Today is all about how to get free from the quicksand of dating discouragement. Who is this episode for? Do you find yourself feeling tired of dating? Could you describe your feelings around dating as discouraged, jaded, or disappointed? If so, this episode is for you. In this episode, I explain how we can turn discouragement into hope. I offer practical tips to help you turn the search for love into an adventure of growth.

Listen in as I explain discouragement fatigue and offer advice on online dating.

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Show Notes:


  • What is discouragement fatigue
  • How to cultivate self-compassion
  • Why you should find a learning partner in the search for love
  • What are some online dating tips
  • How to stop beating yourself up


Important Links:



6 month coaching and mentorship intensive with Ken Page


How to Get Free From the Quicksand of Dating Discouragement


One of the hardest things in dating and looking for love is the discouragement and the disappointment that we can feel, and that makes us want to stop and that makes us want to pull back, but we know that we’re looking for love. How do we deal with that discouragement fatigue in our dating life? Stay tuned to this episode to learn real actionable ways to change, transform, and handle that discouragement fatigue.

Hello everybody and welcome to the Deeper Dating® Podcast. I’m Ken Page. I’m a psychotherapist. I’m the author of the bestselling book, Deeper Dating, which you can see right here, and has changed many people’s lives and has been a great gift to be able to write. I’m the host of this podcast, the founder of the Deeper Dating Intensive, and someone who has specialized in this work as a psychotherapist for many, many years.

I’m so excited to be here with you.

And today, I want to talk about what’s been coined “discouragement fatigue”. That experience of just being exhausted of dating; tired, jaded, discouraged, disappointed, and what to do with those feelings and how to shift them to help you get to your goal, which is a wonderful, loving relationship.


Find a community or a person or a coach with whom you can experiment and fail and pick yourself up and realize something really didn't work, and then look at it together and then think about and discover what does work. Share on X


But first, I just want to say that if you are interested in this Deeper Dating® approach to intimacy, just go to And there, you’ll find transcripts of all 165 or 166 episodes, as well as free resources and gifts and all of the episodes.

And if you do sign up for my mailing list, you will receive a collection of really beautiful and empowering gifts, including an audio meditation or personal journal, and an eBook. And if you like what you’re learning here, I would really appreciate it if you could subscribe and leave me a review on any of the platforms that you’re listening to me on.


How to Get Free From the Quicksand of Dating Discouragement

Turn discouragement into hope: shift that experience of discouragement into one where you feel yourself becoming more empowered, growing, making different choices, meeting different kinds of people, all of which bring in hope.


Okay, let’s jump in now. A number of months ago, I wrote to my entire mailing list and I asked them what was the biggest problem that they experienced in their search for love, what was the biggest sticking point, the biggest obstacle. And what they said, this was the number one, and somebody coined it “discouragement fatigue”, which I really love.

And as a therapist working in this field and in all of the many intensives that I’ve done, I think this is one of the deepest, hardest things, is that feeling of exhaustion and frustration and dehumanization and just the endless scars that we experience from the cold and unkind world of online dating, that just exhaust us and make us want to give up, even though we don’t want to give up because we’re looking for love. It really matters. But the experience of looking for love in ways that reduce our self-love and make us feel more hopeless is just a very, very difficult and complex thing.

So what I want to talk to you about today is some of the ways that I teach, that I’ve discovered, that I’ve used in my own life to turn discouragement into hope, to actually be able to shift that experience of discouragement into one where you feel yourself becoming more empowered, growing, making different choices, meeting different kinds of people, all of which bring in hope. So I want to share some practices with you to help you with that exhaustion and that fatigue, to actually turn it into a place of empowerment.


Learning to hold ourselves


So the first thing I want to say is I want to normalize and acknowledge that feeling of exhaustion. And I want to say sometimes we need to push through that and just act, but so often we need to hold it with compassion. These things hurt. One of the things that I’ve experienced is the people who experience rejection, like hurtful rejection from someone really special to them, or maybe not even that special, but the rejection just really hurt, it throws us for a loop. We fall, we falter, and we think we need to get up right away, and that anything less is a kind of weakness. I think we need to be kind to ourselves. There are periods we need to pull back and heal. There are times that we need to be patient with ourselves.

