And How Does That Make You Feel?

EP 308 — The Biggest Problem in Modern Dating

Jack Heyworth Episode 308

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Is the biggest problem in modern dating really dating apps, ghosting, and situationships—or are those just symptoms of something much deeper? In this episode, we explore why so many people struggle to build meaningful relationships despite having more opportunities to meet than ever before. Learn how fear of getting hurt can quietly shape the way we date, why emotional self-protection can become a barrier to genuine connection, and how modern dating culture has changed the way we approach trust, vulnerability, and commitment. If you’ve ever felt frustrated, burnt out, or disillusioned by dating, this episode offers a deeper psychological perspective on what’s really getting in the way of finding lasting love.

SPEAKER_00

Hello and welcome back to and how does that make you feel an Awaken podcast. I'm Jack, the therapist and founder of Awaken Online Therapy, and I want to start today's episode with a bit of a bold statement. I don't think the biggest problem in modern dating is dating apps. I don't think it's ghosting, I don't think it's situationships, and I don't even think it's commitment issues. I think all of those things are symptoms of a much bigger problem. Because if you ask people why dating feels so difficult today, you'll hear lots of different answers. Some people blame social media, some people blame dating apps, some people blame memes, some people blame women, some people blame an entire generation. But after years of working as a therapist and listening to hundreds of people talk about their relationships, I think the biggest problem is much simpler than all of that. I think the actual problem is we've become incredibly good at protecting ourselves during dating, but not very good at connecting with each other. And while protecting yourself is of course important, there comes a point where protection starts costing us the very thing it was designed to preserve real connection. So today I want to explain why I think that's happened, how it shows up in modern dating, and what we can do differently. Because I genuinely believe that if we can understand this one issue, so many other dating problems suddenly start making sense. So let's start with something I hear all the time. People say they want a relationship. They want someone consistent, someone kind, someone emotionally available, but at the same time they're terrified of getting hurt. Now that's understandable. Most adults have experienced heartbreak at some point in their lives. Maybe you've been cheated on, ghosted, rejected, led on, or had your trust broken. Those experiences, of course, leave a mark. The problem is that many people unknowingly take those experiences into every new relationship. Instead of asking who is this person, they're asking how is this person going to hurt me? And that's a completely different mindset. You're no longer exploring a connection, you're scanning for danger. And when you're constantly scanning for danger, it's very difficult to relax enough to let somebody genuinely get to know you. And that all happens because sometimes we confuse protection with strength. Now don't get me wrong, boundaries matter, self-respect matters, learning from past experiences of course matters. But somewhere along the way, I think we've started celebrating emotional distance as though it's emotional maturity. People are encouraged to never text first, never look too interested, always keep their options open, never care too much, leave before they get left. It's almost as if caring has become something to hide. But here's the irony. And that's because vulnerability involves risk. There is no version of love where you get complete certainty before you open your heart. If there was, it wouldn't really be vulnerability. The next thing that appears to be a problem in modern dating is we're judging people before we know them. Modern dating encourages us to make incredibly fast decisions. Within minutes we have to decide whether someone is attractive enough, interesting enough, funny enough, successful enough, compatible enough, sometimes before we've even met them. Now first impressions matter. I'm not pretending they don't. But relationships aren't built on first impressions. They're built on repeated experiences. Think about the people you're closest to. If you'd only met them for five minutes, would you know everything you love about them? Probably not. You discovered those things over time, yet modern dating often expects us to know whether someone is right after a handful of messages or one coffee. Sometimes we're walking away from people we simply haven't given enough opportunity to become known. The next challenge is everyone wants certainty before commitment. People want guarantees. They want to know will this work? Are they the one? Am I wasting my time? Will I get hurt? Unfortunately, relationships don't come with guarantees. You can choose someone wonderful and still experience heartbreak. That's part of loving another human being. The goal isn't finding certainty, the goal is finding someone who is willing to build something alongside you despite the uncertainty. Healthy relationships are not built because two people knew it would definitely work. They're built because two people decided it was worth trying. The next thing, we've forgotten that relationships grow. I think social media has quietly changed our expectations. We've been shown highlight reels, perfect proposals, perfect holidays, perfect anniversaries, perfect couples. Very rarely do we see the difficult conversations, the compromises, the misunderstandings, the repairs. And because of that, people assume that healthy relationships should feel effortless, but they don't. Healthy relationships still require communication, patience, forgiveness, adjustment, and growth. The difference isn't that healthy couples never struggle, it's that they struggle together instead of against each other. So what is the biggest shift we need to make? If protection has become the biggest obstacle to connection, what do we do? I don't think the answer is becoming naive or trusting everyone or ignoring red flags. The answer is learning the difference between guarded and being wise. Wisdom says I'll pay attention to behavior. Fear says I'll assume the worst. Wisdom says I'll build trust gradually, and fear says I'll never let anyone get close to me. Those are very, very different ways of approaching relationships. One protects your well-being while still allowing connection, the other protects you from pain, but often protects you from love as well. So if you do take one thing from today's episode, let it be this. The biggest problem in modern dating isn't that people don't want love. It's that many people are trying to find love while protecting themselves from every possibility of being hurt. And sadly, those two goals often pull in opposite directions. Because every meaningful relationship asks something of us. It asks us to trust, to communicate, to be vulnerable, to risk disappointment. Not recklessly, not immediately, but eventually. So if you've been feeling frustrated by modern dating, maybe ask yourself the following question. Am I protecting my heart or am I building walls around it? Because there is a big difference. Healthy boundaries have gates. They let the right people in over time. Walls, they keep everyone out. And if we're serious about finding meaningful relationships, perhaps the goal isn't to remove all risk. Perhaps the goal is simply to become wise enough to recognize the people who are worth taking that risk with. As always, thank you so much for listening. And if you have found this podcast useful, feel free to share it with a friend or even rate us five stars on your streaming platform of choice. It really does help us reach more people, and we are going to be posting every single day. I've been Jack, and this has been And How Does That Make You Feel an Awakened Podcast, and I look forward to seeing you at the next one.