so determined to figure out where a relationship is going that we never fully experience where it is. We rush toward the end because the end feels safe. But some of the most beautiful parts of life are hiding in the middle.

Human beings are incredibly difficult to understand quickly. The qualities that sustain great relationships, kindness, consistency, generosity, emotional maturity, resilience, don't usually reveal themselves

in the first 15 minutes. They've revealed themselves over time through ordinary moments, small conversations and repeated experiences. That's why trying to decide someone's entire future

in one evening is such an impossible task. This is where curiosity becomes such a powerful practice. Not because curiosity magically helps you find your soulmate, but because it changes the experience you're having while you're looking. Curiosity shifts your attention away from constantly asking,

is this my person? And towards asking, who is this person? Those questions sound similar, but they create completely different evenings. One puts pressure on every interaction, the other gives another human being permission to simply be themselves. And here's what I love about that shift. It doesn't just change your dating life, changes you. Curious people tend to move through the world differently.

They ask better questions. They have richer conversations. They leave interactions having learned something instead of simply having judged something. Because when you really stop to think about it, every conversation is an opportunity to briefly step into a world you'll never otherwise get to experience. I honestly think that's one of the greatest privileges of being alive. That's what makes life exciting and that's what makes dating exciting too. if we allow it to be. So before your next first date, I want you to try something different. Don't walk in hoping you'll have the answer by the end of the night. Walk in simply believing there's

something interesting to discover. Maybe you'll discover a perspective you've never considered before. Maybe you'll hear a joke you'll remember for years. Maybe you'll discover qualities that remind you what you truly value in a partner. Or maybe you'll meet someone who changes the direction of your life. You don't know yet, and that's exactly the point. I don't think the goal of dating is to become better at reading people and knowing what box to put them in. I think the goal is to remain open enough that life can still surprise you. If you prioritize curiosity, then no first day is ever a waste.

But I know you might be saying, Jay, no matter how open and curious I am, some first dates still just really suck. And I hear that, which is why I'm. I now want to hit on shift number two. You need to make the date itself an adventure. Have you ever noticed that so many first dates start to blur together? Maybe you leave work a little early so you have time to get ready.

You change outfits two or three times before finally deciding on something that feels like the right balance between effortless and intentional. You drive across town, walk into another wine bar or cocktail spot, and spend the first few minutes making polite conversation while you wait for the server to come over. Then you begin asking each other the exact same questions you've both answered dozens of times before. Where did you grow up? What do you do? Do you have siblings? How long have you lived here? What are you looking for? By the end of the night, you've learned a handful of facts about another person, but the experience itself feels almost identical to the last five dates you've been on. I don't think you're tired of first dates. I think you're tired of doing them all the exact same way.

Even if every person is different, the rhythm never changes. The setting doesn't change. The activity doesn't change. Eventually, daying begins to feel less like an adventure and more like a routine. But the moments we cherish most in our lives aren't usually built around receiving information. They're built around experiences. So why do we expect dating to be different? Imagine instead of the same bar for your next first date, you hit an outdoor movie you've been wanting to see all summer.

or a farmer's market you've never made time to visit. Maybe there's a hiking trail with a view you've heard about, a cooking class you've booked marked months ago, or a bookstore you've walked past a hundred times, but never stepped inside. Picture any activity that you've already been dying to go to, and now picture that same first date conversation happening there instead. Can you feel how different that is?

The experience was already worth having before anyone said yes. If the conversation is incredible, that's about. If there's chemistry, even better. But even if there isn't, you still spent your date doing something that made your life a little fuller. This episode is brought to you by Prime Video. Okay, huge news. Carrie is now streaming on Prime Video. It's a bold reinvention of Stephen King's bestseller from showrunner and director Mike Flanagan. You love how he explores themes of isolation, resilience, identity and belonging. Carrie is a story about what happens when someone doesn't feel seen, heard or valued,

