Today, as we mark the end of Pride Month, I want to share my own story. It is a story of sex, hooking up, and love. I hope you will take away some lessons that you can apply to your own life and the search for love. In this episode, I talk about my own journey of self-love and the process of becoming a student of what I was doing wrong in my search for love as a gay man living in New York City in the 1970s. I also share the steps along my journey to happiness and break down the deeper physics of dating.

Listen in to learn which important questions you should be asking yourself about sex, how to recognize patterns in your love life, and the dangers of hookup culture.

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Show Notes:


  • Important questions to ask about sex
  • How to recognize patterns in your sex life
  • Ways to analyze the pace of your sex
  • What was it like to grow up gay in 1970s New York
  • Dealing with the loneliness of hookup culture
  • Dangers of hookup culture
  • Why it can pay to wait on sex
  • Infatuation red flags
  • Prevalence of trauma surrounding sex
  • Revelations in the gay men’s community


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6 month coaching and mentorship intensive with Ken Page


Sex, Hooking Up, and Love (My Story)


In this episode, I’m going to talk about hooking up and sex and love. And I’m going to share my personal story about all of those things. So stay tuned to this episode of the Deeper Dating podcast. Hello, and welcome to the Deeper Dating podcast. I’m Ken Page, and I’m a psychotherapist, the author of the book Deeper Dating, and the host of this podcast. And today I’m going to be speaking about sex, hookups, intimacy, and gay men, and I’m going to kind of tell my story about these things.

So in this episode, and in every episode, I am committed to sharing the greatest insights and 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, and those are the greatest skills of all. And if you want to learn more about the Deeper Dating® path to real intimacy, just go to You can sign up for my mailing list and receive free gifts and lots of resources. And you’ll also find a complete transcript of this and every other episode. And by the way, if you like what you’re learning here, I would love it if you could subscribe and leave me a review. So thank you so much for that.

So today I want to talk about sex and hooking up and love. And I want to talk about this from a bunch of different perspectives. One, most importantly, I’m going to share a lot about my story. Two, as a psychotherapist and a coach who works with these issues, I’m also going to be speaking about it in that way. And three, as a fellow explorer, I’m just going to share some questions that I think are really rich and illuminating. So my dear friend Chip Conley, who is the founder of the Modern Elder Academy, and just a kind of all-around brilliant person, said that a really good question can illuminate a conversation, a room, a lifetime.


If there was one quality I was most ashamed of it was goodness. Click To Tweet


So, I just want to start with a few questions that I think can illuminate so much around sex. Okay. So what parts of yourself do you skip over-sharing and showing in sex? Do you skip over kind of really revealing and experimenting with and asking for and from in sex? Like what parts of yourself are you shy about revealing in sex? And I love this question and I think all of us can have like really important illuminating answers to each of these questions. So here’s the next question. In sex, what are behavior patterns that you act out again and again because they’re familiar, but maybe not your truest expression? Another rich, rich question.

And here’s another question. What parts of yourself do you joyfully express in sex? So give yourself a minute to think about that fabulous question too. And here’s another. What kind of pacing in sex unlocks your vulnerability? And what kind of pacing shuts you down? What kind of pacing unlocks a sense of wildness and passion? And what’s the sequencing of that? What kind of pacing and pacing shifts in sex allow you to have wildness, passion, safety, and vulnerability?

I just love the thought of starting with these liberating questions as I kind of dive into my story. And I think in some ways reflective of so many of our stories around shame and sex and finding ourselves in sex. So I kind of came up in the gay men’s world of New York City, bathhouses and back rooms and clubs and bars. And I lived in and reveled in and looked for love in those environments for many, many years.

And I was pretty much a complete failure. I mean, I had a lot of sex. I mean a lot, a lot, a lot of sex. Kind of uncountable amounts of sex. And I grew up in a culture where that was what we did. And there’s a kind of forced loneliness that I didn’t recognize I was experiencing that people in my day and age had, I think, and many people still have today that’s very powerful and creates a kind of build-up of need and desire and loneliness and shame. A whole kind of soup of that. So I’m going to go back a little bit now. I remember being a kid, being like 12 years old, and I remember the cloud of shame and sadness and embarrassment and dread that I felt spending so many hours on the floor of the library shelf that had books on homosexuality.


Sex, Hooking Up, and Love (My Story)

How to recognize patterns in your sex life: What parts of yourself do you skip over-sharing and showing in sex?


