Today I talk about the biggest obstacles we face in our search for love and share tips on how to move past these obstacles. Recently, I asked 120 people to tell me about their struggles with finding lasting love. After hearing what they had to say, I noticed patterns emerging, so in this episode, I touch on the issues of exhaustion and hopelessness and how they affect our dating lives. I also give recommendations for online dating and explain why it matters that we study our own dating patterns. 

Listen to this episode to learn my best online tips and understand what you can do to stay optimistic while dating.

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Show Notes:


  • What are peoples’ key issues with finding love
  • Does Ken recommend online dating
  • What are the best online dating tips
  • Why do we need to study our patterns of attraction
  • How to keep your sense of hope while dating


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6 month coaching and mentorship intensive with Ken Page


The Biggest Obstacles to Finding Love -- and How to Move Past Them


Hello and welcome to the Deeper Dating Podcast. I’m Ken Page and I’m a psychotherapist. I’m the author of the bestselling book Deeper Dating and the host of this podcast, and I’m so glad you’re here today. 120 of my listeners and readers wrote to me to tell me their biggest stuck point, and I answered each one of them individually and learned so much from the process.

And in this episode, I’m going to tell you what people cited as their biggest stuck points and some of my thoughts and responses, and some of the amazing things that people said, as well. And before I get started with this, I just want to say that if you’d like a transcript of this or any other episode, just go to

And if you sign up for my mailing list, you’ll become part of my community of listeners, and you’ll get a free gift… actually a few free gifts and lots of opportunities to connect and learn more in different ways. And if you like what you hear here, I would really appreciate it if you could leave me a review and subscribe. And they’re just the most beautiful reviews and I’m deeply appreciative of that.


We look for love through intimacy, build skills around intimacy so that the journey to find a partner becomes an intimacy journey and there is just no greater treasure than that. Share on X


So, let’s jump in with this amazing stuff. I just want to start by saying that so many people thanked me, which I really appreciate, for the work that I teach, but also described shifts that they’re having as a result of really working with these ideas and implementing them and using them in their dating lives. And the two biggest ones, which mirror, I think, the two biggest ones that people experience are a deeper treasuring of their core gifts and a learning to lead with their core gifts in their dating life instead of hiding them, which we reflexively often do, and which this culture really kind of teaches us to do.


The Biggest Obstacles to Finding Love -- and How to Move Past Them

The biggest obstacles: a sense of hopelessness and exhaustion.


And the other is discrimination, really, really losing their taste for attractions of deprivation. And people described as well, a richer, deeper sense of self-love and self-treasuring. And I just want to read one quote that was just so gorgeously written by someone. This person said something really interesting. She said that she realized a momentous thing, “For the first time since she was a preteen she now has zero questions about her love life, none.

Happily single, and feeling so nourished and imperfect and equipped and filled with wonder about her personal journey toward the love of her life.” And then she said something very kind. She said, “Your work is a shining piece in the mosaic of how I’ve gotten to this new place after decades, plural, of such brutal, blistering deep heartache and fear that I’d never work it out.”


The biggest obstacles


There has been such rich eloquence in the things that people have described. So, now I would like to share some of the wounding places that… Because that’s what I asked for. I asked my entire community, the people that subscribe to my mailing list, I asked them to tell me the roughest spots for them, the places where there’s the most pain and the most complication.

And it was actually… I was surprised that I got 120 rich, rich responses, and I actually created voice messages for each one of those 120 people, which was really… I was a little overwhelmed, but it was fun and rich and delightful, and I learned so much from people.


Online dating apps drain us. Share on X


So, what I want to do is I want to talk about the issues that people described as their key issues. And then I want to share some of the insights that I shared with people around each of those things.
So the first, and one of the very, very biggest was a sense of hopelessness and exhaustion.

One person described it as discouragement fatigue from just too much disappointment and not enough rich, healthy, wonderful, hopeful things. So that was one really, really big one. And I have to say, so much of that was connected to online dating. So, I want to bring that one up as the next one. Like so many people saying I am so beyond exhausted by online dating, by the impersonality, the unkindness, et cetera.


The Biggest Obstacles to Finding Love -- and How to Move Past Them

Navigating online dating: I recommend a hybrid approach.