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Psychologists have found that novelty has a powerful effect on the brain. New environments make us more attentive. New experiences pull us into the present. moment because our minds have to process what we're seeing, hearing and feeling. That's one of the reasons vacations often feel like they last longer than ordinary weeks at home. When everything is familiar, our brains stop paying close attention. When something is new, we're fully engaged. Think about the difference between sitting across from someone for two hours and walking through an art museum together. If you hate museums, I get it, but you get the point. Suddenly, the conversation doesn't have to

carry the entire evening because the world around you is helping. A painting reminds one of you of your grandmother's house. A photograph sparks a conversation about travel. You find yourselves disagreeing about what a piece of art means and end up laughing about it. You're no longer trying to manufacture connection. You're allowing it to emerge naturally because you're sharing an experience instead of just exchanging information. When a date is simply two people sitting at a table across from each other, it's not a date, it's an interview. It's all about performance rather than presence. It's all about impressing the other person rather than actually getting insight. I also think this changes something much bigger about your dating life. It reminds you that your life

shouldn't be on hold while you're waiting to meet someone. One of the healthiest mindsets you can have is deciding that you're going to explore your city, learn new skills, try rest of you. and collect meaningful experiences whether you're single or in a relationship. Dating simply becomes an invitation for someone else to step into a life you're already enjoying. That's a very different energy than expecting another person to finally make your life feel exciting. So here's something I'd love for you to try. Before you plan your next date, don't ask yourself, where should we go? Ask yourself, what have I been wanting to experience lately?

Maybe it's a jazz show, maybe it's paddleboarding, maybe it's a botanical garden you've driven past for years, maybe it's a food festival or a pottery class or a comedy show. Whatever it is, choose something that would make you smile even if you ended up going alone. Because I think that's the real shift. Don't build your life around your dates. Build dates around your life. When you do that, something great happens. Every date stops feeling like a pass or fail test. Instead, it becomes a chapter in a life you're already excited to be living. Some chapters will introduce you to incredible people. Some will become funny stories. Some will teach you what you're looking for. And every once in a while, one ordinary afternoon will become the story you tell for the rest of your

life about how you met the person you were always meant to find. Now there's another layer to how to change your mentality about dates. And that is going to take us to our third shift. We need to allow every date to make us better. I think one of the biggest reasons people give up on dating is because they start believing it's a waste of time. You go on a date that goes nowhere. You spend three months getting excited about someone who suddenly disappears. You invest a year into a relationship that ultimately ends and after enough experiences like that, it's easy to arrive at the same conclusion. What's the point? Why keep putting yourself through the emotional roller coaster if most dates don't become relationships.

Why keep making time in your week for people who might only be in your life for a few hours? I think those are completely fair questions, but I also think they're built on an assumption that isn't true. The assumption is that the only thing you're getting from dating is the possibility of finding your person. So if you don't find your person, you leave believing you've got nothing in return.

But what if we've misunderstood what dating is actually for? I think we need to remember that every conversation is also revealing something about us. Every date is teaching us who we are, what we value, how we communicate, what makes us feel safe, and what kind of love actually brings out the best version of ourselves. The person seeing across from you isn't just someone you're getting to know. They're also holding up a mirror. Because listen, we all think we know exactly what we're looking for, until we actually start dating. Ask someone who's been single for a while

what they want in a partner and they'll usually have an answer ready they'll say they want someone ambitious confident, funny, adventurous, successful we all have these lists in our heads because they're based on who we imagine will be happiest with. But then life has a way of challenging those assumptions.

