If you want to cultivate authentic intimacy in online dating, here’s the most important thing to know: It’s not about tricks and gimmicks. It’s about the bravery to be yourself! In this episode, the wonderful Jordan Gray teaches the steps we need to take to do exactly that. There are love-lessons ( and life lessons!) in this episode that are truly not to be missed!

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Show Notes:


  • How to Bring Romance and Authentic Intimacy in Virtual Dating
  • Honest Communication Promotes Authentic Intimacy
  • Powerful Qualities That Attract Authentic Intimacy
  • A Deeply Held Belief in Society
  • Baby Steps Towards Authentic Intimacy
  • An Externalized Conversation on a Best Case Scenario
  • The Most Significant Front-Of-Mind Theme



Authentic Intimacy


How do you bring real authenticity and vulnerability and aliveness and eros to virtual dating. Stay tuned to the Deeper Dating podcast. As I interview Jordan Gray and he teaches us powerful methods for doing that both in our virtual dating life and our real-time dating life.

Hello, everybody and welcome to the Deeper Dating Podcast. I’m Ken Page and I’m a psychotherapist and the author of the best-selling book, Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy.

Today, I’m going to be talking with the truly inspiring relationship coach, the author Jordan Gray about how to bring deep authenticity, romance, and when the time is right, hot sex into your virtual dating life.

Every week, I’m going to share with you the greatest tools 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 skills of love and 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. If you sign up for my mailing list, you’ll get free gifts and you’ll learn about how to use these ideas to transform your own intimacy journey.

You’ll also find a complete transcript of this and every other episode. Also, I just 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’re experiencing any serious psychological or psychiatric conditions, please seek professional help.


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Finally, if you like what you’re learning here, it would be a fabulous thank you if you subscribe on iTunes or elsewhere and left me a review, so thanks so much for that. Now, let’s jump in. I want to introduce my guest who actually I think I did my first podcast interview ever with Jordan. It still really stands out as a very special experience.

Jordan Gray is a five-time number one Amazon best-selling author and a public speaker and a relationship coach with more than a decade of practice behind him. His work has been featured in the Times, BBC, Forbes, Self, Cosmopolitan, Entrepreneur, Elephant Journal, Good Men Project, and countless other publications around the globe. He’s made it his life’s mission to make thriving relationships attainable to everyone.

Since 2009, his writing has reached an audience of well over 80 million people from around the world. In the course of this interview, you’ll see why because the blend of smarts and passion for growth and true authenticity just shines from this guy. Jordan, it’s great to have you here.

Jordan: Ken, it’s so good to be here. I appreciate you having me so much, and yes, the interview that we did three or four years ago still holds a massive place in my heart, so I’m very happy to be here.

Ken: I’m so glad. We’re going to jump in and talk about so many different things, but both of us have agreed that a lot of people are wondering, how the hell do you do a virtual date and have it not be boring or flat or go too far, too fast or not have a quality of aliveness?


How to Bring Romance and Authentic Intimacy in Virtual Dating


How to Bring Romance and Authentic Intimacy in Virutal Dating
Photographer: Dima Pechurin | Source: Unsplash

Ken: What can you do to create virtual dating situations that feel organic, that allow connection, that build connection and that really work to further a relationship when you can’t be together in person? I know you wrote a blog post recently on having wonderful sex on Zoom or a virtual date.

I wanted to expand this to absolutely talk about sex, but also talk about early dating, talk about how to bring romance and authenticity into every stage of the dating process when you’re doing it virtually. I’d love to hear any of your thoughts and reflections on this.

Jordan: Absolutely, yeah, I think the first thing that I want to touch on is really acknowledging that just because there are now screens involved or at least more heavily involved than they might have been before doesn’t mean that the foundational guidelines don’t apply.

Ken: Right.

Jordan: I was talking to someone the other day and they’re saying that “Oh, I’ve been talking to my parents more than I had. I’m talking to my parents more in the last month than I had in the years prior. I don’t know how to have a conversation with them via Zoom.”

