Deeper Dating Q&A: Expert Advice For All Your Questions About Love, Dating And Sex [EP114]

In this Deeper Dating Q&A episode, listeners bring their most important questions about love, sex, dating, and relationships to Ken and get his direct personal advice. Today, we’ll talk about what to do when someone you’re dating starts to pull away; deciding to become a single parent, the single most powerful way to change unhelpful dating patterns, and much more!

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Deeper Dating Q&A: Expert Advice For All Your Questions About Love, Dating And Sex

Welcome to the Deeper Dating Q&A, where I answer your most personal questions about love and sex and intimacy, in a way so that listeners can apply these insights to the particulars of their own intimacy journey, and leave the episode with new possibilities and hopefully, some really important revelations about their own love life, so stay tuned to the Deeper Dating Podcast.

Hello and welcome to the Deeper Dating Podcast. I’m Ken Page and I’m a psychotherapist. I’m the author of the book Deeper Dating and the Co-founder of, a site where single people can meet in an online environment that is kind and respectful and fun and inspiring. In this episode, I’m going to be answering your questions. There are some really amazing questions that I’m excited about getting to and sharing and reflecting on. In every episode, I’m going to share with you 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 nothing more than the deep skills of intimacy, which are the most important skills of all for the kind of rich life that we all want to have.

If you want to learn more about deeper dating, just go to You can sign up for my mailing list, get free gifts, a lot of resources, and learn more about how to use these ideas to transform your intimacy journey, and you’ll also find a complete transcript of every episode. Just a couple of more things, I want to say that everything I share in this podcast is educational in nature. It’s not medical or psychiatric advice or treatment. If you feel like you need help, please do seek professional help. You deserve that. Finally, if you like what you learn, please do feel free to subscribe and leave me a review. I always appreciate that really deeply. There are just such amazing reviews and I so appreciate that. Okay, let’s jump in.

Someone called in with a really poignant question about becoming a parent as a single person. I’m very excited about responding to that. That’s one that is really very personally relevant to me, and I can share my experience, and I’m excited to share some thoughts. This person said some really kind things about Deeper Dating and acknowledged how, for the first time, she was able to end a relationship that was not healthy. She had not ever been able to do that on her own before, so she’s very thankful for that.

Sometimes when we end a relationship, when we take a step that really gives us freedom and mastery and empowerment, a new door opens up. That happens so often. It’s like the deeper physics of dating. This happened for her but in a different way. The way that it happened for her was that she’s 39 years old, and she had a revelation of how much she wanted to have a child. That happened to me when I was 45 years old, 44 years old into 45.

DDP 114 | Dating Questions
Dating Questions: Happiness is when you see how the person you love looks into your eyes and feel the love there.


This was her revelation. She had never considered having a child by herself, and a friend said something to her that just profoundly influenced her. Her friend said, “You’ve always thought about having a kid like that’s when your life stops, that your freedom stops, that your life stops because you have to focus everything on the kid.” She said her friend said though, “What if your life has stopped because what you really want is to have a child, and you have blocked that and not admitted it? What if your life has stopped because you’ve blocked this deep and profound longing to have a child?”

This hit her so deeply and she had an experience of uncontrollable tears. The tears just poured out in a flood, and she’s wondering about this now. She asked, “Was it scary for me to adopt a child as a single parent to take that journey myself, and how did it influence my ability to find a relationship?” I’m going to say something about that but first, I just want to talk about the power and the beauty of that experience. I want to ask listeners, have you ever had an experience where someone said something to you that released a flood of healing tears? Just take a minute. You can even pause this and think about it because those moments are so precious and so important.

I remember when I was on my journey, I had a number of times like that. Once, seeing a mom with her little baby. I went into another room and all of a sudden, I was just brought to my knees in tears with the desire to have a child, and the kind of admitting of how much I wanted that. Another thing I want to say about this is it’s just there’s something so profound in this that’s a really universal thing, which is that when we have a deep truth about who we are and what we want, and we don’t live it, it is not just suppression. It is an act of quiet violence against our being. It always ends us up, this is that deeper physics thing, in a situation or situations that are somewhat masochistic, where we live a deeply reduced experience of who we are.

Understanding Your Truth

I was speaking with someone recently who had been through college and left, and didn’t have a good experience. They had this revelation which was, “I was not my true gender identity,” which is gender-fluid, non-binary. “I was not that me, so I couldn’t appreciate or live in the college experience because I was denying who I was.” This woman had a deeply rich experience of her truth which is that she so wanted a child. That was her truth. Here’s what I want to say about that. I understand that journey. Having a child is not for everyone, but if you do have that deep longing or, listeners, any deep longing that is so deep, that it actually feels like it’s your identity, or can lead you to these kinds of revelation experiences of emotion just flooding out when you recognize something. If you don’t pursue it, you limit yourself.