You meet someone who's incredibly charismatic and you realize charisma doesn't matter very much if you never feel emotionally safe around them. You date someone who checks every box on paper, but every time you're together, you feel like you're performing instead of relaxing. Then someone else comes along who isn't your usual type at all, and for the first time in a long time, you notice how peaceful you feel just being yourself. You can't learn those things sitting at home. You can't learn them from relationship TikToks, personality tests, or reading another list of green flags. Those things can give you language that can help you recognize patterns.

but they can't replace lived experience. There are certain lessons your heart only learns by actually being in relationship with another human being. Sometimes you discover that what you thought was chemistry was actually anxiety. Sometimes you realize you've spent years confusing unpredictability with excitement. Sometimes you recognize that you've been choosing people

who need to be rescued because it made you feel needed. Those aren't lessons you think your way into. They're lessons you're. you live your way into. Time spent dating is never wasted if you allow it to be a mirror for the lessons you still need to learn. Think about anything else you've ever wanted to become better at. You wouldn't expect to become stronger without going to the gym. You wouldn't expect to become a great musician without practicing. You wouldn't expect to become confident at public speaking without giving any presentations.

Growth comes from repetition. It comes from trying, reflecting, adjusting, and trying again. Love works the same way. Every honest conversation makes you a better communicator. Every difficult conversation teaches you something about conflict. Every type of relationship reveals habits you didn't know you had. Every goodbye gives you a little more clarity about what you'll never settle for again. Now, that doesn't mean every experience is enjoyable.

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Cards issued by JPMorgan Chase Bank, NA member FDIC, subject to credit approval, terms apply. Some dates will disappoint you, some people will reject you, some relationships will end in ways you never wanted them to. I'm not trying to pretend those moments don't hurt, because they do, but pain and progress often happen at the same time.

time. It's possible to leave a relationship heartbroken and more emotionally mature than you were when it began. It's possible to be deeply disappointed while also becoming clearer about the kind of love you're actually looking for. Those two things can exist together. So maybe we've been asking the wrong question. Instead of asking, did this date lead to a relationship, maybe we should be asking, what did this date reveal about me? Maybe it should be. Maybe it should be, showed you that you feel most like yourself around someone who's genuinely curious. Maybe it helped you realize that you've been ignoring your own needs to avoid disappointing other people. Maybe it confirmed that you're finally choosing partners who bring you peace instead of chaos. Whatever

the answer is, you leave knowing yourself a little better than you did the day before. That's why I don't think dating is ever a waste of time if you do it intentionally. Because even when you don't find the right person, you're becoming a better partner. You're becoming more honest, more self-aware, and more prepared for the relationship you're hoping to build one day. Every meaningful conversation, every disappointment, every moment of vulnerability is shaping the version of you that your future partner will eventually meet. And I don't know about you, but that makes me feel hopeful. It reminds me that even when love feels slow, nothing is standing still. Every experience is quite preparing you for the life you're trying to create. So the next time you walk away from a date

thinking, well, I guess I didn't go anywhere. I want you to pause for a moment and ask yourself a different question. What did I learn about myself tonight that I couldn't have learned any other way? Because I have a feeling the answer to that question might make you realize that evening was far more valuable than your first thought. And that takes me to the fourth and final shift. I want to teach you how to romanticize your love life again. I think one of the biggest tragedies of modern dating is that we become so good at protecting ourselves that we've forgotten how to get excited.

We know how to spot red flags, we know every dating term, every attachment style, every rule about how long to wait before texting back, but I sometimes wonder if all that has come at a cost. Because somewhere along the way, many of us stopped looking forward to falling in love and started looking for reason why it probably won't work.

I don't say that to criticize anyone. If you've been hurt before, it makes perfect sense. Psychologists call it negativity bias. Once we've been disappointed, we naturally become more vigilant for signs that disappointment is coming again. The problem is, you're no longer meeting someone with wonder. You're assessing them for risk.

But just for a moment, I want you to think back to the very first time you ever had a crush. Most likely, you're thinking back to a time, time long before your first serious relationship. Think of the kind of crush you had when you were 12 or 13 years old, before you knew all the rules. Maybe you spent way too long deciding what to wear because there was a chance they'd be in the hallway that day. Maybe you analyzed every glance and every smile like it was the biggest story in the world. If they said hi, maybe your stomach filled

with butterflies. You'd replay a five-minute conversation in your head for the rest of the afternoon. wondering if they were thinking about you too. Looking back, it's almost funny how little actually happened. Maybe they walked you to class once. Maybe they borrowed a pencil. Maybe they laughed at your joke. That's it. And yet somehow those tiny moments had the power to transform your entire week.