I was like, “Well, did you not have a conversation with them before? Are you really blaming the virtual medium or was it just already sticky and that’s just being done, much more highlighted in conscious awareness?

The Discomforts of Doing Online Dating

Jordan: The foundational guidelines of dating kind people and being honest about the truth of who you are and what you’re looking for, these things still apply as much as they ever have, if anything, because we don’t have the distraction of meeting up for a first date with someone and having physical attraction take up a lot of your mental and emotional bandwidth.

It’s now much easier to not drown in our projections and stories of who the person is or who we’re trying to present ourselves at. There’s the opportunity for a bit more rawness and direct communication right out the gate.

I think that is something interesting that I’ve been hearing from a lot of my clients lately is just, “I could hide in certain ways by showing up as my absolute best self in a face-to-face first date, but now with just communication or just a video chat, it’s that much harder to juggle the plates of falsity and pretend that we are something that we aren’t.”

Ken: I love that. There’s so much in that. It makes me think of something Marianne Williamson said where she said, “Sometimes getting naked is the quickest way to avoid really getting naked.”

That’s one piece of this, but the other piece is so interesting what you brought up that the discomforts that we feel in doing online dating are reflective of discomforts often that are there anyway and this highlights that for us.

Jordan: Exactly. I think it is a bit more stripped down.

Up Leveling Your Levels of Honest Communication

Jordan: Even if you do put on a full face of makeup, you can’t hypnotize someone with your amazing perfume or cologne when you’re just sitting and looking at them via FaceTime and that’s the extent of the connection or relationship that you’ve had with them thus far.

Ken: There you are and you’re having a date with someone and you feel this, I don’t know, maybe a flatness or a one-dimensionality because that sexual feeling, that erotic feeling, that romantic feeling, that that feeling of physical chemistry just can’t be there. What do you do at that moment to take advantage of the situation, to make it work, to go deeper? Any thoughts on that?

Jordan: Yes, the most important thing that I would highlight is up-leveling your levels of honest communication. I would say the same thing to people that are in an early relationship but are not self-isolating together, so they’re in separate homes. When the nourishment of physical touch is absent, it’s imperative that you up-level your honest communication.

I do the same thing for people that are early in their dating process, on the first date or even in the first several dates. I think it really behooves people to be as clear and honest and direct about themselves and the reality of their lives and their emotions than they necessarily would on an in-person first date.


Honest Communication Promotes Authentic Intimacy


Honest Communication Promotes Authentic Intimacy
Photographer: Volodymyr Hryshchenko | Source: Unsplash


Jordan: I think that the falseness, because there is a sense of falseness or the diet soda version of human connection, online versus in person. I think that any whittling away of our truth is just that much more felt by anyone when it’s, “Okay, this is through a screen and on person, and so if I’m also trying to hide the truth of my heart or the truth of my core gifts, I think that that sting is felt to a much higher degree.”

Honest, direct communication even more so than you would naturally or appropriately “give” according to the majority of societal dating rules – it’s that much more important to really not hide in the early dating process.

Ken: Wow. First of all, I don’t think I’ve ever heard anybody express this instruction in that kind of a clear way. I just think for all of the countless millions of people, single, coupled, anything – wondering about dealing with the flatness of a virtual screen when you’re communicating, what you just said, Jordan, is brilliant and so incredibly important.

I just want to say that when you’re hanging out with Jordan, which I have never done live, but we’ve done it on video, you instantly feel that, Jordan, you just keep calibrating toward authenticity. Whatever is going on, you’re just calibrating toward the authenticity of your heart. You’re a living example of doing that, which is fabulous.

Jordan: Thank you.

Ken: It’s really true, but so now, I want you to take us through how the hell to do that. I’d like you to take us through that for people who are newly dating.

How to up Level Your Authenticity

Ken: How do you up-level your authenticity, the honesty of your communication, when you’re in a first or second date? I’m going to take you through the whole thing here of relationships, but let’s start there. Any thoughts or reflections you have about that? Any guidance?

