It’s the 100th episode! And there’s no way around it; dating can feel like an unhappy repetition of the same disappointing, time-consuming and frustrating old experiences. Here are some wonderful techniques to bring you back to inspiration, courage and a wonderful sense of new direction – and perhaps even fun. In this episode, you’ll find the hope it sometimes feels like you’ve lost.

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Show Notes:


  • The Slow Part Of The Journey
  • Beautiful Forks In The Road
  • Becoming Your Inner Mentor




Today on the 100th episode of the Deeper Dating Podcast, I talk about all the difficult crossroads we hit on our dating journeys, and what to do to bring wisdom, guidance, and inspiration to those difficult moments. Stay tuned to the Deeper Dating Podcast.

Hello, everybody and welcome to the 100th episode of the Deeper Dating® Podcast. I’m Ken Page and I’m a psychotherapist. I’m the author of Deeper Dating and I’m the Cofounder of, which is a way for people to meet online in an environment that’s respectful, warm, and inspiring. Today in this podcast, I’m going to talk about that difficult period on the dating journey when we’ve learned new skills and gained new wisdom, but we haven’t found our partner yet. This week and in every episode, I’m going to share the greatest tools that I know to help you find love and keep it flourishing, and heal your life in the process, because the skills of dating are the skills of love. The skills of love are the greatest skills of all for a happy life. If you want to learn more about the Deeper Dating® path to real intimacy, just go to Deeper Dating Podcast. You’ll get free gifts and you’ll be able to see transcripts of every one of the 100 episodes, and I hope you enjoy that. Also, everything I share in this podcast is educational in nature. It’s not medical or psychiatric advice or treatment. If you’re concerned about certain symptoms or conditions that you’re experiencing, please do seek professional help. If you like what you’re learning here, I’d love it if you could subscribe and leave me a review. Thank you so much for that, and let’s jump in.

In the work that I teach in my courses, in my intensives, in my book, and in my life journey, something that just really hits me, I mean, of course what hits me, and this is something I say a lot, which is there is hardly a day that ever goes by that I am not humbled by my clay feet when it comes to intimacy. I’m not happy about the things that I see that I need to work on, but I am happy because I see them and I work on them, because they hurt me, because they cause me pain, and I know that there are things that I need to work on. I’m just kind of in a very ongoing way in my relationships, pretty committed to that, but really, every step of the intimacy journey shows us our clay feet. Every step of the intimacy journey brings up new questions. We’re constantly, and we should be constantly, pondering with a kind of awe of what our stuck places are. How the same patterns seem to happen again and again. How hard it may be to extricate ourselves from that, as well as all the other wonderful things about the love that we have and the connections that we have.

I think that we do a disservice on social media and elsewhere, where we celebrate how fabulous our relationship is and how fabulous our life is because we want to be teachers of how fabulous we’ve gotten, and how other people can learn from us, and get that fabulous too. That saddens me a lot because I think it’s those humbling moments that are the sacred ones. That’s where we build. That’s where we grow. In the dating journey, I spend a lot of time in my classes, teaching people what I think are the foundations of wiser dating. I say this all the time, what I teach these four stages of discovering, naming, and treasuring your CORE GIFTS, understanding in a deeper way your patterns of attraction, and what they can teach you, and need to teach you about the places where you don’t love yourself, and the places where you do love yourself, about your bravery in life, and actually being who you are and choosing people who treasure that. That’s all stage two.


DDP 100 | Dating Slog
Dating Slog: It’s the humbling moments that are the sacred ones. That’s where we build and grow.


Stage three is the bravery of getting out there in new and different ways, and having growth adventures in an ongoing basis in our dating lives, hopefully with help, hopefully with support. The fourth stage is the rewiring that has to happen as we enter, because when we do these steps, we lose our taste for relationships that chip away our sense of self-worth. All of a sudden, we are having relationships with people who are kinder, more available, less roller-coastery, more caring, and more interested. This happens gradually, but it happens, and then there is a whole rewiring when our attraction is not based on fear of abandonment but instead, fear of intimacy because we’re with someone who’s really present. There’s so much rewiring ongoing that needs to happen that’s rich and important, and it’s an everyday kind of thing. These are the stages of the journey.


