5 Questions That Will Illuminate Your Path To Love [EP081]

These 5 questions truly will illuminate your path to love. Just answer them as you go (no need to write anything down), and by the end of the episode, you will understand some of the most profound truths of your life journey and your search for love. In the words of Chip Conley, “A question, thoughtfully conceived, can illuminate a room, a company, a life.” Let’s do this together!

Table of Contents

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5 Questions That Will Illuminate Your Path To Love

Answer Them As You Listen, And Watch The Shifts Happen Inside

Chip Conley, a brilliant business person and the Founder of the Modern Elder Academy says, “A question thoughtfully conceived can illuminate a room, a company, a life.” Today, I’m going to ask you a few questions that will illuminate your intimacy journey and your search for love. Stay tuned to the Deeper Dating Podcast.

Welcome to the Deeper Dating Podcast. I’m Ken Page. I’m a psychotherapist, the author of the book, Deeper Dating, and of course, the host of this show. I’m happy to have you here today. I’m going to be talking about five questions that will illuminate your search for love in some quite amazing ways. This week and every week, I share with you the greatest tools and insights I know to help you find love, keep it flourishing, and heal your life in the process because the skills of dating are nothing more than the skills of love.

If you want to learn more about the deeper dating path to real intimacy, just go to

DeeperDatingPodcast.com. If you sign up for my mailing list, you’ll get free gifts and learn more about how to use these ideas to transform your own intimacy journey and you’ll find transcripts of every episode there as well. I also want to say that I am now launching something that you can go to DeeperDating.com to find out about it and what it is, is a whole new way for single people to meet online, in a way that is warm, inspiring, emotionally safe and fun. We’re just beginning, but if you want to go to DeeperDating.com to learn more, we would love to have you be part of this wonderful experiment in a wiser, more inspiring online dating. I also just want to say that everything I share in this podcast is educational in nature. It’s not medical, psychiatric advice or treatment. Finally, I just want to say, if you like what you’re learning here, it would be wonderful if you could subscribe and leave me a review. Thank you so much for that.

In this episode, I’m going to ask you five questions. These are questions that are built to help you understand the richest, deepest, most essential themes in your entire intimacy journey and your search for love. With that also, the richest deepest themes in terms of your own journey to selflove and self-understanding. Those are big claims, but you will see as we continue why these claims are very real and very true. What I want to encourage you to do is answer the questions as we go. Whether you’re driving, running, or just sitting down, I would encourage you not to wait because they’re deep questions and you just want to enter into this. We will take you into it deeply, bring you out the other side, and you’ll have pretty glorious insights along the way. Maybe you’re that kind of really organized person that you could say, “I’m going to come back to this and do it later.” I know I’m not that person. My suggestion is not to make a fuss about it, but just jump right in, answer the questions as you go. I’m going to answer some for myself too as an example, and then later, if you want to do it in deeper ways, feel free to do that. One other thing that I just want to say is that part of the questions I’m going to ask are pretty profound. They’re going to be about parts of you that you thought you had to hide, which you are now learning to instead embrace on your intimacy journey.

Answer these 5 questions to understand your entire search for love in a new way.CLICK TO TWEETFor some of us though, that entails trauma, and I want to encourage all of you, if you feel these questions could activate trauma responses that are hard to deal with and hard to bear, do this with a therapist or someone who you trust to be able to help you get through this and get to the other side. This is for people who’ve experienced trauma and might have PTSD symptoms around questions like that because we have to honor our places of trauma and we have to protect ourselves and be kind to ourselves. If you’re not sure, you can go along with the process. If you hit a question that just feels like too much, don’t answer it until you can get the support that you need. Let’s jump into these really fabulous questions.

What Is A Part Of You That You Thought You Had To Hide To Make It Through Your Childhood?

We’re, this is going to be very much starting with is when you were younger. We’re going to be doing sets of these illumination questions a lot in the future on this podcast, but now we’re going to start with some childhood stuff and then move it into the present. Here’s a question, “What is a part of you that you thought or felt or believed you had to hide in order to make it through your childhood?” I’ll just give you some examples. For me, there was a quality of intense sensitivity and vulnerability that was like way too gay and mortifying for me, and also not fitting in with what a boy was supposed to be, not fitting in with what a boy was supposed to be in my family of Holocaust survivors and our family ethos about what it meant to be tough in order to survive. This deep sensitivity in me that was explosively loving and extremely tender and very magical was something I had to really protect and hide. I grew a kind of shame around it for myself. That’s me.