Jordan: Sure. I think that in chronological order, one of the most high-leverage things that people can do is really audit your relationship history and see the ways that you’ve either been most prone to hiding or certain aspects or gifts of yourself that you have been the fastest to tuck in your back pocket and go, “This part is not safe to talk about, so I’m going to really put this way on the backburner, on the top shelf.”

Just really auditing where am I most prone to hiding? That doesn’t mean that every person that you go on a first date with and the first 10 minutes of meeting them virtually, especially that they inherently deserve your deepest truths.

“Well, I’m just going to be irresponsible with my energy and just dump all of my baggage at this person’s screen and then expect them to deal with it because,” that’s not necessarily self-honoring either, but yeah, I think really auditing, “How do I hide them most?

If I know that the depth of my ability to love or my sensitivity or my caring or my high-powered career, whatever it is for the individual, whatever those things are, you go, “This is the least safe part of myself to bring.” Really monitor moment to moment, “Did I just go through an hour and a half long FaceTime, Zoom, Skype call with our first date?

How Soon Is Too Soon

Jordan: If I really look back on how I’m showing up, did I make sure to tiptoe around that and avoid it at all costs, and if so, how do I think I’m benefiting from that practice?”

If I were to even allude to, or gently drop hints, that these are significant aspects of myself or important things that I’m looking for in a relationship, I think that is actually much more self-honoring to be direct and clear about, “Well, here’s really a piece of the center of who I am.”

If this is something that is immediately a red flag or something the other person doesn’t want or isn’t at a point in their journey where they are willing to love or accept or appreciate that, then that’s fine and you can save both of yourselves the time.

To me, this is the same thing as when female clients laugh like, “How soon is too soon to let a potential dating prospect know that I want kids?” I say, “As soon as there is any legitimate potential. As soon as there’s any chance of you thinking, ‘You know what?

I’m pretty sure there’s something here,’ you’d want to be honest about that upfront or within the first couple of days instead of going, ‘Okay, well, I’ll just park this until four months in because I don’t want to appear as, fill in the blank, way that I secretly judged myself.'”

Ken: I love this. I think, once again, you’re like hitting right in the center of the center. Just a couple of thoughts on this. I think this is where your workaround authenticity and my workaround authenticity joins so beautifully because that’s the place where our core gifts live.


Powerful Qualities That Attract Authentic Intimacy


Powerful Qualities that Attract Authentic Intimacy
Photographer: Nadir sYzYgY | Source: Unsplash


Ken: We can all ask ourselves the question, “What am I most timid to reveal in my romantic life?” and those are qualities, core gifts, that are nuclear. They’re incredibly powerful. When we hide them, we flatten our beings. When we reveal them, yeah, we’re exposed and we’re vulnerable, but there is an aliveness.

For someone who cares about that quality, that’s a swoony thing to hear people do that to reveal those parts of themselves. I loved that you said that about, “I want to have kids,” because so many women are just trained that like, “You’re just not supposed to say things that scare the man or your partner away.”

I just have to tell a little story here which is a dear friend of mine. She did the rules, all that stuff for women that says, “Don’t chase the man. Don’t say too much. Don’t be too much. Don’t be too demanding.” She did that. She did that. She got some useful ideas out of it, but then she met this guy and she really, really liked him.

It was early in their relationship and they were hiking together and she said to him, “All right. I got to tell you this. I want to have kids. I want a family and I want to have kids. If that doesn’t work for you, that’s really okay, but this feels like it could be going somewhere. I need to say this,” and she was terrified.

He just looked at her and he said, “Where do I sign up?” They’re together maybe 20 years later. I just love that story because she was brave enough to really express what mattered to her. I love what you’re saying.

A Reflection of Inner Beliefs

Jordan: What a beautiful response too. I love the wording of, “Where do I sign up?” It’s like, “Yup, I’m down. Let’s do this. Two feet in? I’m available.”

I think that’s something that doesn’t get enough airtime, is that what you are, especially if there’s been a series or a pattern of unfamiliar relationships or you’ve had five potential partners in a row, that you found the same frustration with or the same thing that they weren’t accepting of or appreciate you over and over, this pattern of people that have been attracting, they’re all a reflection of your inner beliefs which includes your self judgments.