So I want to say that first, and I’m going to talk about that more later. But no, maybe I’ll talk about it right now, as the foundational skill for being able to deal with discouragement. And it is self-compassion. It’s being able to say, “I am hurt. I’m kind of despairing,” or, “I’m exhausted,” or, “I need a break.” And being able to admit that and hold it with gentleness.


We do so much better, it is so much more fun, the pain reduces more greatly when we are in connection. Share on X


This is one of the skills that I teach, and it’s what I call the skills of holding ourselves with cupped hands. It’s something I speak about a lot, but I’m going to say something about it right now. You can imagine holding yourself, and you could even do this with your hands if you want to try, because it’ll help make it more real for you.

Holding yourself with flat, objectifying hands, like, “Okay, what am I doing right? What am I doing wrong? What’s not impressive about my performance in the dating world? What do I have to fix? What do I have to change?” And it’s like looking at it with cold, evaluative eyes, and those are not the eyes that are going to sustain us on this precious, mysterious, and difficult journey of finding love. That’s flat hands.


How to Get Free From the Quicksand of Dating Discouragement

When we’re torturing ourselves, that spirit is not going to come out: one of the greatest skills of all in your dating journey is to hold your heart and your feeling with cupped hands.


The other thing is that you could take your hands and squeeze them together, and that’s this feeling of pressure. Time is limited, the clock is ticking, “My biological clock is ticking. I better get to work.” Or telling ourselves we need to lose this weight, we need to be different, et cetera, et cetera, which once again blocks the beauty of our spirit from showing and revealing ourselves.

And let me tell you, it is the magic of your presence and your spirit and your heart that is going to help you more than anything find success and find love and find the kind of love you’re looking for. And when we’re torturing ourselves, that spirit is not going to come out. Hence, one of the greatest skills of all in your dating journey is to hold your heart and your feeling with cupped hands.

And you could do that now. You could take your hands and just imagine that you’re cupping a baby bird, you’re giving it space, but there’s this cherishing feeling as well. That is how we must learn to hold ourselves on this really difficult journey.


 Practice the skill of self-compassion


In my intensives, we spend so much time working on this and helping each other to do that, to go back to cupped hands when it’s so easy to just blame ourselves or judge ourselves. So I want to say that first, that the act of self-compassion is so important, so, so, so important. And you might even take a minute now, pause the recording if you like.

What would be holding yourself with cupped hands? How would you be with yourself now? What would it be like if you practiced the skill of self-compassion, of cupped hands in your dating journey? Think of what you’d be like.

And the other thing that I want to say about that is not only does that make it easier, it tunes you into your beauty, to your goodness, to your patience, to the part of you that you love and the part of you that is able to love. So just growing that skill eases pain, brings joy, brings meaning, and connects us with the most beautiful parts of ourselves.

And those are the parts that we want to be able to be in touch with in our dating life. And I am not minimizing how hard this is and how there are times we just really need to pull back or cry or get support. And I believe in all of that.

And that’s the next thing I want to say, and research backs me up on this, the two things that are kind of the most central in your search for love, if you want to kind of succeed, which success and the feeling of change and growth, those are some of the greatest, greatest things to help us mitigate that sense of discouragement, “discouragement fatigue”, woundedness, rawness, is the feeling of like, “Damn, I’m doing this different. I am meeting different people. I am feeling different about myself. I have shifted my intentions in my search for love,” and I’ll talk about that more a little bit later. But when we can do that, the hope comes back, the discouragement recedes, and we’ve given a great, great gift to ourselves.

So two powerful things to make that happen. One, find a map that you believe in. Find books, find teachers, find an approach that rings true to you as an approach that heals, honors and leads you to healthy love, as opposed to any kind of gimmick based, or “you’re not enough” based approach. Find a template like that. This is one of them, and there are many others as well.

