Our intimacy journey is the greatest journey of our lives. There are three stages that comprise this journey, and in this episode, I explain each of them. By the end of the episode, you’ll know which stage you’re in, and what you need to do to move forward to the next. Discover the three stages of dating, and how to navigate them to find love.

If you love the Show, please Subscribe, Rate, Review and Share on Apple Podcasts, or your favorite Podcast Platform!

Deeper Dating on Apple Podcasts



Stage 1 occurs when you learn to let go of people and situations that chip away at your sense of self-worth. When that happens, everything begins to change.

Stage 2 is that in-between space where you’ve lost interest in people who aren’t available, aren’t healthy or don’t treat you right—but the new generation of people just hasn’t arrived yet. We’ll talk about how to make the most out of this awkward stage—and how move out of it more quickly!

Stage 3 occurs when our dating lives begin to populate with people who are safer, more available, and who are able to love us for who we are. There’s a whole different rule-book for these relationships, and you’ll learn about it in this episode.

The 3 stages have a kind of epic quality because every one of them is so big and changes us in such deep ways. And, as you take these three steps in your life, it’s going to move you forward toward a more loving life, a richer life and toward romantic love–the romantic love that you seek–because the greatest lessons of dating are the lessons of true intimacy. And the lessons of true intimacy are the greatest lessons of our lives.

You may find one foot in each of the three stages of deeper dating, but just use this to identify where you are in your journey, what you’ve come through, what you’ve learned, and what’s next for you. And for each of these stages, I’m going to give you examples to help you understand more fully, and I’m also going to tell you how to move through the stages more quickly and how to use them more effectively to enrich your entire intimacy journey.


Stage 1 – Finding Your Sense Of Self Worth


Three Stages of Deeper Dating - Stage 1 Finding A Sense Of Self Worth


The first stage of the three stages of deeper dating is really quite an amazing stage. It sometimes even has a majestic quality, and it’s not easy to come by. But at its heart, this is the stage where we begin to lose our taste for people and relationships and situations that chip away at our sense of self-worth. When that happens, everything begins to change. Here’s a quote from my book Deeper Dating about this first stage:

“At a certain point, and usually as a result of tremendous pain, we’ll begin to lose our taste for relationships that chip away at our sense of self-worth. We find we just can’t stomach the thought of being hurt like that again.”

The end of a dead end era

When we become less sticky to these kind of attractions, a dead end era of our dating life is finally coming to an end. Now we can begin the real work of intimacy, cultivating our attraction to relationships that feed and nurture us. In dating, and in all of our relationships, we start to clean house, emptying our lives of unnecessary interactions with relationships of deprivation.

At its heart, this stage is where we learn perhaps the greatest lesson of love. It’s the lesson we’ve all heard countless times, but it is not easy. It is to be ourselves. But that is no simple thing. Because who we really are is loaded with qualities of sensitivity, of passion, of uniqueness, of differentness, that have gotten us hurt in the past.

Finding our most authentic selves

If you imagine the image of a target, and if you imagine that the closer you get to the center, the closer you’re getting to the core of who you really are; your very soul, the places where you care the most. And we know that the places we care the most are the places where we can be hurt the most. And these places are the home of the most authentic us.

But because people take advantage of those qualities in us, and because were never taught how to understand our unique geniuses, these qualities–so unique and so different, so tender and so passionate–sometimes feel not like gifts but like curses. People take advantage of them, step on them, and neglect them, so we learn to cover them up, and we create a false self. Now here’s the amazing thing:

When we live by our false self, we become attracted to people who step on us, people who chip away at us, people who can’t love us.

Why that’s true is a subject for a future episode, but it is true. And in this stage, what happens is that we begin to excavate these qualities and learn how to honor them and cherish them, we learn how to dignify those parts of ourselves that are uniquely us. And it’s one of the holiest, greatest, the most powerful parts of our intimacy journey.

Learning to cherish ourselves

In my work teaching this kind of approach, I’ve seen countless people learn the process of cherishing these parts of themselves that they were once ashamed of, and embarrassed by. Maybe qualities of generosity; for example, someone who, let’s say, has been successful in their lives and has a generous heart, and is giving but found herself giving as a way to win love–from people who couldn’t give in the same way back, not necessarily financially, but in any way. And so they realize that their abundance has been taken advantage of.

Or another example of that is a kind of generosity of spirit. It might not involve financial or material abundance, but might involve just the kind of person who loves to give. If you’re someone who loves to give, God forbid you don’t know that your people need to be people who love to to give back, because you will waste your gifts in the most painful ways on people who just milk that quality of yours.

So people with that kind of generosity need to stop and need to learn to honor and dignify that quality, and realize that not everyone has that quality, that their people and their tribe are those people that treasure that part of them and know how to give it back. This is how we learn to dignify our most authentic qualities. And when we do that, our attractions begin to change.