So I was born in 1956, and so maybe this was like 1967 or 1968. And it was book after book that said that homosexuality was a pathology that would lead to loneliness, a despairing twisted life, and maybe jail. And it came from having a close binding mother and a distant father, both of which I had. So, you know, it fit perfectly that I could think of this as a pathology. And the world’s greatest thinkers on the subject all said the same thing. There were a few more wonderful books that were more positive, but almost all the books and the books that I focused on painted a picture of shame. And shame was injected into me like a dye, like an ink, and formed me in so many ways.

And I remember just sitting on the floor and reading and reading and feeling more and more depressed. Salty, kind of unshed tears, this cloud of shame and hiddenness. I was defective and my defect was really embarrassing and I would live a life of shame. And I remember the loneliness too of aching for a special friend, the dream of a partner, which in those years, I couldn’t even have. I had little crushes, but it had to be so suppressed.

And so loneliness and aching and sadness and shame, and thank God for the preciousness of that aching, of that desiring. Because that’s what lifted me out of the shame. I used to close my eyes when I was younger and I would think if I really, really, really use my willpower, I can wake up in ancient Greece, where you could be gay. And I remember really being so disappointed every time I opened my eyes, and I was in Long Island.

So, there was high school, where everybody had sex with everybody else and that was high school. But it was a very different experience for me when I had sex with the guys and the women, it was different for me than the other people. And I discovered spirituality, or rediscovered spirituality in meditation with a really well known teacher at that time.

And we had to walk down Christopher Street to get to St Luke’s Church to go to these services. And I just remember being so filled with judgment about these gay people. Not that they were gay, but because sex was kind of so obviously everything, the way that they dressed, the way that they acted, it was all about sex. And I felt such judgment, not knowing that would be me in a few years. But fast forward to many years after that.


How to recognize patterns in your sex life


And I was at my first gay pride parade. And I remember like climbing onto a pole and seeing thousands and thousands of queer people marching down the street. I think it was the first time I ever experienced that this might be something I could be proud of. It was just an electric experience of hope and pride. And I had not ever experienced pride.

But going back to that time, I was kind of moving more and more deeply into that world of intense Hindu spirituality. And in that community, I was asked to be celibate. And I thought, thank fucking God I could be celibate because now I don’t have to think about being gay. And so I was celibate for a few years. My teachers, ultimately, who were these really well-known teachers ended up, this one was having sex with this one and then they weren’t telling each other.

These were really famous, famous teachers and it was shattering to me. And I left spirituality for years. One of those teachers ended up being kind of psychotic. It was just shattering to me. And then I dove into the beginnings of sex. And in the gay world at that time, entertainment was hooking up. Love was found hooking up. The major activity was hooking up. And that’s the world I joined and I got my early wiring from.

And it’s so funny because in a certain way, shame derailed me from feeling like I could be myself in the world because of the kind of heterosexist teaching that I got. Shame taught me that I couldn’t live in the world as me, from the straight world. And then shame taught me in the gay world that I couldn’t be the me that I am either. And in both cases, I was not strong enough to say I’m going to be me anyway.


I had a lot of sex. I mean, a lot a lot a lot of sex. Click To Tweet


And I think of these amazing people who definitely would not have been me, in the twenties and the thirties and the forties before that, in these terrible, terrible homophobic times in our history. How did they say no to shame and say yes to love and have lifelong partnerships? How did they do that? I have such awe for that. And I also have awe for the people who entered into the gay men’s world in New York City and didn’t get lost in that kind of intense and compulsive hookup culture.

But those were not me because I did not have the chops to be who I was and to say no to shame in so many ways. And then in the gay world, as I mentioned, shame stopped me from being really sensitive, tender, vulnerable, highly expressive, bubbly, and kind of exuberant and lots of different things that were not manly and not cool and not contained and not like the hot guys I was attracted to.

So, my shame around my core gift stopped me once again from being me. It was like liberation was not there in the straight world and it was not there in the gay world. And I wasn’t mad about this. I just blamed myself. So, my inability to say yes to me caused so much shame when I was young and then the same kind of thing in the gay world. I couldn’t question the unkindness of the hookup world.

But I mean, it wasn’t that simple either. I was young and I was really horny. And I felt suffocated in intimacy because I didn’t know the skills that a highly sensitive person with some trauma needed to be able to hold a sense of self. And my sense of guilt and responsibility and overwhelming empathy all made it difficult and made it hard for me to have the tools to be in a relationship.