If you attract, to my writing, a lot of women who do have high-powered careers and are entrepreneurs or lawyers and very effective and out there in the world doing big important work and without fail, every single time a client like that comes to me and says, “Oh, all men are intimidated by me or every guy that I go out and meet, they just don’t like that I have a career and they feel small.

They feel like they’re in my shadow,” it’s, at least thus far, always an instance of, “How are you making your career or your power or potency wrong because there’s some aspect of you that thinks, ‘Well, yeah, I am intimidating or I am too much in some way’?”

Because there is that unconscious belief being held, those relegated to the shadow years or decades prior. The script precedes the actors. The script is in her mind.

Creating an Opening That Allows Authentic Intimacy to Come In

Jordan: The script is looking for actors to fill those roles and go, “Oh, see, he’s intimidated. There’s another one, so they’re all intimidated because I am too much. Just like my primary caregiver told me I was 30 or 40 years ago.” Really getting in touch with those aspects of going, “You know what? I don’t have to carry the story anymore.

I don’t have to drop it entirely and have it go from 100% feels real and true to me to 0% I’m over it,” but at least having that sliver, that wedge of doubt of, “Okay, you know what? Maybe not everyone, maybe not all of the people think that I am too much in this way, and if I soften my own self-judgment, I’m creating that opening that then allows me to meet and attract people that also have a more beneficial or positive relationship to this thing in myself that I’m now making friends with.”

Ken: Absolutely, and that’s a formula. If you have a pattern of meeting people who don’t know how to honor a particular part of you, you could be pretty sure that it’s a treasured important part of you that you haven’t been able to fully honor. I just want to say something here because this is a really important point to me, as a gay man who has been very hurt by gender role expectations.

Old Sexism in a New Age Bottle

Ken: When I hear a woman, a high-powered, accomplished woman say to me, “No, but I hear that if I let go of my femininity, I’ll never find an alpha male,” and then some really big important teachers saying the same thing which I think is old sexism in a new age bottle.

There’s this cultural messaging for women about what femininity means and how being too in your power and in the joy of your empowerment scares men away. It’s just crippling, crippling advice. I just pray for the world to change more quickly around that.

Jordan: Absolutely. I think that that’s one of the biggest, I see it as slow and it is happening, but I’m definitely in there, pushing the wedge in further and further and making it the best ability happen faster that, yes, this hyperpolarized 100 %, 0% ideologies of if you’re this gender or this orientation, you’d be extremely this and not the other side. I think that there’s a mass integration happening where people are having it be more of a continuum of, “You know what? I can be 80% this, 20% this or 50% this and 50% this and I can deploy these different energies or tones or temperaments in different aspects of my life with different people and the whole thing is just this ever-shifting collage.”

What could be more healthy, whole, and integrated than having a massive toolbox that you don’t just have access to 20% of it and the rest are off-limits to you but every single tool is available to you.


A Deeply Held Belief in Society


A Deeply Held Belief in Society
Photographer: Larm Rmah | Source: Unsplash


Jordan: It’s the healthiest for your body, your heart, your sex life, your love life to say, “You know what? All of these are available to me. None of these are wrong, or shameful or incorrect. All of these tools are lovable and I’m allowed to deploy all of them in different areas of my life when I use my judgment to do so.”

Ken: Absolutely. That’s one of the ways that the LGBTQ community has helped lead the way in the world. That’s also just a gift and I know that you, and I as a gay man, as a heterosexual man are so committed to that same kind of authenticity.

Jordan: I wouldn’t say it baffles me, but it still fascinates me that one of the through lines of my work that still to this day gets the most pushback is I, semi-regularly, will post photos of myself or articles about the concept of male tears and men crying and how male emotionality is healthy and allowed and great and functional.

I get just hundreds of people, almost exclusively men pushing back and just saying horrendous, nasty things, but there’s a part of me that’s excited by it. It’s like, “Okay, I’m hitting on this nerve that someone really deeply defends.”