For you, it might have been a quality of power or fierceness or independence. Maybe a quality of sensitivity. Maybe a creativity that was like wild and careening that got you in trouble, but whatever it was, this kind of like a very essential part of you as a kid that you knew the world was not going to see or get or honor. Take a minute to think about that. You can say your answer out loud if you’re all alone, just do that. Take a minute. You can pause the recording right now and just say your answer or you might want to write it, or you might just want to think it. Again, I encourage you just go for it because you’re going to learn some great things unless it feels too emotionally loaded to be doing right now and then I encourage you to respect that. Do that right now.

Who Gave You A Sense Of Hope That There Could Be A Place For This Part Of You To Be Honored, Safe, And Appreciated?

Here’s the second question, “Who in your childhood gave you a sense of hope that maybe there could be a place for this part of you in the world? Maybe this part of you could be honored, could be safe, could be appreciated, could be mentored, could be empowered?”. Who in your childhood gave you that glimpse, even if they weren’t intensely in your life? Edward Hallowell, who’s just a hero of mine and a brilliant thinker about ADHD, about intimacy. I’ve interviewed him before and I hope to again. He spoke about having a really difficult childhood, but there was one teacher who saw his gifts, and he said, “You know, even just one teacher can be enough to bring somebody into a really rich and good life, even if they didn’t get that from their family of origin.”

Maybe it was an imaginary person. Maybe it was someone from history. Maybe it was a saint. Maybe it was someone you invented. Maybe it was a pet. Maybe there was no one though from your childhood that you had that with, but you had it later in your life, but someone with whom this part of you, they got it. You felt like, “This part of me has value. It can be seen. It can live in the world.” Take a minute now and think about who that person is. I’m going to ask you again to pause the recording. You’re going to think who this person is, and then you’re going to do something. It’s something I do a lot. It’s an important part of this illuminating your path process. You’re going to thank this person. You’re going to put words on what it is that they gave you.

DDP 81 | Path To Love
Path To Love: There are parts of you that you think you have to hide, but you have to learn to embrace them on your intimacy journey.


For me, it was a woman named Naomi Sheldon. I was twelve years old. I went to my violin class and she was sitting there. She was older. She was like in her twenties and she had a singing class. She was a poet and she met me and she got that I was a sensitive kid with a big heart. She remembered all the pain that she had been through being that kind of person, but something that she said that intrigued her about me was that I seemed like a pretty happy kid, which may be on some level I was. She wrote a poem about me. We became friends and she became a mentor. She brought me to the theater. She taught me that I could live as an artist.

No one had taught that to me before in that way. Even though I came from an art family, but that I could live like an artist. In other words, feeling things that were so deep and so wide and so explosive and so tender that there was space for that and that it was actually a gift. That was me, but I would like you to think who this person is. I’d like you to pause the recording. I would actually like you, out loud or silently, to put words on your gratitude to this person.

Tell them what they did for you, how it changed you, and also talk about the part of you that they rescued or allowed and the role that they played. Just take a minute or two to do that or three and then you can start the recording again. Just give yourself that gift because when we know these people who saw what I call our core gifts and let us know that there might be a place for them in the world, that’s really big. That’s really seminal for our life journey. I’m going to talk about why with the next question. Go ahead and do that now.

How does that feel? I bet it feels good. It’s a really important thing to do. These intimacy heroes, these core gift heroes in our life. Here’s another thing. I am a student of intimacy walls because I have had so many intimacy walls and still experience my intimacy walls. They really mattered to me because of the loss of love that they cause, which really I feel. I’ve had to do tons of thinking for my own life and then as a therapist and in my intensives, intimacy walls are what I work with. Those are the places where we feel like they’re impenetrable, they’re impermeable. The thing that I want to say and this is a rich formula, whatever it is, that quality was, that you picked out to the degree that you feel like it won’t be cherished, you will put up walls.

These walls will be what they call primitive defenses, meaning that they’re frozen, they’re automatic. It’s like a deep down part of ourselves that does it to protect us. The more we treasure these parts of ourselves, the more we’re brave enough to live them in the world more freely, of course, appropriately, and in ways that are safe because it can be a scary world. The more that we inside ourselves have rid ourselves of shame and celebrate these wild, sensitive, passionate parts of ourselves, the more we do that, the less we will need primitive walls against love. The more shame we have over these parts of ourselves, the more we will erect walls against love that we won’t have control over.