And did I mention rejection-sensitive dysphoria, which is something that many people with ADHD have, which is this piercing sensitivity to rejection. Which I definitely had and still wrestle with. So, what was I doing? I was looking for love in these situations. I was looking for love. I was looking for a certain kind of beauty. And to see if that kind of beauty would be attracted to me, which would define my worth. And that beauty and that physical beauty combined with a sense of toughness or hardness was it for me. Qualities of softness and goodness and sensitivity were wonderful for friendships, but total, total turnoffs sexually. And it was a gradual process that took years.


Sex, Hooking Up, and Love (My Story)

The dangers of hookup culture: Shame was injected like a dye, like an ink.


I got less and less attracted to those types. And as I started honoring my goodness, I began to get more sexually attracted to people with qualities of goodness. And they were more likely to be attracted to me, which was a fucking miracle. Because nothing ever worked for me the other way, six weeks was my absolute maximum. So, to me, this was a miracle. And I knew it had to do with my growth. But I didn’t know at that time that this is the deeper physics of dating. This amazing and almost magical benevolent, hopeful, beautiful thing that happens to us when we embrace our core gifts.

But liberation was not found for me in the gay men’s world, which was my world until years later when I went into therapy and began to honor my core gifts and shift my life to honor my core gifts and feel the intense loneliness of the hookup world that I was living in at the time. And my world changed so much, as the world has changed so much for people who do that same self-honoring work.

And I’ve seen people’s worlds change in my intensives, in my ongoing work, in the lives of people doing this kind of deep, radical, self-honoring around love and romance. When we treasure our core gifts and champion them and dignify them and lead with them, our world changes. So, I want to talk about that in a more universal way. The thing about when to have sex and hooking up and all of that. And what I’m going to say now, these are definitely my biases from my personal experience and they’re not always true.

They were true for me. And I think they’re true for a lot of the people that I work with, but they’re not true for everyone. And with the world of online meeting, the opportunity for hookups abounds in all of these new and simple and easy ways. Now hookups can lead to love. They really, really can. But I think that they’re less likely to, for a lot of different reasons. And one reason is this. I think that for most of us, or many of us, and this is definitely true for highly sensitive people.

When the intensity of your passion and desire is not built on a feeling of safety, when the feeling of safety, the level of safety, doesn’t match the level of sexual intensity, there are going to be repercussions afterwards. So the sex could be really hot and really intense, but afterwards there’s some kind of payback that happens where either you get really needy, or you just want to escape. And both of those are fear of intimacy responses.


The dangers of hookup culture


And I think that having sex too quickly, for so many of us, maybe most of us, is like Miracle-Gro® for our fear of intimacy. And I think that when we get intoxicated in our dates or our hookups, we override all these kind of subtler levels of noticing and discriminating where we might realize that there was something somebody did that we really didn’t like, or it didn’t make us feel safe, or it just kind of rubbed us the wrong way. But we’re intoxicated. So, we’re not going to be bothered by that. We’re strong. We’re not so sensitive. We just move on to fun and we move through those things, or we don’t even notice it. Or because we’re using an intoxicant, we do things that don’t make the other person feel as safe as they would if we were sober. And those are some of the things that happen.

And another thing that happens is we override our own pacing mechanism that requires safety and connectedness. Because sex is so juicy and compelling that it’s easy to build a bridge over our places of uncertainty, unsafety, deep tenderness, deep sensitivity, uniqueness in what turns us on, and certainly any trauma that we’ve had around sex.


Shame was injected into me like a dye, like an ink. Click To Tweet


And I believe that everyone in the world has had some trauma around sex. It may be small “t” trauma, or large “T” trauma, but most of us or all of us have had trauma around sex. If nothing else, because of the culture that we live in. So we build a bridge over those uncomfortable places, and we cross over with habitual and compulsive sexuality, and we don’t deal with those feelings. But they bite us in the butt later on.

And even if the sex is really hot, you could feel really emotionally connected, but ultimately if that connection isn’t bolstered by safety and mutual respect, it’s not going to last. And also, in a way, it’s not real. So, I really do encourage people not to get too intoxicated. I’m not talking about a glass of wine. Although if you have a drinking problem, a glass of wine’s a really, really bad idea.