If I put out a single photo myself crying and a guy takes time out of his day to tell me that I’m ruining gender dynamics and like, “You have to stop this immediately,” and I’m like, “I’m really touching on something important. There’s a deeply held belief in society that still has not been eroded fully and there’s still work to do.” I welcome it and it’s exciting. I do see us as making progress overall.

How to Reveal Your Soul Qualities

Ken: Me too. This relates to what you just said, because everybody, the qualities that you have, that you hide because they seem too “masculine or feminine,” whatever those qualities are, are nuclear places.

Those are core gift places and they apply to what Jordan just said, the qualities that feel, let’s say, too “feminine” for a man, too masculine for a woman, those are soul qualities and the degree to which we don’t treasure them is the degree to which we’re going to be attracted to people who also don’t treasure them. Super, super important thing.

I just want to operationalize this a little bit more – so Jordan, could you just give an example, somebody who’s in a virtual date, it’s one of the early dating experiences with this person and they think, “Okay, here’s a part of me that I’ve been a little bit ashamed or awkward to talk about, but it’s at the center of me,” how they might do that and reveal it?

Because you also said if you give it short shrift in a certain way, it might not work. I know so many people who share those parts of themselves in early dating, but they do it so timidly that the other person feels awkward too and doesn’t pick up and then the person feels like, “Oh, they don’t get this quality in me.”

Could you just give us an example of how somebody might feel awkward about sharing a part of themselves and how they could do that in early dating?

Jordan: Absolutely. Just to name directly, I think that leaning more towards, being overly clear and overly direct in the presentation of it or the asking of it, I think, it’s better safe than sorry.

At the Risk of Momentarily Neutralizing a Sense of Passion

Jordan: Yes, if you are lobbing out a thing that feels really like emotionally significant for you, but there’s even a chance of, “You know what? This thing that I’m sending off that might feel like a big obvious flare gun might not even be a blip on their radar,” if you’re not sure that it did land, then again, if it is one of the core gift, deeper things you might have held some wounding around in the past.

I think that at the risk of momentarily neutralizing a sense of passion or romantic mystery. I think it’s better to be clear on those things than, “Oh, well, I put out this very subtle hint that they must have picked up on it and I’m going to now mindread and interpret through my bias filters and go, ‘Okay, well, I lobbed out that hint and they didn’t like it, so they probably hate that, so that part about me is still lovable thereby justifying my story or reinforcing it and never just ghosting them,'” because you think that they’re not aligned match.

Just to give a more clear, direct example to continue on the thread that I was talking about before, I’ll just use one from my personal journey where there were so many years of my dating history where I did maintain that narrative that male emotionality was wrong or weak or disgusting or just wasn’t allowed like, “Here are emotions that my gender just are not allowed to display,” if they want to maintain any romantic relationships long term which of course is absolute BS.

Being Comfortable With Honesty

Jordan: But that would be something that I would name in my early dates.

I wasn’t at all opposed on a first or second date, that again, there was any sense of, “Okay, I’m pretty sure this is going well and I’m liking where it’s going and I like everything I’m finding out about this person. I would just directly ask, “How do you feel about it when men cry?” and just let it be there and just get their honest response.

Generally, by the time that I was comfortable enough to be asking this, that was when I was already starting to be on dates with, for me, women who were accepting and loving of these traits.

Whereas years prior, when I wasn’t yet comfortable enough to ask the question if I had just like tried to hotwire the connection and asked it prematurely, I likely would have been on dates with women who would have been like, “No, I agree with the deepest beliefs of your self-judgment.

I think that it is wrong and disgusting. How dare you to even bring this up on a first date? How wrong is that?” I think by the time you feel even tentatively, timidly ready to name the thing, you’re more likely than not, either on a date or soon to be on a date with someone, who will say, as that man said, “Where do I sign up?”