And I want to share a few thoughts about this piece of things. One thing I want to say is about online dating, and it is that I recommend a hybrid approach, maybe 33% each, maybe not. Maybe you’ll need to do more online dating, but here’s what that hybrid approach is. Online dating is draining. It is built to be gamified, and it is not built to be spiritually nourishing. It doesn’t invite goodness, decency, and care. In a way that’s a filter, because if you see goodness, decency, and care on these apps in someone’s behavior, it means that they are that person. That’s like something that they have curated and cared about and built in their lives.

But the hybrid approach that I recommend is online dating. And in that online dating part of it maybe be niche dating sites that kind of hit your particular interests and values. And then some of the behemoth dating sites as well. But the ones that allow you to put in a richer profile and do keyword searches around your interests and passions as well. So, that’s online dating, that’s one piece.

The other piece is an online activity that is not the online dating apps. It is looking for living, vibrant communities online; Facebook groups, other kind of groups of people who share your values and connect in those groups. They’re beautiful, beautiful 12-step groups. There are meditation groups. There’s so many different kinds of groups.

Finding a group with people who share your values and looking for ones with the gender or genders that you are interested in, the age range that you’re interested in, kind of targeting that and specifying that and looking for groups like that. And then if somebody interests you, you can look who they are on Facebook and you can find them in other places and get to know them more and then direct message them, et cetera. So that is number two.

And number three is in-person events. Believe me, folks, there is a magic that does not transmit easily in online dating and does so much easier in live events and live situations. Even if it means schlepping and going somewhere far away, I really recommend it. So that is a hybrid that I think everyone should kind of consider because you will be less drained by that experience. Online dating apps drain us. They really do.

Around the issue of hopelessness and exhaustion, which is such an understandable kind of part of this experience, I have a few things to say, but the biggest thing I have to say is this. There is this concept which is… It’s known as a fixed mindset approach. Like either you got it or you don’t. Either you got the magic or you don’t. Either you got the IT or you don’t. Either you know how to attract love or you just don’t. Versus a growth mindset, which is this is a skill-building process.

And if there’s anything I really want to share with you, it’s like how would this not be a skill-building process? And so my question for you is, are you in a skill-building process using a template, using an approach, using a philosophy, whether it’s yours or someone else’s, or a hybrid that rings true and wise and good and smart to you? Are you growing in your skills at working on the ways that you might consciously, unconsciously, or semi-consciously be pushing love away? Are you growing in that arena? If so, things are going to change.

Are you learning deeper lessons of love and intimacy? Are you learning to show your authentic self? Are you learning to discriminate, to more and more choose people who honor you for who you are and have goodness and consistency and decency? If the answers to these questions are “no, I’m kind of doing the same thing and hoping for different results”, well then you know the answer.

And if you are working on these things and you’re finding that these skills are growing – celebrate, celebrate, celebrate. Even if you haven’t found your relationship yet, this is a skill-building process. And the more you build these skills, the more quickly you’re going to move to love.

And it’s such a kind of unkind thing. It’s such a disservice that we are somehow told that dating is this IT thing. Either you have IT or you don’t, that you’re not supposed to be deeply learning and growing, becoming more brave, becoming more discriminating, becoming more authentic. All those are pieces of this skill-building journey. So that’s a really important thing.

And I want to read something fabulous that someone said in this process. She said, “This month I had a realization. Dating is a marathon, it is not a sprint. For this process to be sustainable for me I should let my disciplined part take over the process. The same part that gets me to work out even though I’m not thrilled about working out.”

Not the part that gets her hopes up and then crashes and burns. Rather the part that is not just looking for a reward but shows up out of discipline. But let that discipline not just be a discipline of getting out there again and again, but using the wisdom tools that you gain and living those.

That is one of the most powerful ways that we find the light in the middle of the tunnel, that we get through this slog is by the experience of I am growing, I am growing in my intimacy journey. That fills our heart, that gives us hope. And we need constant, constant microdoses and macrodoses of that hope as we take this journey because it’s a precious, hard, scary, lots of things journey.


