Authentic Relating: Revealing your truth on the first date with Ryel Kestano — Awake In Relationship
2 Apr 2026 · 35 min
Ryle Kestano, co-founder of Authentic Relating Training International, explains how to bring genuine vulnerability to dating. The practice starts with three things: knowing why you want to date, saying what you actually want, and listening with real curiosity instead of waiting for your turn to talk.
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You are listening to Awake in Relationship, a podcast about intimacy, community, and culture in a time of great change with Silas Rose. Greetings and welcome. My name is Silas Rose, and you're tuned into Awaken Relationship. It's the first day of spring, and it really feels like love is in the air. It's been a tough winter and a tough couple years for many people, but finally, as COVID restrictions are dropping everywhere, there's a possibility of maybe, just maybe, letting our guard down a bit and being open to connection again. The pandemic response really has created what I might call a love deficit. So much of our needs for connection have gone online. I think this has been helpful for maintaining existing relationships, but not particularly great for forming new ones. This is especially true when it comes to dating. For anyone with a heartfelt desire to find a, a lover or a long-term partner, the daily grind of swiping left or right on the dating apps really feels soul-sucking. Rather than make the process easier, the apps have trained our brains to select future mates and love interests based on the most shallow of metrics. There's also something quite abhorrent about an algorithm being the gatekeeper to love. After spending the last 2 years essentially living in our own little bubbles, the whole process of how we create connection can seem somewhat mystifying, which is why I invited my next guest, Ryle Castano, onto the show. Ryle is the co-founder and a coach at Authentic Relating Training International. In this conversation, Ryle and I talk about using the tools of authentic relating to shed our curated online personas and masks and get to a deeper intimacy and connection with others by tracking and revealing our inner truth in relationship, even with a complete stranger on a first date. We also discuss the role of curiosity and following the thread of aliveness in conversation as a roadmap to quickly building trust and connection and even resolving conflict. If you're seeking more intimacy and agency in your social and dating world, this episode's for you. So, Ryle, uh, welcome to Awakened Relationship.
Thank you.
Yeah, so I'm a recent convert to authentic relating practice. There's a group here in Victoria that's been meeting. It just seems like kind of the perfect medicine for our time. And after 2 years of, you know, social distancing and various lockdowns, it really kind of fills a void. How did you first connect with this practice?
I was a student when I first encountered it. I was, you know, pretty much asleep at the wheel as far as any capacity for emotional intelligence or connection with my embodied experience for most of my life. And then started to be confronted with some challenges in my marriage at the time that sort of pulled the rug out from under my feet and was the catalyst for me to really start to explore why I was feeling how I was feeling, why I was reacting the way I was, the beliefs and stories that were coming up in response to those circumstances. So that's what launched me into this world of personal development and spiritual seeking that I had no experience with at all prior to then. And I just tried everything that occurred as useful and valuable recommendations of people sent my way. I worked with a number of therapists, teachers, modalities, went on retreat, sacred medicine ceremonies, everything that I could get my hands on. And in the midst of that surveying the personal development landscape, I was invited to a circling/authentic relating introductory weekend at the Integral Center in Boulder. And I would say near instantly I felt something really impactful and deep and profound. I would describe it as the experience of feeling completely welcome in all parts of me into the space, not only welcome but worthy of other people's curiosity of me and of the parts of me. And I'd never felt that before in a space. It was really healing in some way, and I vowed and in that moment to study everything I could about this practice. And so that, that's what launched me into a deep study that I've been on ever since, I would say.
How long has it been? It's been 10 years or more?
That was in 2013, was my initial experience with it. So I've been on the path since then.
What sort of problems do you think authentic relating solves right now?
Disconnection, isolation, all of the psychological ramifications of disconnection and isolation, anxiety, depression, suicide, suicidal ideation, imprisonment. I mean, we, you know, I started a nonprofit to bring this work into prisons and jails and to support the inmate population in developing the skills to cultivate healthy relationship. And we've now proven directly how authentic relating prevents recidivism among that population because of how it empowers people to create and participate in these qualities, this quality of relationship. So I think it, and because it's so grounded in the relational space, it really promotes people to come into connection and community and to participate in those meaningfully and with their whole selves and to unlock the, vast depths of nourishment that live in conscious relationships and conscious community. And I'll just add too, I think also it speaks— I think it offers the most effective framework for conflict and conflict resolution from, you know, a married couple all the way, I believe, to, you know, governments and at the largest and highest scale we can think of. I think it really promotes a kind of dialogue that leads to people feeling seen and heard and leads to the exploration of a synthesis of people's different values and perspectives into a common solution that can hold everyone.