Leading with our soul

Chip Conley, a dear friend and best-selling author of the book Emotional Equations and Wisdom at Work, said, after reading Deeper Dating, that in his mind:

The key to finding a soul mate is simply to lead with your soul.

And that just means leading with your deepest, truest self, the part of you at the center of this target, the core of you. And, in order to lead with our soul, we need to be able to dignify our soul, the core and the heart of who we are, and that’s what happens in this stage.

And when that happens, when we begin to honor what I call our “Core Gifts,” these qualities of deep authenticity, of tenderness and vulnerability, of generosity, of passion, when we learn to honor these qualities that, maybe we’ve been ashamed of or, haven’t known how to honor before in the past, something amazing thing happens: We lose our taste for those people with whom, we feel like we have to prove our worth. People who we have to ask them again and again to be available–which ultimately they can’t really do.

Start honoring your best qualities

So in this first stage, as you learn to dignify the qualities that are the most authentically you and learn to stop saying, “Well, I’m just too sensitive”, and to begin to think, “I’m deeply sensitive.”

Stop thinking, I keep getting taken advantage of, what’s wrong with me and start thinking I have qualities of generosity that are profound and I need to honor them and take care of them.

Stop thinking, Why do I always end up with people that are unfaithful, and start thinking, loyalty matters to me deeply, to me it’s a core gift of mine, it’s an important quality and I’m going to finally learn how to honor and dignify that. When we do that, everything changes.

And that’s the first stage, and I’ve seen it happen with so many people in their intimacy journeys. They begin to learn to treasure who they are, instead of constantly working on how they have to fix themselves, or improve themselves, or live out of self-doubt. When people do this, they lose their taste for negative attractions and they start to clean house. And that is a really wonderful and powerful thing. And when it happens, the field begins to change. As you lose interest in those people, they kind of just stop coming around. You somehow feel less sticky to them, and you find that they kind of gradually disappear out of your life.

Learning to let go

Now, the later part of this work becomes more difficult because, especially in romantic attractions, it’s so easy to be deeply sticky to those relationships. You can kind of picture a child holding a shard of broken glass and they don’t want to let go of it because to them it’s beautiful, but you as the adult see that it’s going to cause them a lot of pain as it cuts into their hand.

That’s what we’re like when we don’t want to let go of these unhealthy relationships.

So how do we move quicker through this first stage?

How do we deepen it, and strengthen it, and move quickly through it, so we can enter into the second stage? Well, there are a few different ways.

One way is to avail yourself of teachings that teach you how to honor who you are, that aren’t constantly telling you if you want to find love, you have to change this part of you, you have to change this part of you, you have to make yourself more attractive, you have to act more confident.

You want teachings that in the most essential way teach you to honor who you are in your intimacy journey, because I promise you–nothing else is going to work.

Finding a tribe

The second thing that you need in this stage to develop, little by little, is to find your tribe. Who is your tribe? It’s the people you honor and admire. And it’s the people who know how to cherish those qualities of you that you’re just learning how to finally dignify and honor and cherish. Those people are the heart and soul of a happy life.

And usually we have to start with friendships because it doesn’t happen as quickly sometimes with dating. Usually we have to kind of find those friends, find that tribe of people, and as we do that, we move through the first stage. But if you are somewhere in that first stage, celebrate, because it’s a path of bravery and it’s moving you to the next stages of your journey.

Until stage one happens–until we learn how to say no to unhealthy dynamics and unhealthy relationships–we are going to remain stuck.

Not throwing out the baby with the bathwater

But let me just add one more thought, for everyone who is saying Yes, I relate to this stage. In this stage, we often need to make a lot of changes in our current relationships. And I want to encourage each of you not to throw out the baby with the bathwater, with people who care about you, and love you, who maybe had dishonored these parts of you. It’s worth it, now that you’re finally beginning to dignify them yourself, to educate the people you love on how you need to be treated.

Around your Core Gifts, you’re going to be triggered more easily, you’re going to be sticky, you’re going to be vulnerable. It either can be hard to talk about them or hard not to overreact when you feel hurt in these arenas. So there’s a process of maturity that involves “saying what you mean, meaning what you say, and not saying it mean” as you try to heal relationships in which, for too long, you’ve gone along with ways that your Core Gifts were dishonored.

What I’m saying here is give it patience and give it time. Give yourself a chance and give the people you love a chance. Unless they’re being actively abusive, and then you should have no interest at all. So that’s stage one.


Stage 2 – Waiting For The Right Doors To Open


Doors Opening In Three Stages Of Deeper Dating
Stage two of the three stages of deeper dating can take longer than expected


Stage two is a kind of odd and unexpected stage and one that took me a really long time to be able to see in my clients’ lives. It’s a stage where it seems like not a lot is happening. It’s like you’ve cleaned house and now your house is kind of empty.