Study the patterns


Other people talked about attracting the wrong people continuously. And that’s a subject that is very, very, very close to the heart of my work because I think that we need to become deep students of our patterns of attraction. For three reasons we need to begin to really notice all the patterns of our attractions of deprivation; the subtle patterns, the obvious patterns, the things we get attracted to again and again, for three reasons.

One, because we can tune our dial to learn to notice those things more quickly and say no to them more simply and more directly and get help in doing that when we need it. Because often those are very sexy and compelling attractions. They just really are.

The second reason is we can tune our dial to guide us toward the opposite relationships, what I call attractions of inspiration. And that’s this very fierce and deep thing. It’s something that we do as a really significant ritual in the intensive – is making a pledge.

And the pledge is that we are going to just say no, we’re going to press our back against that crowded, bustling door of interest in attractions of deprivation and only look for attractions of inspiration, where we get that fabulous, fabulous, amazing mixture of goodness, solidity and sexiness and love all together. That’s the golden, golden alchemical mixture that we are looking for. So it’s kind of really making that commitment.

The third reason is anytime there’s a pattern, it’s gold because it shows us something – the two things that I just mentioned, but also whenever there’s a pattern of being attracted to people who aren’t good for us, it speaks to a broken, hurt, missing or wounded part of us that is trying to find an answer in the wrong places. And we need to rescue that part.


We need to become deep students of our patterns of attraction. Share on X


Another thing that people mentioned many, many times is kind of getting over heartbreak. And I’ve talked about this a bunch, but people have said that they lost a partner or profoundly they were betrayed or abandoned or someone left them or cheated on them, and the relationship ended.

And people, I think we are often stunned at how long it takes to get over that and past it and how deep the wounds go. And what I said to people again and again in these messages was that as much as we want to get past this, it does sometimes take a bewilderingly long time. And people described having their hearts frozen and their walls up because of these experiences.


The Biggest Obstacles to Finding Love -- and How to Move Past Them

Study the patterns: we need to begin to really notice all the patterns of our attractions of deprivation, the subtle patterns, the obvious patterns, the things we get attracted to again and again.


And what I said kind of again and again, and this is from my own personal experience, is that what we need to do, I believe, is not push ourselves past our pain, but to hold our pain with kind hands and to say, “Yes, my heart is broken. It makes sense that my heart is broken. I’m feeling a wave of pain that’s like a knife inside of me. Yes, and I’m holding my heart with care. My heart’s hurting so bad and I’m holding it with cupped hands, with kindness. I’m there for my heart, but man, am I in heartbreak.”

And when we do that, something amazing happens when we stop resisting it, our heart softens and those walls are made of a kind of temporarily hardened parts of our heart. So when we hold our heart like this, the trauma begins to thaw, our hearts soften and we heal quicker. It’s counterintuitive because you feel like you should push past it, but this way of holding our hearts is just so important and giving ourselves that patience.


Staying optimistic


And the final thing I want to mention… There are many more, and maybe I’ll talk about them in other episodes, but the final one is kind of a fear of the next step. A number of people describe doing really rich personal growth work and building self-love and feeling like, “Oh my god, I have to go out into that cold world and date again, and I don’t want to, I just don’t want to.”

And what I have said to those people and what I deeply believe is like, “Yeah, I get it. It’s a huge step to build the self-love, and it’s an awkward step to move from that into the dating arena.” It really is. But it’s a step that when we’re ready, we really need to take. And the way to do it is with friends and with support, a supportive community to push us, to encourage us, to give us insights as we go along that kind of stumbly, hard, hard path of dating.

These are ways that we turn the journey to love, to find love, not into something transactional. In other words, like did we get the gold ring or not? But instead, a journey of hope and growth where the medium becomes intimacy. We look for love through intimacy. We build skills around intimacy so that the journey to find a partner becomes an intimacy journey, and there’s just no greater treasure than that.

The last thing I want to say is that in the midst of all of this difficulty… I asked people for their most difficult parts. The sense of hope that still existed, the sense of desire, the sense of longing for a relationship, it was so precious and so palpable.

So I want to thank all of you for listening. I’d love for you to comment, share your thoughts, share your experience. I’m so grateful to all of those around 120 people that gave me such rich insights. And if you haven’t joined my mailing list, just go to and join it there. Thank you all so much for listening, and I look forward to connecting on the next episode.


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