Yeah, you're really involved in this sort of training element of authentic relating. So you have sort of branched out into a number of different areas. Maybe talk a little bit about that.
Yes, I mean, the very beginning seed and vision was to make authentic relating as available and accessible and easily adoptable and applied to the mainstream audience as possible. And that really had never been done before. It was always kind of constrained to more of the personal development communities and communities that, you know, are attuned to the workshop world. So we really wanted to reconstruct it in a way that could resonate with and appeal to your neighbor, your boss, your coworker, your parents, you know, people who would never otherwise would participate in a transformational workshop. That's who we really geared it toward. And that's what we've leveraged in bringing this work around the world to thousands of people in every culture and country and value system you can imagine. And then as I said, early on I set up, I co-founded a nonprofit to bring this work to inmates. Then we have our artwork corporate division where we bring this work into companies and organizations. And really support them in transforming the workplace culture to one that really values the whole human being.
So when I've gone to these gatherings, you know, they're very fun. You know, it starts off usually pretty light with some sort of game, and then, uh, but it can very quickly progress towards— I won't call it serious, but more intimate— where you get into dyads and, and the questions become more meaningful. It really seems like there's elements of other forms of group process work here. Do you see it as a therapy?
Well, we're not explicitly or overtly trying to conduct any therapy or group therapy. We're distinctly not therapists or trained as therapists. It certainly can be that in being in the practice and relating with these skills and tools that there is a therapeutic component to the experience that arises naturally from the application of the, of the tools and skills. But I'm careful to not veer into a context in which people expect or, or are inside of a space in which, you know, therapy might be being, you know, applied because I, you know, I want to make sure that that's the domain of trained professionals. But for sure, there's no question. I think, I mean, why do we go to therapists? It's to be deeply listened to, to really receive unconditional attention, to be with someone who's going to notice and pay attention to how we're showing up, to identify the patterns that we manifest in our subconscious. All of these things are embedded in the authentic relational space. The listening, the curiosity, the reflection, the ability to see the deeper layers, to illuminate our subconscious. So, you know, there is a lot of overlap there, uh, in which there can be a therapeutic experience.
So you're applying, essentially applying the principles of authentic relating to dating. And you actually have a course coming up called Authentic Dating. How is it different?
Yeah, it's called The Art of Authentic Dating. Yeah, I mean, there's no question that there's an enormous overlap in, you know, just training to be a conscious human being and to participate in conscious relationships, and then how you show up in the dating world. I mean, a date is essentially a precursor to potential relationship, and so how you show up in the date you know, is indicative of how you'll show up in a relationship. And so to the degree that you have any value for being a whole human being in a relationship, to bring all of you to the relationship, to showing up fully, to, you know, conducting yourself with integrity and honesty, to being a trustable person— well, if that's the case in how you view relationship, then all of those should also be, you know, alive and practiced and applied in the dating space as well. So while people are coming to the dating course here to learn how to apply the skills and tools of authentic relating in a dating context, they're also learning how to be conscious human beings in the world, you know. So I'm not saying like, oh, you know, how you show up in the dating world is compartmentalized from how you show up anywhere else, right? It's like you are the common denominator. And so if you're showing up as the whole human being that you are, you know, everywhere, well, then you'll show up like that in the dating world. So the dating course really is about that, but it's also specifically addressing a lot of the, you know, fears, anxieties, issues, challenges, obstacles that often arise in the dating space. But what I think is so unique and exciting about the context of dating is that there's already a value for exploring intimacy with this person, right? It's not just some random person you met at a party or sitting next to on the bus. It's like we're coming in to explore if there is an aliveness in how we connect intimately. And so, you know, given that that's already part of the energetic landscape, you know, it's so conducive to being in the practice of authentic relating because authentic relating itself is a practice of exploring and cultivating intimacy with other people. And so, you know, one of the things that I, you know, teach people at the dating course is to not be so concerned or fixated on the future outcome of this time together, to just let that go and be dissolved and really land here in the present moment. Here's a unique container for you to be with another person in the exploration of intimacy. Where is it that you can, um, do your part so that you and the other person leave that space feeling nourished and seen and uplifted, no matter what happens? Whether you see this person again or you never see them again, there's still this rich opportunity, precious opportunity to drop in with another human being and be nourished by that connection.
Most people listening to this podcast, like myself and you, probably grew up in a materialistic society where that mask is very much encouraged, or I would say even required. And so when it comes to the whole dating realm, the grandmother's wisdom around just be yourself just doesn't really seem to kind of work in the digital age. What are your thoughts around that?