If you don’t pursue your dream, you are limiting yourself.CLICK TO TWEETI remember somebody saying something really wise to me when I was going on that journey. I just want to say this is not just about having kids. These ideas apply to your mission and your passion, and it might be to have a relationship. It could be anything. It might be to really embrace the fact that you’re an artist or you want to write a book or whatever it is. The stoppage that happens isn’t just the stoppage of that particular impulse. It’s a stoppage of the flow of your being, which has profound repercussions.

I was talking to somebody about my own desire to have a child and my fear. I said, “I’m a psychotherapist. I don’t make a ton of money. I don’t have the savings that can allow me the freedom to just get an au pair and not worry about this, and I’m single, and I’m single. How am I going to do this? How am I going to date? How am I going to have a life?” She said something so beautiful and wise to me. She said, “You’re evaluating your life now and imagining what it would be like having a child in your life now, but when you make this commitment to have a child, the circle of your experience will widen and broaden.”

She said that there’s a German saying which is, “A child brings its own luck,” but she said, “What that means is that the circle of your luck is going to expand,” and God knows it did, and that’s how I found my wonderful husband and now my other two children. It was through pursuing that deep longing and impulse. This is where I get to say to all of you, what’s yours? What’s your deep longing? What have been those moments that you got kind of like hit with a longing that almost felt torrential or powerful or profound? Maybe not like that, but just in some simple and steady way really identifies who you are.

That is your soul and you will widen the circle of your luck by embracing that, because you’ll widen the love in your life because you’ll be living love, and in this case, love of self and love of your mission, so that’s this kind of esoteric truth, is that when we block the flow of that, we crimp our being. We diminish our being. It’s an act of quiet violence against our being, and violence begets violence. In this case, what that means is that if we reduce ourselves by not pursuing our dream, somehow we will encounter situations again and again that conspire to reduce us. As Jung said, “It’s going to feel like fate, but what it really is, is the shadow of the dreams that we are not embracing.”

Not Wanting To Be More Than Friends

Okay, so moving on next. Someone else spoke about being in her 60s and dating. What she finds is that guys keep just wanting to be friends. Again and again, the guys that she goes out with, she kind of stays in a friend zone with them because she senses that that is what they want, that they only want to be friends. She was speaking about one guy that she had gone out with for a really long time, and is still connected to that has landed kind of solidly in that friend zone, and she had a revelation. She realized that she didn’t have the courage to tell him that she was interested in exploring something deep. She said it just made her feel so vulnerable. She acknowledged that she just didn’t feel like she had the courage to do it.

DDP 114 | Dating Questions
Dating Questions: When we have a deep truth about who we are and what we want, and we ignore it, it is not just suppression but also an act of quiet violence against our being.


I want to zoom out for a minute and kind of look at the bigger picture here, and then zoom in and share some specific thoughts for her, but zooming out…..I think that one of the great harms, profound harms that’s done by treating the search for love as almost more like a gimmick or a series of hacks or tricks, or focusing on just making yourself more attractive, etc., the not treating it as a deep and profound growth journey, is that we miss the biggest points. One of the absolutely hugest points is that we need to become a student of our patterns.

That’s how we can mark if we’re growing and progressing because we notice that we’re approaching different people. We’re becoming attracted to different people. We’re avoiding different people, that all of those things are changing, that somehow we’re meeting people who are kind of closer to what we’re looking for, closer to what I call attractions of inspiration versus attractions of deprivation. When we see that, even if we haven’t found our one yet, that is cause for such profound hope.

Cherishing Your Core Gifts

That’s the second stage of the deeper dating journey. The first stage is the discovery and naming and cherishing of your Core Gifts. The second is the re-education of your attractions because we cannot force our sexual attractions, and we should not try to. However, we can educate over time our sexual and romantic attractions, and the tools for doing that are the tools that are going to help you keep sex and love and romance alive when you find your beloved, but that’s for another episode and another discussion.

The kind of first layer of experience that she has had has been the layer of experience of, “This keeps happening to me.” We all have like a lot of stories as we get older especially of, “This keeps happening to me.” Although I know 18-year-olds and 19-year-olds and 20-year-olds who totally can tell the “This is what keeps happening to me” story, but we need to stop and examine that. What is it that keeps happening for you? Because whatever that is, there’s so much to be learned from that. Not just what to stay away from, but also if anything keeps happening again and again, it’s a deeper and richer statement about the parts of ourselves that we have not learned to honor, dignify and have wiser custody over.