The bus ride home felt different. The songs on the radio sounded better. You woke up excited to go to school because your world suddenly felt full of possibility. Nothing about your circumstances were objectively different. What changed was your relationship to the ordinary. A regular Tuesday became something you couldn't wait to experience because you never knew what might happen. And today, that fun, excited feeling is still accessible to you.

But you have to allow yourself to have those little crushes again. Because it isn't just excitement about another person. It's excitement about life. Suddenly the coffee shop isn't just a coffee shop. because maybe you'll run into them. You don't mind checking your phone because there's something you're hoping to see. You find yourself smiling at absolutely nothing

while you're driving home because your mind keeps replaying one small moment. The world becomes more colourful. I don't think we talk about that excitement enough. We spend so much time talking about whether someone is the right fit and we skip over one of the most joyful parts of being human. Having hope, having butterflies,

wondering what could happen next, those feelings aren't childish. They're proof that your heart is beating. They're proof that you're allowing yourself to imagine a future. And there's something incredibly courageous about that after you've been hurt. Maybe that's why we've been telling love stories for thousands of years. Maybe that's why we still cry at wedding speeches,

smile during rom-cons, and instinctively turn up the volume when a love song comes on in the car. Those stories remind us of possibility. They're reminding us what it feels like to believe that one conversation, one coincidence, one ordinary day could suddenly change the direction of your entire life. And the beautiful thing is that it's still true. No matter how burn out you feel right now, you are right now living in a world where tomorrow

is still capable of surprising you. That's why I don't want you to become cynical, even if you've earned the right to be. I want you to protect your standards absolutely. I want you to know your values and recognize what's healthy and what's not, but I also want you to leave a little room for wonder. Leave room to laugh too hard on a first date. Leave room to be excited when someone's name appears on your phone. Leave room to believe that the next chapter of your life might start tomorrow.

Sometimes it begins with the smallest, most ordinary moment, and only later do you realize it changed everything. Because at the end of the day, I don't think dating is just about finding the right person. It's about refusing to lose the part of yourself that still believes love is out there. And if you can hold on to that feeling, if you can protect your hope just as fiercely

as you're protected your heart, I think you'll discover that love isn't just something you're searching for. It's something you're entirely worthy of experiencing. So before you delete the apps, before you decide you're done with dating, or before you convince yourself that love just isn't,

meant for you, I hope you'll remember this. The goal was never to become better at predicting the future. The goal was to stay open enough that the future could still surprise you. Score on the date, text the person you've been talking yourself out of texting, let your friends set you up, say yes to the plans you almost cancelled, flirt a little, have a crush, laugh too hard, stay out longer than you planned. Let yourself feel butterflies without immediately trying to figure out whether they're your soulmate. Let yourself enjoy the beginning instead of rushing toward the ending. Because those early moments, the anticipation, the excitement, the wondering, the stories you tell your friends the next morning, those aren't obstacles on the way to love. They are love.

They're part of the experience and there's some of the most joyful moments we get to have as human beings. And maybe none of it leads to a second date. Maybe it turns into a fun story. Maybe it teaches you something about yourself that you couldn't have learned any other way. Or maybe without realizing it, you're walking into the first chapter of the story you'll tell for the rest of your life. The beautiful thing is that you don't know which one it is yet, and you were never supposed to. If we knew exactly how our stories unfolded, we would miss the magic of living them. So I hope you keep saying yes. I hope you keep choosing curiosity over certainty, experiences over expectations, growth over perfection and hope over cynicism.

Most of all, I hope you never lose the part of yourself that still gets excited to meet someone new because that's the part of you that believes tomorrow could be different from today. That's the part that still believes in possibility. And I promise you, as long as you can hold on to that, love will always feel like an adventure instead of an obligation. Thank you so much for watching. Remember, I'm forever in your corner and I'm always rooting for you.