And then, find a community. Whether it’s one person, a learning partner, and all of my work encourages people and is actually built to have people have learning partners. My intensives, my book, my audio course, everything is because we do so much better, it’s so much more fun, the pain reduces more greatly when we’re in connection. So that’s the other one, find a community or a person or a coach with whom you can experiment and fail and pick yourself up and realize something really didn’t work, and then look at it together and then think about and discover what does work.


By turning this into a wisdom journey, you heal your heart, you speed your path to love, you learn the deep skills of love, and you become more the person you're meant to be. Share on X


There’s something about that that we access the source of our wisdom. Our wisdom starts to bubble up in that kind of connection in ways that if we were left to our own devices and our own mind wouldn’t happen. And the research backs this up just completely, completely. So that’s another thing, find a learning partner. Find someone who is single, who wants to do the conscious work, who is kind and who is consistent, and has your best interests at heart.

You can actually go to and fill out a profile there. It’s a site that I and my husband have created, and there you can actually search for people who are looking for other learning partners.

Here’s another thing. See if you can, and I’m going to tell you some ways that you can do this, turn this into an adventure. Because damn, it is an adventure. It is an adventure of learning. It is a mountain to be climbed with all of the brutal difficulty and the occasional glorious views that you can get, but turn it into an adventure.

And how do you do that? By turning it into an adventure of growth. So how do you do that? How do you turn it into an adventure of growth? Well, one thing that you need to do, I believe, is to stop relying so intensely on online dating, and I am all for online dating.

And for some people, because of distance or disability or lots of different possible reasons, online dating is one of the only ways to meet people. Please know that I am all for that, but for those of you who can, create a hybrid.

Don’t just lean on online dating, which is so easy and so seductive and built to be that seductive, and I’m going to say more about that in a minute. But don’t just rely on online dating, have a hybrid, and let the hybrid be online dating and try different kind of sites.

Don’t just do the swipe sites. Do sites where you can actually do keyword searches for the values and the things that matter to you. So, use different sites. There are niche sites that really, really specialize in vegetarians or bicyclists or whatever your interests are. And so, that’s one thing. Try different ways of approaching online dating.


How to Get Free From the Quicksand of Dating Discouragement

The search for love is hard on its own because so much dating culture sculpts bad behavior: by turning this search for love into a wisdom journey, you heal your heart, you speed your path to love, you learn the deep skills of love, and you become more the person you’re meant to be.


The second thing is look for online communities that are not online dating, Facebook groups, et cetera, et cetera, professional groups, communities of people who share your values. And then you can learn more about who the members are and some of them you might develop something with. That’s a richer way to connect because the more you connect based on shared values, the quicker your search goes, the more easily you meet people who you connect with.

This does not, according to research, forecast that it’s going to be an ultimate love relationship, but it does forecast some kind of connection. So why not start with that?

And the third way is in person, in person, in person because your magic comes through in person in a way that it doesn’t in other ways. So those are the three kind of branches of this hybrid approach that I really recommend.

The fourth one is be in your heart and be in your connectedness and look at people and smile at people in Starbucks, on the street. Now for women, this may not be something you want to do, probably isn’t something you want to do. But I mean, I guess a kind of open attitude and open atmosphere is good for anybody. So yes, be careful, be careful, but also see if you can be open, and if someone smiles at you, then you can notice it and you can communicate with people. And there’s your magic that comes out in your day-to-day life that I really think is a very beautiful and important thing.


Turn the dating search into an adventure


So this is scary stuff, but it’s an adventure. It turns this a little bit more into an adventure. If there’s someone who interests you, see if you can be brave enough to approach them. It is scary, but that scariness actually heightens Eros, heightens self-awareness, and it’s just something I really, really believe in.

I’m going to say something now about online dating. What I’m going to say is that I am going to ask my audience, and I want to ask you, what have you done that has helped you stop “discouragement fatigue” or mitigate it in your online dating? What tricks, what tools, what wisdom hacks, what practices have helped you?