The Slow Part Of The Journey


I think that when I teach people about CORE GIFTS, it’s so powerful and so liberating for people to understand that, especially when we do the deep intensive work. It’s such a liberating, wonderful thing that there’s just a great sense of hope, and then people see that they are beginning to meet different kinds of people, that maybe their field or their understanding of themselves is actually beginning to shift. That is also fabulous, wonderful, empowering and exciting. Then there’s kind of like what happens between then and when you find your partner. That can be slow-going and hard. There can be repetitions of so many sadnesses and so many lonelinesses. That’s a hard part of the journey in very unique ways. Every part of the journey is humbling. It’s both humbling and thrilling, good, and wonderful when we heal and when we grow. We discover new mastery, but it’s all humbling too. This stage where we’re looking, and it hasn’t happened yet, and it could feel like that’s going on for way too long, can be a really difficult stage.

I remember a dream I had once when I was fiercely, deeply into my intimacy journey, my desire to change the way that I date. I hope that for all of you, you are reaching a point where you can say, “I am deeply into my intimacy journey. I am learning, I am working on this, I’m really trying, I’m learning things, I’m changing.” If you can say that, there’s just such hope in that, but I remember very much being in that place of learning and growing, and very much still being single. I remember a dream I had. There was a couple that fell deeply, deeply in love. I was watching this in my dream, and they were kissing each other, and they were so deeply in love. I somehow ended up having this beautiful, dewy rose in my hand. This beautiful rose with dew on it, it was my rose.


Every step of the intimacy journey shows us our clay feet. Share on X


They were so in love and I handed them the rose, and they really appreciated it, then they were out of the dream. I was filled with bittersweetness and I just wept. I was glad that I gave them that rose, but I was just viscerally experiencing my loneliness. For me, that period where I finally let myself stop rushing and could feel my loneliness, I knew that was a sign of progress. That dream I knew was a harbinger of something new. I could feel, even though it hurt, that I was on my way. What I would want for all of you that are on this journey is that you feel like, “It’s not going as perfectly as I wanted. I’m not there yet, but I’m on my way. I’m growing and I feel progress. I’m learning lessons of authenticity, truth, kindness and revealing, and making better choices,” because that’s such a huge one, is the choices we make.

I say this a lot. We focus all the time on how attractive we are, and so not enough on our patterns of attraction. I’ve never done an episode like this before, where I just riff on the things that I think are important. I’m always a lot more prepared. You may have a different experience with this. I hope it’s a useful experience because the subject of what it’s like in the middle is such a big deal. Here’s maybe the greatest thing that I want to tell you, is don’t do it alone. Don’t do it alone. I used to love watching Sex and the City. I mean, these women were hitting up against their own brick walls again and again and again, but they at least got to have fun with each other and laugh and talk.

I know for me, I needed friends who could guide me. I’ve mentioned this before. I created a support group for chronically single psychotherapists. It was only a few of us, but these were very wonderful people. Each week, we would come in with our struggles, what was happening in our dating life, where we were getting stuck, you know that experience of again and again, “Damn, I am hitting up against the same walls. I feel inept and I feel stuck, and I feel inadequate. What do I do?” Each of us would speak and the other members would hold what we said with care, and with what I call “cupped hands”. In that being held, my friends would notice openings that I didn’t see, like when you have a giant knot and you don’t know what to do with it, but there’s one thread that you could pull at and create an opening. They would notice these openings and they would share them with me. I still remember how pivotal that was, and how that changed my journey and other people’s journeys too. Many people in that group are now married and in couples. It’s just too hard a journey to do alone, and it’s not a smart journey to do alone because we will, even with help, again and again and again, play out old patterns.