I think that there's an asterisk to just being yourself. It, you know, I think people might misinterpret that as meaning like, well, you know, I can't— I have to just reveal my most vulnerable self 'You know, I have to do all this work on my own to figure out who I even am.' You know, so I would say that if you being yourself is in fact constructing some version or facade of yourself, or if you are in any way enacting a strategy to get some shadow needs met, well, that is also being yourself, and that is also worthy of being revealed and named and shared and offered. I mean, I've often said, you know, I notice I'm feeling insecure right now and I'm trying to control how you perceive me. You know, that is totally being myself, you know, if I, you know, really take that mantra at its spirit, at its sort of spiritual suggestion. So I do think it's sound advice. I just think that it, you You know, it's useful to frame it in a way that has us really welcome all the parts of ourselves, you know, including and especially the parts of ourselves that in any way are trying to manage how we are being perceived by other people. It's so relieving, I think, in the connective space to name that and reveal that to the degree that it's happening.
So central to the practice is really developing that kind of vulnerability, and you specify kind of 3 main practices or ways of being?
You know, I would say often people are bringing all kinds of, you know, for want of a better word, baggage into a dating space. What's this person gonna think of me? Are they gonna like me? Are they gonna judge me? Are they gonna be attracted to me? You know, where is it that I'm, you know, using this relationship to get some need met? Maybe I'm just craving physical contact. I don't even really care about having a relationship. So to be really rigorously honest with oneself What is the why that is fueling the desire or impulse to go out on a date or be in the dating world? Getting really clear about that beforehand. So, you know, we spend a lot of time emphasizing cultivating a relationship and connection with self so that I know myself well and deeply enough to know what are my motivations and intentions behind interacting with someone. And so, you know, I would say one is getting really clear about that prior, like what is my why for participating in this date or in the dating world? And then being really honest and transparent about that, you know, coming into date and not trying to, you know, manipulate the direction of the date in some particular direction, but to be really transparent and open and clear. Yeah, you know, I'm here because I'm looking for a long-term partnership with someone, or I'm here because I'm just kind of casually exploring, this space. I'm not ready to commit to anything yet. So establishing the motivation and the why up front with oneself and then with the other person, I think, creates a kind of orientation to the space that relaxes and relieves and supports people in being their authentic selves. You know, to the degree that someone is coming into a date with something to prove, you know, I need to prove myself to be worthy enough of this person's attention or attraction, that can manifest as a kind of sort of overemphasis on self-reference, like I'm just making it about me. So I would say dissolve that and really pay attention and listen to the other person, you know, almost making that attention a meditative practice, like this— the object of my meditation is this other person and the relational space that I'm sharing with them. So really tune in, and I don't mean just listening to what this person is saying, but watching them. How are they? What are you noticing about how they are? What's their energy? What's their posture? Do they seem relaxed? Do they seem tense? Do they seem nervous? You know, paying attention to these cues and then being able to speak to them. Hey, you know, I noticed you were starting to speak quickly. I'm curious if that might mean you're nervous in any way. You know, so I think paying attention and really listening also means that I'm having to set aside any script that I might have loaded up in my mind, you know, and it may mean that I come to, you know, the other person stops sharing and I have nothing preloaded to say, and maybe that means it's awkward. Beautiful. Let it be awkward. That's a commitment to the present moment without just playing out some script that, you know, usually is quite lifeless and flat. To let that go and really just surrender to the unknown present moment that the listening can infuse, and allowing yourself to go on this ride into uncharted territory. So that quality of listening, and then genuine curiosity. I don't mean curiosity like going through the motions, you know, where do you work and what did you do last weekend and where do you like to go on holiday? You know, those are fine if they're coming from a really genuinely curious place, but to actually tap into what am I really curious about, seeing where it is that my curiosity can sort of deconstruct this notion of what's appropriate and inappropriate, what's acceptable and not acceptable, what's potentially offensive or safe, and really trusting the spark of that genuine curiosity. You know, it's like I can say, I feel nervous to ask you this because I'm afraid it might offend you or have you feeling uncomfortable, and yet I notice like how alive the curiosity is in me. How might that be for you? And there's just— even that alone is so enlivening. And novel and off script? And almost always when I've posed that question, the other person is like, "Ah, exciting, yeah, like what is it?" And then I have permission in some way, I have buy-in and consent to bring these more edgy lines or threads of curiosity. So we have this sort of mantra in the practice which is follow the aliveness. Follow the aliveness almost at any expense. Like, where does this relational aliveness want to lead us, right? And letting it carry us on a journey. So especially on a date, yeah, follow the aliveness wherever it may lead you.
So revealing your experience essentially in the moment is very much the practice. And as you're saying that, it just sort of occurs to me how probably men have a harder time adopting these kind of— this kind of view? Because we tend to— we want to have a goal.