Another example would be if you picture a corridor, with doors on both sides of the corridor. And let’s say on the left side of the corridor are the old relationships that didn’t work for you and didn’t really feed you. And those doors are closed now. And on the right-hand side of the corridor are the new relationships, the new life you’re wanting that’s full of really healthy nurturing love. But that door hasn’t really opened yet and you kind of in the middle in this odd hallway.

And what’s so strange about this stage is it tends to last a lot longer than you picture it would. And it’s bewildering because it’s kind of empty. So why is that, that the strange second stage, where things just feel kind of like too quiet or too empty, exists and takes place?

We need time to heal

Well, one reason is that we often need time to heal. Our our brains might be saying I want what’s next, but our psyches are saying, oh my God, I need to rest. I need to repair myself here. I need to lick my wounds. I need to reconfigure.

And this is a deep stage. So much of what’s going on in this weird second stage is happening underground. Our psyches need time to reconfigure. You know, the story of Passover is the story where the Jews left generations and generations of being slaves to the pharaohs. And they finally escape, and you would think that they escape and they enter into a new land, but they don’t. They spend 40 years in the desert, lost, because they’re not ready yet to enter into the new land, because it’s too scary. It’s too different. There might be giants there. They don’t know what’s there. And in fact that generation has to kind of die off before the new generation finally enters into the new land.

Compassion for ourselves

And so we need to have some compassion for ourselves because deep down our insides are not stupid, and they’re protecting us, and they know that we have not been able to protect ourselves against bad relationships well enough in the past. So they’re not going to be stupid and just allow us into this new land.

The great psychological theorist Winnicott says that all of us have a true self.

But that self is so precious and so central to our being that in order to protect it, we need to create a false self so that people don’t decimate our true selves. We create a false self to protect ourselves. And what Winnicott says is that the importance of our true self is so great that often in many cases people would rather die than to get rid of the false self, because the true self is that precious. And this is true. So, it’s important to understand that something very deep is going on in the second stage a reconfiguring of self.

So what do you do during that time?

Well, the greatest thing that you can do is to nurture yourself, to take care of yourself. In the early stages of this second part, the early parts of the second stage, you may really want just a lot of time to yourself.

I know that in my intensives, often after people do the work of recognizing and acknowledging their Core Gifts, they say, I don’t want to go out there and date right away. I need time to feed myself. I need time to feed these new parts of myself. And so to the degree that you need that, honor it.

But also start looking for the new shoots

Because the seeds of your new self have started underground, but they’re pushing their way forward and upward, even if you don’t see them. So start looking for the new shoots –and that means new things that nourish you deeply. Expression of your creative self, helping other people, doing the things that you have been dying to do for a long time, but maybe you don’t let yourself do. And also new shoots of relationships that are healing and nurturing–start looking now because they will start popping up. New relationships with people who are safe, and honoring of who you are; where your heart and your soul feel safe and seen.

Little by little they start to pop up, and often, you won’t even notice them at first. I find that in my role as a psychotherapist and a coach, often in this stage I point out, hey, what about that really nice person that you just met and you both had a great conversation? And people will say Yeah, I didn’t think of that, that’s right, that’s right. Well, you know you could go to the movies with that person. You could see them at that event the next time you go to the event and maybe go out for a cup of coffee. We need to look for the new shoots of healthy relationships because they will appear in this stage.

Beyond edgy relationships

Now, sometimes they don’t look quite as sexy, and they don’t look quite as hot as those kind of like really edgy relationships with people that dump us and then pick us up again. These bad boys and bad girls. But just because they don’t look as initially as kind of juicy and exciting, there’s a different kind of excitement that we develop a new taste for. This excitement comes from someone’s intelligence, insight, creativity, or ferocity in living a really full life. They may not look as sexy right away, but look for the kind of deeper excitements. Or maybe sometimes people feel like, well you know, I’m just afraid to dip my toes in these news relationships. I see them, but I’m afraid to dip my toes into them. And then we need to give ourselves time and space.

Is trauma holding you back?

Now, another thing here: This may be a stage where trauma is holding you back. This is a really good time to work on that. If addictions or compulsive behaviors are holding you back, this is the time to do that work.

As this stage moves forward, you’re going to develop an itch to get out there and start living and having more fun. And fun is a key. Allowing yourself fun with these healthy new relationships is the way to go. Sometimes I think that people feel in the later parts of the second stage like a teenager who has grown up in a small town and is just dying to get out there and start living. And the way to do that is to look for the new shoots of healthy connections, start building them, start having fun with them, and know that you are actually reconfiguring a whole way of living. That’s part of why it’s taking so long.