Ken: That’s amazing and really true. I do just want to say like a yoga teacher who says, “Folks, if you need to modify, you can.” Jordan’s an athlete of authenticity. He climbs mountains. He scales cliff edges. He loves authenticity.


Baby Steps Towards Authentic Intimacy


Tiptoe Baby Steps Towards Authentic Intimacy
Photographer: Maxwell Nelson | Source: Unsplash


Ken: If what he said feels like an aspiration, but you’re not quite there yet, notch it down as little as you can, but as much as you need to to make it work for you. If it’s progress and a step in that direction for you, three cheers because you will notice a difference.

Jordan: Absolutely, self-compassion, and kindness and gentleness with your process is imperative at every step of the dating process.

For someone who might hear what I’m saying and be intimidated by, “Oh, that’s like really direct and more than I could ever even imagine myself doing in three lifetimes,” just to give a bit of behind-the-scenes insight as to how I relate to that process, so maybe you can take some tiptoe baby steps towards being the mountain climbing athlete of authenticity.

For me, I just so value my time and energy and heart and the time and energy of others that it doesn’t do anyone any favors to kick the ball down the field for months of dating with someone where there is the very flimsy potential of romantic connection.

I would rather just go, “Okay, here is one of the small handful of things that I’m in touch with that I know, deeply matters to me. If we’re not a values fit, that doesn’t mean that you’re wrong. That doesn’t mean that I’m wrong.

It doesn’t mean that either one of us isn’t enough or that anyone is being rejected wholesale. We’re just seeing if we have an aligned vision for our lives. That’s it. It doesn’t mean anything about us. We’re just checking in and going, ‘Does this work for the highest and best direction of both of our hearts?'”

A Positive Shift of Intentions

Ken: Doing that, going into a date, knowing that whatever those qualities are, that are so central, these core gift places, that your goal and your intention is to share that, reveal it, and only be with somebody who really appreciates that. When that becomes your intention, there’s an amazing side effect is that your fear of rejection diminishes. It actually really does.

This is wonderful and it’s concrete and it’s scary and it’s gorgeous. I love it. Now, I’m going to move on to, okay, so you’ve had a few dates, you’re feeling turned on to this person. You’re feeling a sexual energy. You’re like, “I like this. I like him. I like her. I’m interested,” but there you are on a screen.

How do you bring that in? Any thoughts in that early stage dating where you’re interested? This is a really interesting point because I think we have fears that if we go too far, too fast, it’s going to be like every other time we did online dating and went too far, too fast, and ended up disappointed. I think we’re careful about that.

Then, I also think that we might feel like, “I need to hold this part of me until I actually meet this person and see who they are and what they what I think of them, and then also, it’s a little awkward to bring this sexual romantic stuff up on a virtual date in a way that it might not be so much at a lovely restaurant together.” Give us some guidance on authenticity as Eros enters the picture.

A Guide Towards Authentic Intimacy

Jordan: Absolutely, yes and one point I want to double down on there is both of those pathways are 100% valid. I think that there is validity for some people in following their energy and if there is a mutual sense of trust and alignment and real relationship potential and you want to move more towards the erotic in your relating, then amazing.

Make sure you do it with someone you trust and talk through it in a consent-based way and like, “What are we to us? What are each of us excited to move towards in this process and if there is a sense of all those things are still true, that there’s a lot of passion and intensity and also grounded-ness and potential here?”

I don’t yet want to cross that bridge of bringing sexual charge into a relationship in a video set or video chat sex kind of way and I want to just let this simmer until we’re able to meet face to face even if it’s months from now, that is also fine and you are not slow or rigid or prudish or any outdated words that people might use in the back of their psyche to make themselves wrong. I think both those things can absolutely be appropriate for different relational contexts.

Ken: Let’s say you do the latter and you’re saying, “I’m not really wanting to like go and have like video sex before we actually meet in person,” but yet, it’s also not authentic to just pretend the Eros isn’t there and the turn-on is a beautiful sweet thing and that’s like part of romance and you don’t want to lose that and go flat. What do you do?