There’s pretty much no class that I teach where I don’t encourage people to have a learning partner, in my audio course, in my book, in my intensive. In fact, even on, when people fill out their profiles, I ask if they are interested in finding a learning partner, and there’s actually a special functionality where you can click to look for learning partners from anywhere who can pair with you, to take this journey with you and learn together, and grow together. I just can’t say how much I believe in the importance of that. Also, it could be a lonely journey, and this helps. It helps a lot. It’s kind of crazy actually to think that we can do this by ourselves, and so much of the education and the advice out there tells us, “Just change this, just change this, just change this,” but change is not easy. This is such a truth that we forget again and again.


DDP 100 | Dating Slog
Dating Slog: Intimacy is just too hard a journey to do alone. Find a learning partner so that you can work together.


Beautiful Forks In The Road


Every day, I wake up thinking I am going to get so much done. Every day at the end of the day, I think, “Oh my God, I got so much less done than my most conservative picture of what I could get done could even show.” I got done less than that. I’m 64 years old. I do this every single day. Change is not an easy thing. Rewiring is just not an easy thing. That’s something else I just want to talk about. I want to talk about the beauty of bewildering crossroads. How many times have you been in a situation in your dating life or your life-life where you’re like, “Damn, I am here again at this stuck place where I’ve done the same thing again,” or where, “I feel not seen, not heard, disappointed or betrayed, again. It’s happening again and I’m helpless because I don’t know how to stop this?” A bewildering point where you just don’t know how to behave or how to handle something, or you’re frustrated, resentful or angry. These are the intimacy crossroads that we experience, and they’re holy and powerful. Left to our own devices, whatever it is that our kind of inner kid told us is the best way to do this, push through, ignore other people’s needs. Only focus on other people’s needs and ignore our needs.

The tendency, the fierce, fierce wired tendency is to do the same things. When we’re connected with someone or when we’re connected with our own inner wisdom, and I’m going to lead you in a beautiful process for your crossroads in just a couple of minutes, but whenever we’re in that situation, it’s a place to deconstruct as opposed to push through in our old ways. I think that’s an act of intimacy greatness when at those crossroads where we’re triggered, stuck, bewildered, pissed off, hurt, irritated, whatever things we are, confused, lonely. We have an old pattern of how we’re going to get through that that just somehow has not really worked that great. We can stop and somehow deconstruct, like soften around that hardened pattern, get brave around the ways that we avoid, whatever it is that we can come to that crossroads and rest, think, connect, and find some wisdom. Find some wisdom and do it differently.

That’s magic. That builds the foundation for the life that we dream of, the life that we want. Such a rich thing these crossroads, and God knows, kazillions of crossroads, I do the same way, but those crossroads where I can stop and decenter, often by getting advice from wise, loving friends, or by doing this Inner Mentor Process, which is my favorite process in the world, and which many of you have done already. This is a crossroads process because again and again, when I’m at a stuck place, I do this Inner Mentor Process and I deconstruct my stuck place, and a breeze of wisdom comes in. I start to see the good there. I see the possibility. I see the potential. I soothe myself. I have a sense of grace, and then some wisdom pours in that’s just like essence of the best of me, and my ancestors, and the people that love me and support me, and my teachers. I can feel it. I can feel the goodness, the sweetness, the airiness, and the spaciousness of the insight that I am given when I’m at this crossroads, and I do the Inner Mentor Process, which I do pretty much every day, and I’d like to do a number of times every day. That’s a goal of mine. I would love to lead you in this process because this is a way to find a friend, and it’s the friend of the you that you were born to be. It’s a friend of the you that is soft, caring, wise, strong and grounded. It’s the you that people who love you get to see and feel at your best. It’s your magic place.