We need to become a student of our patterns.CLICK TO TWEETThe two link, the places where we don’t love ourselves, are connected in very rich and sometimes complex, sometimes simple ways. They’re the kind of people that we’re sexually and romantically attracted to. This is a rich and amazing thing that all of us should learn to understand. In my book, in my courses, and all of my work, I teach that in really clear structured ways, which is something I’m very passionate about. Anyway, so she reached the point where she had this first story of, “This always is what keeps happening to me, which is guys keep just wanting to be my friend,” but then in reflecting in a deeper way, she realizes that there’s something deeper here, which is that she is afraid of sharing the part of herself that wants to depend, that wants to need, that wants to lean in, that wants to be held, that wants to say yes to a deeper, committed relationship, and this is gold.

When we can see how we’re afraid of intimacy and playing that out, we have gold. That’s where we need to get help. That’s where we need to get support, at exactly that juncture, because that juncture is gold. It might knock us to our knees that saying that the truth will set you free but first, it will make you miserable. Yeah, that’s true but she’s got it. She’s got it and what that is, is that she is not having the courage to own her deep longing for intimacy and connectedness which is her treasure. This is your treasure, so what do you do about it? First, you validate yourself for seeing it.

I want to ask every listener here to take a minute now. What is your “This always happens to me” kind of story? You know the truth of that piece of it. What might be the deeper truth of what you are afraid to reveal or honor or cherish? You might not have an answer yet. Another way to ask that question is, “What does your wiser self have to say to you about what you are not doing in your search for love? Is there any piece of wisdom, something your friends have told you, something you know that you’re kind of preferring to avoid, but you know it’s like really a big deal and really important?

I had a friend who said to me once. I’ve talked about this before, but she said to me after my being single for like decades and decades, and really upset about it and wanting a partner. She said, “Ken, I know why you don’t have a partner and you kind of know why too.” I said, “Please educate me because no, I don’t.” She said, “You’re always going to the bars. You’re always going to the clubs. You’re going to look for people in those environments, but not in places with people who share your values.” I proceeded to ignore that with great passion for about 8 to 10 more years, and then finally, kind of was brought to my knees and said, “Yeah, that’s true and that’s what I need to do.”

Anyway, what I want to say to you, you’re feeling like you don’t have the courage. When we feel like we don’t have the courage for something, there is a simple response to that. We do the internal processes to build courage. Yes, but we don’t bank on those. We don’t count on those. We almost give up on those, trying to pull ourselves up by our bootstraps, and we look for connection and support. I promise you, you will be able to take that next step infinitely better if you have friends or a coach or a therapist or a group or a combination thereof of people who can support you in this terrifying experience of saying, “This is who I really am, and this is what I want.”

DDP 114 | Dating Questions
Dating Questions: One of the great harms in the search for love is focusing on making yourself more attractive and not treating it as a profound growth journey.


The liberation that you will experience with that will not only impact your relationship with this person, it will impact your life because like the last piece I talked about, that holding back of who you are, which is this precious quality of longing for a deeper connection. When you hold that back, you hold you back, and everything there gets crimped and stuck and blocked as a result. Terrifying? Yes. Thrilling? Absolutely. Don’t try to do it alone. I want to say this to each one of you as well. If there’s a pattern that you want to change or break, don’t try to do it alone because your life will not expand in the way that it needs to. It is an incredible truth how interdependent we are.

It is wiser to give up on trying to pull yourself up by your bootstraps. It is truly wiser and get help because time is precious, and I can pretty much promise you that you will speed your journey so much more beautifully with the proper support. Everybody who is listening, take a moment to just think about where that might apply to you in your precious, precious life and intimacy journey. For the next few Q&As, I’m going to go a lot, lot quicker because I’m kind of backed up in the Q&As, but please keep sending them to me. I love them. I adore them and I get to them little by little. The next ones, I’m going to do are a little bit quicker.

Someone called into the Ask Ken section of my Deeper Dating Podcast website, which is how you can leave your questions. I had a number of people that responded after my podcast episode about chemistry. She said that there was a guy that she went out with, and they had good sex. They had a beautiful connection. He was a lovely guy but she ultimately, in that process of dating, went back to someone who was a toxic, intense rollercoaster relationship. She was heartbroken for that person, and she ended this relationship, then she listened to my chemistry podcast and she asked me, “If I look at this guy with new eyes, is there a chance that I could fall in love with him?”

I want to respond to that. Those white-hot, crazy attractions of deprivation grab us, and they grab us in a really vulnerable place. They grab us in all the places where we feel like we’re not worthy of being loved. We finally are almost getting loved by someone who also can see the ways that we’re not worthy of being loved, but will choose to love us anyway. That’s the construct, and that’s the unbelievable excitement of these people. Our psyche wants to go back to the scene of the original crimes and finally be loved right.