Stage 3 – Building A Life That’s Rich With Love



The third stage is the stage where you are actively building a life that’s rich with healthy love. And I know that many of you have done so much of that building already, but maybe haven’t yet done it as fully as you like, in the arena of romantic love. Maybe you have, and you’ve lost your partner. Maybe you’re widowed. Maybe in certain arenas of your life, you’ve lived these lessons, and in others you haven’t yet.

But this third stage is a wonderful stage

It’s the building of the world that you want and, when you’ve gone through stages one and two and you live in a way where you are kind of leading with your soul, dignifying who you are, and having that happen mutually little by little with other people, that’s the foundation of a happy life. That’s X marks the spot for joyful, rich and good life.

In this third stage, life is more full but less full of drama

There’s a kind of peace in this stage, because the people you’re with have a lot less of the quality of psychic violence than maybe people have had in the past. In this stage, in the third stage, our task–now that we know how to suss out healthy relationships and healthy love and relationships and situations that feed our deepest soul– is to begin to look for those people who are safe, and little by little we practice one of the greatest lessons of love that there is.

And that is this: with people who are safe, learning to swing out in terms of how much you give and how deeply you receive. That’s one of the richest lessons of love that there is.

And sometimes this third stage takes different detours

We have to follow where love is calling us. It may not leave right to a relationship, it may lead to something else.

Just to share my story, going on this journey and moving through stage two, I lived through this empty kind of period I’m describing. I created a box and I wrote on top of the box: I can do whatever I want.

And I just kept putting ideas into it, and none of them excited me enough. None of them were right. Until I saw Almodovar’s movie “All About My Mother”, and I stepped out of that movie, and I knew that something had shifted inside of me and I didn’t know what it was. I just took a few minutes to think about what was happening inside of me.

And I realized that I wanted to become a dad

I was a single guy, not making a ton of money, and this seemed like a crazy idea, but my soul was touched by this concept and I chose to act on it. I became a dad. I spent the next big period of time going through the process of adopting my son. And, in the rich new life I had as a dad, my best friend said to me, that’s where I think you can meet your partner: an event for gay parents. And that was true, that was where I met my husband. That was a number of years down the road, but I followed the call of love. And in this third stage, we follow the call of love, including with romantic intimacy.

When you’ve reached this stage the field will have changed for you. The people you notice will be different. It’s amazing that it’s true, but it is true, because your attractions will have changed.

So this is now where you start looking for your joyful life. You will be meeting people who are kinder, who are more available. Your dating life will change, in this phase. And there’s more work to be done when that happens.

For example, those of us who are used to unhealthy relationships, when we finally meet and start having deeper feelings for somebody who’s really kind, really decent, and really available, we will often start getting afraid. We’ll want to push them away.

The wave of distancing

And there’s a process that needs to happen with how to handle that. I call this the Wave of Distancing, and we’ll talk about that in a future podcast–how to handle that. But what can happen is that you’re going to need to learn in this phase a whole new set of deeper, richer communication skills. We’ll be talking about that a lot more. But the heart and soul of this third stage, is cultivating and deepening your connection with those people and those situations that nurture your soul in a safe way. That is the journey of this phase. And it’s truly, truly, the journey of happiness.

So take a minute to think about where you see yourself in this journey

What stages of deeper dating are you occupying? Now, you might be occupying a few different stages at once. You probably, though, are primarily in one of the stages. Think about where you are and what your steps are to move ahead forward in this journey. And this journey is the richest journey of love. This is the journey of populating your life with love and building your life on a foundation of love. And it’s the greatest path to joy that exists.

Now, are there only three stages of deeper dating, and does it end with stage three? Of course not. There are constant learnings. There’s constant growth that we need to do. It is a continuing and ongoing and incredibly humbling and complex process, again and again and again. But these grand and broad stages are stages that hold true, and if you have cultivated these healthy relationships, and you’re cultivating the tools to help them flourish, then you are on the right path and you are on the path to happiness.

So, I’d like you to just take a minute

Think about what you’ve learned in this podcast. Think about the thing that stood out the most for you about what your next steps are, right now. Maybe it’s saying no to some unhealthy relationships. Maybe it’s doing things that nurture yourself. Maybe it’s calling someone who–now you think of this–is one of your tribe, kind of this new generation of healthy relationships. Maybe it’s making plans to do something that’s really fun and really nourishing with a good person. Just take a minute and think about a next step for you.

And I encourage you to take that step. As you’ve followed this path, you will experience again and again that wonderful place where peace meets joy, where there’s an inner peace and a sense of goodness and safety, and it meets a sense of fun and joy. And that’s really what life is all about. But it can’t happen until we take these steps.

So I wish you blessings, excitement, adventure and fun wherever you are in these stages, and in the stages that you will follow in the future.


Discover more about the three stages of deeper dating in Ken's book
Discover more about the three stages of deeper dating in Ken’s book