I would so appreciate it if you could write and comment and tell me, and I’m actually going to be doing a special workshop for all the people who actually respond to that and share their ideas. So we’d really appreciate it if you could, if you’re on my email list, respond to my emails, and get on my email list if you’re not, respond to the email and let me know your ideas, your tricks, the things that you’ve done so that I could share them, and so that I could also have your email address so I could invite you to this special class for the people who respond.

I have a dear friend who taught me a wonderful adventure trick, and that is to make an intention for yourself. Every time you do online dating, every time you go on a date, every time you go into an environment where you might be meeting people to date, or even a live dating event, to actually set an intention that matters to you, that is going to define your success. Superceding, “Did I meet my one? Did I follow through on this intention?”

And the intention might be no matter what you’re not going to beat yourself up. The intention might going to be you’re just going to notice if you judge yourself and judge other people, and just be aware of how that feels. If you can’t not beat yourself up, then you can say, “I’m going to notice how I beat myself up,” and here’s an amazing, amazing practice that has worked powerfully for me.

If you’re someone who beats yourself up and you’re in an event where you can maybe tend to do that, separate yourself and write down all of the critical thoughts that you thought about yourself and other people. This is one of the things of the truth will set you free, but first, it’ll make you miserable. It’s shocking to do, but it is so liberating, because once you see the crap you tell yourself about you and about other people, it kind of loosens the stickiness of these horrible kind of things that we say to ourselves. So that’s another practice. That’s an intention that you can do.

Another intention might be that you are going to notice people who smile at you. Another intention might be that you’re not just going to look for the person you’re going to date, but you’re going to be open to meeting a whole range of new and different people.

Any of these intentions shift us from that horrible place of like, “Was it a success – I met someone who could be my one? Or was it a failure and maybe was I a failure because I didn’t?”

So last idea or two that I am going to mention that I think are so important, one is if you can tap into your wisdom, and you will do that if you have a learning community, a template and a map that you’re following, and if you have any practices that help you tap into your wisdom, episode three of Deeper Dating® Podcast is the inner mentor practice. It’s a practice I do every day. It helps you bypass your inner critic, connect to your inner wisdom and your sense of self-love.

When you do that, when you do practices, especially not just general meditation, but practices specifically related to your search for love and your intimacy life, when you do that, it might not happen immediately, but you get whispers of your organic wisdom.

All of a sudden you realize, “Oh, I could have been softer there. I could have been kinder,” or, “Wow, there was this really nice person and I didn’t notice them because I was so fixated on that unavailable person,” or whatever the wisdom bubbles are that you have. Those are your magic. And when you get those wisdom bubbles, when you follow them, you are turning your search for love into an adventure. If you’ve got someone you can share those stories with, so much the better.

In my intensives, that’s so much of what we do. We practice, we experiment, and we come back with our stories of what’s different. And I am going to share one fabulous practice with you now to help you in your thinking about your dating life.

And this practice is that every time you are thinking about your dating life or you’re going to go into an environment where there’s going to be some date-y kind of thing, or potentially so, think of five things that you have done that have been progress for you, that have been more wisdom, more connectedness. List those five things. This will help you kind of connect to your inner core of wisdom, capacity, and hope.

The search for love, oh my God, not only because it’s hard in its own, but because so much dating culture sculpts bad behavior, unkindness, pain, and disappointment, and superficiality, for all of those reasons, this is not easy. And it’s not easy just because it’s not easy. By turning this into a wisdom journey, you heal your heart, you speed your path to love, you learn the deep skills of love, and you become more the person you’re meant to be.

So thank you all for listening. I would love you to write to me and tell me your ways of dealing with this discouragement with online dating, particularly tools that you’ve used. Please write to me too and let me know how this is working for you. Sign up for my mailing list. And I’m just so happy to have you in this learning community, and I wish you all the best, and I’ll see you in the next episode of the Deeper Dating® Podcast.


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