The more we rid ourselves of shame and celebrate our wild, sensitive, passionate parts, the less we need walls against love.CLICK TO TWEET

“How Do You Put Up Walls To Protect This Part Of Yourself?”

That’s a question that I want to ask now and this is first iteration. Maybe you’ve thought about this a lot before but if not, don’t worry about it. This is first iteration. You’ll be thinking about this a lot more, I imagine, afterwards. You can see that these questions illumine your whole life story in a way. How would you put up walls to protect this part of you? When you were younger, when you were older, when you date, how would you in the past, how do you even maybe now put up walls to protect this part of yourself? Because it’s smart to protect this part of yourself.

The more you learn how to dignify it and champion it and honor it, and be amazing enough to stand behind it, even when the world doesn’t get it, the less you will need walls, until then we need walls. As we grow, the conscious journey is to deconstruct the primitive walls and create and rewire new ways of behaving that honor and treasure these beautiful parts of ourselves, and then only choose people and situations where these parts of ourselves can grow and flourish and shine. Take a minute to think about this one. How do you put up walls to protect this part of you? You can pause the recording and just kind of speak it out again.

Who In Your Life Today Sees These Parts Of You That Allows You To Feel Safe, Treasured, And Cherished?

I know this is a deep one, folks. Next question. This is a wonderful question. Who in your life today sees these parts of you, allows you to feel safe revealing these parts of you, treasures and cherishes these parts of you, respects these parts of you? I want you to just think of those people and I want you to thank them. We’re going to do the same thing again. You can just pause the recording and speak it out loud or write it or think it. I want you to just think of some of those people. If there is no one like that, I have two suggestions for you. The first suggestion is when we’re not used to people like that, we sometimes don’t recognize or notice them. They’re like invisible because they’re so different from what we picture life is really like so we don’t recognize it.

I’d like you to think in your Facebook friends, in whatever kind of contact list you have, I know for me, this was a really big and important question. I had to look back through my current and past life to find out who were the people with whom these parts of me felt safe because I had to develop a taste for those people because for me, I thought they weren’t spicy enough. I thought that they weren’t exciting enough. There was an excitement wiring that happened to me around people that didn’t really accept me. It’s a deep internalization of the people who stepped on these parts of me and the parts of me that believed that they were right to do that.

I had to relearn like, “Who are these people?” Maybe they didn’t seem so spicy at first, but maybe I would find that their edge came from their intelligence, or their fierceness in living, or their deep integrity. There were other kinds of edges or their radical gentleness, even when it’s hard to be gentle. There were other things that could be really exciting and spicy for me and I could learn to develop a taste for those people. I’m just sharing my story because when I finally did that, that my world became filled with love.

DDP 81 | Path To Love
Path To Love: The more shame we have over some parts of ourselves, the more we will erect walls against love that we won’t have control over.


Take a minute now and think who were the people, just think of 1 or 2 people who really stand out for you, just at this moment and thank them, articulate what they give you with this and thank them and just do that. I mean, you’ll love this because it feels so good to do this. If you’re someone who still says, even after reflecting back on other people, you might not have noticed that there’s no one, then your work is in front of you because I promise you that those people are there and that they are your path to happiness. Your work is to find them and you might need help and support to do that. Take a minute now, press pause and go ahead and enjoy that.

How Could You Allow This Part Of You More Of Its Genius In The World?

Now, we are on our fifth and last question, and the question is this. “How could you allow this part of you more of its genius in the world? How can you allow this part of you more dignity in the way that you live? More leadership because this part, I believe, is connected to your mission and to your greatness and to your capacity for magic in this world. The messages that come from this part of you are messages that the world is hungry to hear, or at least parts of the world are hungry to hear.

Their messages and ways of being that when you find your one, that person is going to feel like they found home because of these very parts of you. Take a minute and just think, “How could I let the genius of this part come out more? How can I treasure this kid inside me more? How can I give this wild, kind of very unique, very different, very challenging, but very amazing child inside of me freedom to really create and to be and to live in a bigger, richer way?” Take a minute and pause and just put words on that.

Those were your questions and I imagine that they’re going to be questions that are going to ripple and bang around and rock around and just touch you and affect you and affect your thinking and help you understand your path or one aspect of your path and your journey just a

little bit more richly. It was a joy to get to do this with you. I want to encourage you to go to DeeperDatingPodcast.com and click on Ask Ken, and you can leave a message about what this exercise brought up for you or what you learned from it. I always love hearing that. Some of those, I might read out actually in the podcast. Thank you so much and I look forward to seeing you on the next episode of the Deeper Dating Podcast.