Don’t pressure yourself romantically. Give yourself space, and enjoy the person that you are.CLICK TO TWEETIt’s white-hot. It’s intense, but what it doesn’t have is that place of deep peace. I say this all the time, and I’ll say it again. When you have that feeling of deep peace because of someone’s goodness and integrity, and they’re hot and they’re sexy, and they love you and they’re there, and when you see how they look into your eyes, you see the love there, that’s happiness. That’s where you want to build your home, and that exists. Those are attractions of inspiration.

What I would say to you is there is absolutely a chance that you could fall in love. If it’s not too late, get to know this person. Follow the ideas that I talk about in the chemistry podcast which are don’t pressure yourself sexually, don’t pressure yourself romantically, give yourself space, enjoy the person, kind of let yourself fetishize the personality and sexual and physical things that you like about them. Let yourself taste those, reflect on them. Let yourself fantasize about sex with this person. Let yourself fantasize about enjoyable times with this person. Use these tools to grow Eros, which is what you’re going to do in a long-term relationship anyway. It’s fun and it’s a beautiful thing to do, and it’s a tool that we all need, so do that.

Extra Spark

So often, your focus, get to know this guy if it’s still a possibility, but here’s what I would say. Who knows if that like kind of extra spark that you felt was missing will come? If it doesn’t come, you will know. If it comes and goes, then you know that this is worth pursuing and exploring. What happens when it comes? What happens when it goes? If it comes in a strong way, which it really might, that’s a glorious thing.

Mirror Image

Okay, I’m trying to move a little more quickly so I’m going to move to the next one now, which is just kind of so fascinating. It’s the mirror image. It’s someone who also has spoken about how much she has kind of loved this content, and how it has helped her and changed her. She said, “I was with someone who saw me as what I call an attraction of inspiration, but he went back to a toxic rollercoaster relationship.” She suspects that it’s the wave of distancing, which is when someone is available and decent and kind, and all of a sudden, we lose interest in them, and we kind of start devaluing them in our head, or all of a sudden, we start remembering this hot, unhealthy relationship, and we want to go back there. This is such a deep human tendency that we have not been instructed about. She said she feels compelled to share what she has learned from Deeper Dating, this concept of the wave, which I think is the single biggest saboteur of healthy, new love.

She wondered, “Should I speak to this guy? Should I tell him what I’ve learned?” I would say, “Sure.” You can kind of offer one of my Psychology Today articles, the podcast episode, or any of those things where I talked about the wave and say, “I just wonder what you think about this, and might this have been something that has been true for us?” That’s really all you can do. If there’s continued dialogue, then that’s great, but you can certainly offer that. I just feel like, absolutely, why not, but realize that this person is in the throes of an avoidance of intimacy, quite possibly, and also quite possibly, a romantic obsession, and those are powerful things like any addiction that we don’t have as much control over as we’d like to, but I say, “Sure, why not plant the seed?”

DDP 114 | Dating Questions
Dating Questions: Sometimes, when we end a relationship, a new door opens up possibilities, and we take a step that gives us freedom, mastery, and empowerment.


The last question for today is somebody who thanked me also for this work and said that his main learning has been a deeper learning to love himself, but here is his question. The concept of attractions of deprivation and inspiration, you can find those in earlier episodes. I talk about two circuitries of attraction, Attractions of Inspiration, where attraction and Eros grows because of a person’s goodness, availability, integrity, love and caring for us, combined with the fact that they have to be sexy and attractive to us, or an Attraction of Deprivation, which is where we kind of are chasing love.

What he asked me was, “Can there be elements of deprivation in an attraction of inspiration?” To which I say, “Absolutely, 100% yes.” This is so infinitely not black and white. We’re human and we’re all filled with holes and gaps and triggers and traumas, but the question is, “Is something essentially so? Is someone committed to curating a life where they are essentially decent and honest and integrity-based? Do they have an unstabilized serious psychiatric condition that they’re not working on? Do they have an active, serious addiction?”

These are all things that can help you decide if, overall, this is something that is safe to pursue, but within that, Harville Hendrix says this really beautifully. He says, “We come to a point in our intimate relationship, often, years in, where the thing we most need from our partner is the thing that they’re least able to give us, and that’s not the end of love. That’s the beginning of conscious, deeper love because you build bridges together, and you work on that together,” so absolutely, but the question is, “Over time, is there an essential, basic sense of trust in the person’s goodness and integrity and availability and decency, and all of those basic, basic things?”

If that is there, then you work on that other stuff. That’s hard and difficult and ongoing and stressful, and also wonderful, but that’s the work. The thing is you want somebody who is able and willing to do that work with you, and cares and is committed enough to do it, so that’s my kind of answer on that. Thank you all for listening. I look forward to connecting with you on the next episode of the Deeper Dating Podcast. You might even just want to take a minute now and just ask yourself, what touched you most in this? What’s a message in this episode that touches you and matters and that you want to carry forward in your own life? Thank you all so much. Have a great day.

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