The Early Dating Version of Orgasm Denial

Jordan: Speaking in this current worldwide climate, I think there are both virtual and in-person, depending on the city, state, province, country, continent to the person who’s listening to this is coming from, you could go and have a socially distanced, two-meters away or six-feet away walk in nature together just to experience each other in the flesh at all.

Ken: Good point.

Jordan: And even that guarantee of, “Okay, we get to experience each other’s energy face to face and we’re not allowed to touch each other yet,” like that’s its own kind of erotic charge.

Ken: It is.

Jordan: It’s almost the early dating version of orgasm denial for BDSM lovers, like you’re right there. It’s been confirmed that “Yes, I’m even more attracted to you now and I’m not allowed to touch your flesh,” that’s almost like the Romeo and Juliet charge of the forbidden thing. Again, staying within your jurisdictions, legalities.

Going back to the online video chat sex examples, I think that especially in early dating, really making sure that you’re doing it with someone you trust because there is the added layer of this person could take screen grabs or store some of this data if they wanted to.

Just really making sure that this person, there’s real potential and they don’t remind you, they’re not a carbon copy of your last three abusive partners like, “No, this person really does feel safe and soft and grounded and aware of me and compassionate and kind.”


An Externalized Conversation on a Best Case Scenario


An Externalized Conversation On a Best Case Scenario
Photographer: Cody Engel | Source: Unsplash


Jordan: Again, the same rules apply to the type of people that you would be physically intimate with in-person should be as relevant for you know, if not more relevant, to this medium and to build up the sexual tension, the sexual simmer.

I think that having a externalized conversation around what a best-case scenario would look like for both of you, one thing that you would want to do, and once you get a clear picture of, “Okay, here’s what I’m into and looking for. Here’s what you’re into and looking for,” then you can sext around those themes in the lead up to build up the tension.”

Just as you would for a first time and hopefully, it depends on the individual listening to this, but just as you would in leading up to a first sexual encounter with someone, you want to put some effort into your appearance. You want to be as you would.

You want to be discovered naked for the first time with this person. Unless you’ve got a sweatshirt and sweatpants fetish, dressing up as you would for any date, I think, is appropriate when you have the dedicated explicit sexual meetup.

Ken: Wonderful, wonderful. I just want to interject here that what you said first, Jordan, was again, injecting a radical authenticity into preparing for having sex together virtually, and instead of this assumption that we all kind of struggle with is that if we’re really sexually skilled and really gifted, we will just make the other person happy, but maybe the other person is thinking of something completely different than we are. Maybe their sexual and erotic language is really different.

Injecting Authentic Intimacy That Makes a Difference

Ken: The act of saying, “How would you like to lead up to this? How would you like to do this? What do you envision? What feels safe?” is again injecting this radical authenticity that’s going to make a really big difference.

Jordan: 100%. I’m a huge fan of eradicating mindreading from relationships and sex lives. That can come in the form of, really, as you alluded to, really getting in touch with your sexual partners erotic blueprint, what types of things really turn them on, what they love the most, what things are no go zones, what turns them off quite rapidly.

The same thing in early-stage or long-term relationships around if you can have very clear direct conversations of around, “Here are the cheat codes for arousing me or for loving me the most fully.

While anticipating people’s needs and trying to have some educated guesses sprinkled in as nice surprises to show your thoughtfulness and compassion and care for your partner are important, I think that really just allowing ourselves to name directly and have our partners name to us, “Here’s exactly how to win with me in our relationships and in our sex lives,” I think is actually infinitely hotter.

Because you’re actually giving them targeted, calibrated, thoughtful gifts instead of just, “Okay, here we are both just groping in the dark and trying to figure it out as we go.”

That kind of intentionality for me is the ultimate in loving someone. Love someone as they want themselves to be loved and the same thing applies to our sex lives.

A Vision of a More Authentic Life

Ken: Wonderful. That’s so exciting. I really feel like you’re giving us a vision of a braver, more intimate, more authentic, more evolved life.

Jordan: That’s my aim.