Change is not an easy thing. We have a fierce, wired tendency to do the same things again and again. Share on X


Becoming Your Inner Mentor


Let’s do this. I’d like you to just close your eyes and just take a moment, and just relax. If you’ve had me do this Inner Mentor Process with you before, awesome, let’s do it again. You’re going to get a different set of guidance. Maybe you’ll get the same set of guidance but it will land in a different way. Get comfortable. I’d like you to remember a time that you felt really comfortable in your own skin; healthy, solid, good, and positive. Just remember a moment, a time when you felt that way. Don’t look for perfection in the way that you visualize this because my visualizations are like Swiss cheese, like moments of getting it, big moments if not, big holes. That’s fine. I love visualization because I accept that mine are like Swiss cheese. Give yourself that grace and that freedom. Also, you don’t have to have the perfect memory, just a general memory and even just little moments of glimpse.

Do that and remember that very unique, good feeling of feeling right in your own skin. Now I want you to remember a time that you felt a deep and beautiful love. I would just ask that it not be like a memory that is traumatic, that traumatizes you, in other words, like someone who betrayed you. Even if the person is not alive and you might have sadness, but it still is not traumatic and it holds goodness, that’s a fine memory. A time that you felt filled with a big and great and deep love. It could have been a spiritual moment, it could have been in nature, it doesn’t matter. Just remember what that was like. Gently and graciously hold that memory. I think of it like a breeze with a beautiful scent. You don’t smell it all the time, but there are moments that you do, and then you just enjoy that. That’s how I’d like you to remember this moment, if that fits for you.

Just hold that to your heart what that’s like. Now I’d like you to remember a time that you were at a crossroads, and you deconstructed an old way of behaving, and handled it in a better way and felt really good as a result. A time you did something different. You pivoted from an old, not helpful way. You did something wiser and it worked that it was good. Remember what that felt like, just hold that memory. Now I just want you to imagine the you that lives that way, like a you that is the enlightened you, that lives in the flow of those feelings. It’s an imagination. You don’t have to be there yet. You just imagine this you. On some level, it’s so close to you. It’s like a sibling. It’s so close because you know that you. It’s you. It’s the you you’re meant to be. It’s the you unblocked. It’s the you beautiful.

Picture that you, imagine that you, full throttle, open, relaxed, present, essence of you. Now I want you to imagine that you become that you, just for the moment. It’s an imagination exercise, but it’s awesome, because it’s a practice to actually move toward becoming that you. Just imagine that you are that you, and that you actually step into that role. You step into the body, the heart and the face, behind the eyes of that you. In your guts, in your kishkes, in your heart, you’re you, in your fingertips. You are this you, and just feel and imagine what that’s like.


DDP 100 | Dating Slog
Dating Slog: In this slow, sluggish, confusing crossroads of dating, it’s wonderful to know that you can tap into a place of goodness, wisdom and guidance.


Now, look at the you of today. I want you to speak out loud if you can or write it down. You can pause this if you like, and just take some time to let the words and the wisdom pool, and then unspool, and come out. Just take some time to do this. Share whatever guidance you want with the you of today. Good. Now, imagine opening your arms and now you’re hugging each other, and it’s the you of today and the you that you’re meant to be, your Inner Mentor, your full, full self. What that’s like to hug each other, to feel the differentness and the sameness. Feel that lovely hug, slowly open your eyes, come back, and what you wrote, what you said is your meditation for the day. That’s your perfect, couldn’t be better, daily meditation. All you have to do is love this message. By loving it, it will change you. By doing this process, the more you do it, the more you’re going to get close and friendly, and become that Inner Mentor self.

I encourage you to use this in the slow, sloggy, confusing crossroads of dating, crossroads of all relationships. It’s so sweet and wonderful to know that you can tap into a place that has such goodness, wisdom and guidance. We need that guidance again and again. We need the kind, soft touch of caring guidance to help us steer right again and again. Thank you so much for listening to the 100th episode of the Deeper Dating Podcast, and I look forward to connecting with you in the next episode.


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