But I’m talking about not getting to the point when you date where you miss the subtle signals, because there are subtle signals from within you and subtle signals from the other person and subtle signals about the connection and the chemistry. So segueing back to the gay men’s world, it was around that time that AIDS hit and things really changed for so many of us. That’s a whole world of stories and experience and trauma and horror and growth and community and spirituality.


Sex, Hooking Up, and Love (My Story)

Revelations in the gay men’s community: If there was one quality I was most ashamed of it was goodness.


I won’t talk about that much in this episode, but things really changed for so many of us. And even before AIDS hit, but not too far before, there was a movement in the gay men’s community of a 12-step program called Sexual Compulsives Anonymous. And there were a number of what were called S programs, programs around sexual compulsivity. But most of those, or many of them, were homophobic and definitely not inclusive. SCA was inclusive. And so many brave gay men stopped and said, what am I doing? This is compulsive. I don’t want to be doing this anymore. I want this to be part of a journey into a better sense of humanity and the possibility of real intimacy.

I want to create a personalized sex plan that honors my journey. And I personally think all of us should have some kind of a personalized sex plan that honors our journey. Now there was another movement going on concurrently and that was the Body Electric Movement, which was a kind of tantric sexuality program. There were weekends and retreats that you could do that brought people into these levels of ecstasy and realization and spirituality and healing through conscious sex, through deep awareness and very intense breathing practices. And this was a spiritual revelation. And there were these two concurrent revelations going on in the gay men’s community.


Revelations in the gay men’s community


Both of which I respected and adored. And one was Body Electric, which was this tantric approach. And one was Sexual Compulsives Anonymous. And I think, and this is again my opinion, Sexual Compulsives Anonymous lacked the sense of joy and celebration and delight and spiritual potential around what sex could be. And Body Electric, I think, tended to ignore the deep roots of compulsivity around sex in the gay men’s community and maybe didn’t fully dive into how tantra is actually a spiritual practice and is not just about sex.

So, some of these deeper aspects, to me, which were what it really meant to enrich your spiritual life in a bigger, broader, more global way than conscious mutual masturbation or whatever it was, that if you really mean it about growing, you need a regular practice to help you grow as a human being, in addition to conscious sex. Anyway, I adored these two worlds and I saw limits in both of these worlds, and I wished that they could be joined together.

I ran a lot of spiritual retreats for gay bi trans men. And a dear friend of mine, we had lots of workshops in these retreats, and a dear friend of mine had a workshop that he called “Spiritualizing Recreational Sex”. But then he kind of laughingly said, you know what, should I be calling it “Rationalizing Compulsive Sex”? So, these were questions we had and I tried to join them together in my own life as well.

And it was around that point that longing became really intense for me. I had been looking for love in so many back rooms and so many sex clubs. I somehow really thought I would find it there. But I wasn’t built, some people are built to find it there. I was not. And as I entered into therapy, I experienced a longing that had been through my whole life. Because on some level as a gay man, I had a lonely life. And that loneliness was this yawning, vast chasm.

And in that I started to realize that I had friends that were building lives for themselves. And I was like going to clubs and then going to brunch the next day and that was my life. That was my life. And I began to think, hey, those people might be having fun, even though they’re not having sex. Even though they’re not spending every minute looking for love. And this was a revelation and a renaissance for me, where I began to realize how much family meant, which shifted my life also in profound ways. And there were years of asking for help from experts and from friends and really becoming a student of intimacy and of what I was doing wrong.

Fast, fast, fast forward to now and talk about my husband, Greg. And I think if there was one kind of quality that I was most ashamed of, it was goodness. And if there was one quality that I was most punished for, it was fierce truth. And I finally found someone who acknowledged and made space for my fierce truth and who was the embodiment of goodness in so many ways. And that was happiness for me. And that is happiness for me. And it’s a journey where I had to leave behind all the kind of shame-based stuff that I was taught.

I had to work really, really hard to shift sex and hook up patterns that weren’t working for me. And that journey of treasuring, changed my life and gave me my life and my family. So, you know, this is coming out I think like the day after Pride Month. And this year in episode 25, I did a piece about the gifts of queer people to the world community. And I didn’t feel kind of anthemic today. I more just wanted to share my story. So thank you all for listening. I hope it was helpful and useful. And thank you all for being here. And I look forward to seeing you in the next episode of the Deeper Dating® podcast.


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