Ken: Yes, just another thought on this like homework that we can do in a sexual relationship is to think, “What makes me feel really safe. What moves me deeply in sex? What also really gets me hot and really excites me?”

They’re connected questions, but they’re different questions and that act of first recognizing for ourselves what those things are and then speaking about them is just a beautiful process of evolution.

Jordan: Absolutely. In case there is anyone listening to this and hearing all the talk of safety and warmth and consent as, “Oh, this is just tepid, lukewarm. There’s no way this sex could ever be hot or fun or adventurous in the slightest because we’re killing it with communication.” I would counter that and say that safety is merely the foundation. You’re allowed to have the contextual sense of risk or novelty or adventure in that safe container.

Ken: Beautiful.

Jordan: It’s not that when you’re with a partner you’ve been with for months or years, you have to ask for explicit consent before you go to hold their hand.

We’re not saying take this to the nth degree, just that especially in the context of early dating and the new relationship where there’s potential, that I think that are overly communicating so that you can both surrender and drop into it that much more is imperative upfront.


The Most Significant Front-Of-Mind Theme


The Most Significant Front-of-Mind Theme
Photographer: Rashtravardhan Kataria | Source: Unsplash


Ken: This is wonderful. This is great. Jordan, I would like to give you some time as we move toward closing just to preach, just to say whatever it is that you want to say, whatever feels important to you, whatever you want to share, based on everything we’ve talked about. I’d like to just give you some time to do that.

Jordan: I think the most significant front-of-mind theme for me right now is really just allowing yourself to have the deepest, most fulfilling, most nourishing love relationship of your dreams.

I think that it is very easy to get caught up, especially in our North American culture of this kind of hyper-individualistic, be all that you can be, “I don’t need no man” culture that says, “You are a successful adequate human when you are contributing to the GDP and you need people as little as possible and you’re just this autonomous island of a person.”

I think that we’ve really veered off of that path of allowing ourselves to even admit or acknowledge that we are a social species and we need each other to thrive and the breakdown of greater community is I think one of the greatest travesties over the last 100 years of human history and “you are allowed to want” relationship.

I think that a message a lot of people need to hear is the amount of intimacy, connection, physical touch that you know that you deeply want and crave is not a failing. It is not a bug in your software. It is the most intelligent and correct part of you.

How to Connect With Jordan Gray

Jordan: You’re allowed to just be a soft-bodied human mammal and have social connecting needs. It is not incorrect. It is the most correct.

Ken: So beautiful, so beautiful. Jordan, thank you so much. What a joy to have you on.

Jordan: Thank you so much, Ken. I appreciate you having me on. This is fun.

Ken: I’d like you to tell people, I think a lot of people are intrigued and interested and inspired – by your vision, by how you talk, how you think and what you teach. Could you tell people more about how they could learn about you, get in touch with you, take part in your projects, etcetera?

Jordan: Absolutely, the main hub where everything branches off from is my website, jordangrayconsulting.com. There’s one-on-one coaching. There are video courses for men and women. There are over 500 free blog articles, there’s a lot of resources and my books that can be found on that website.

Ken: That’s Jordan Gray. Could you spell that for us?

Jordan: Sure. J-O-R-D-A-N-G-R-A-Y, consulting.com.

Ken: Beautiful. Thank you. Any last closing words that you have for this community of listeners, Jordan?

Final Words on Authentic Intimacy

Jordan: Date courageously. Be honest about the deepest truths of who you are and deploy patience in finding your lifelong love. The wait is worth it.

Ken: So beautiful. It’s a joy to have you on. I feel inspired toward greater athleticism in my own authenticity, very inspired. Thank you so much for that. Thank you, everyone, for listening. You can find a complete transcript of this episode at Deeper Dating Podcast. You can also join my mailing list there. Thank you, Jordan, once again.

Jordan: Thank you, Ken. I appreciate it.

Ken: Thank you, everyone, for listening and I’ll see you next week on the next Deeper Dating Podcast.


Grab your copy of the Deeper Dating book by Ken Page
Grab your copy of the Deeper Dating book by Ken Page