Yeah, it can be. I mean, you know, generally speaking, uh, you know, women are, I think, more, um, oriented to community, to connection, uh, to the relational space, to revealing, to being vulnerable. You know, somewhere in the sort of male masculine lineage is this sort of value for stoicism and just, you know, suck it up and be a man, which somehow means suppress your emotional experience. I don't, I don't think in any way men are having a less rich or less complex or less fascinating emotional experience than, than women are. Um, I think, yeah, in some cases we are subject to this cultural indoctrination that to be emotionally vulnerable is somehow to be weak. And, you know, I don't think that's the case at all. I think it's the opposite. To be courageous enough to invite someone into my relation, into my emotional internal world, I think is very notable and worthy of respect and appreciation.
How is You know, revealing your inner experience like that, how is that different from, say, radical honesty, which sometimes can come off sort of rude or abrupt? I'm thinking, you know, Kramer from Seinfeld.
Well, so that's why it's called authentic relating. It's not just called authentic, right? The practice is not going around and blasting my true authentic experience at people and then moving on. The relating part is such a critical and essential and vital aspect of this practice, and it has to be mated to authentic expression. So where I say, you know, uh, I'm feeling angry at you, you know, I'm upset at you, yeah, well, that's the authentic part that's being revealed. But then the relating part is, how does that land for you? What's that like for you to hear? What's happening for you? What's going on over there? This is the critical piece that links my experience to your experience and us being in a collaborative relational space. And when there is this value for the relational part of it, then I get to say, we both get to say, you know, I can't stand you, I'm so upset at you, I'm angry at you, I'm whatever it is, because it's being offered into the relational space where we're constantly checking for impact and collaborating on exploring and, you know, kind of diving into and excavating the, the, this sort of psychic space, uh, that we are both experiencing.
Earlier on, you're mentioning how these tools can be applied to conflict and Certainly in the whole dating world, ghosting is kind of a phenomenon, an unfortunate phenomenon.
Yeah.
That many of us really don't know how to handle rejection, even giving it or receiving it. Yeah. And so the easiest thing to do is just cut and run. Is there kind of an authentic relating code for either ending a date early, or if it's not going well, or Or perhaps breaking up.
I would say it's true that there is a surge of the phenomenon of ghosting occurring in online, particularly online connections. And I, you know, I think it's easy for someone who has been on the receiving end of another person sort of just disappearing, it can be easy to slip into judgments about the other person, you know, like they don't, you know, screw them, they don't care, and, you know, whatever, they're just a bad person for just dropping me or dropping this. But I think it's useful to sort of step back a bit and look at how the landscape of connections has changed in the space of technology and online, you know, digital social media and means of meeting people. What it's done is while it has, I think, made connection more immediate and available, it's also inundated us with this almost superficial kind of tidal wave of meeting people and initial interactions and multiple threads. And they're all happening in a disembodied way. It's just words on a screen or pixels on a screen. So have we lost that sort of three-dimensionality and depth of what it is to meet someone in real life in a physical shared space? So I just, I honestly think that people are really showing up in the digital realm in connection, dating apps or whatever, I think there's just an over, there's an experience of being overwhelmed by all the multiple threads and trying to feel a sense of humanity. you know, these very superficial, two-dimensional, flat, um, means of communication. Uh, so I think that's a huge contributing factor, and I would encourage anyone, you know, who's on the receiving end to not take it personally. And if it is that you do take it personally, well then that's a useful window into looking at your own patterns, which, you know, would show up everywhere in your life. When we have this whole teaching around what we call the hologram, which is how you show up or how you react how you experience a single moment is how you show up, react, and experience many moments, if not all moments, which is, you know, an indication of the patterns that run us underneath the surface. So, you know, I, I, I think it's useful just to recognize, you know, from a sort of bird's-eye view what is happening in the connective landscape as it shows up in the digital age. But, you know, I To the degree that you are in any connection with someone, just— and if you're not interested in communicating anymore, yeah, just to drop a quick note, you know, I mean, something like, hey, you know, I noticed you don't want kids and I want kids, and so, you know, I'm gonna just end this here because we don't have shared values. Like, that is so considerate, you know, and it's like It's honoring. It's, to me, that's a practice of honoring. It's like, yeah, we, you know, even though we're meeting via pixels and, you know, things flying around the side, flying around the cyber cyberspace, it's like, I, you're a human being on the other end of this, you know, and I still get to be honest and straight and transparent and honoring of you in that space. So, you know, for sure, I, I personally hold the value that I'm not gonna just drop the mic and walk away from anyone. And if I do want to disengage, I will say the reason why as a practice of honoring the other person.
Sharing in such a deep way with a complete stranger on a date really kind of feels risky, but I really believe in a good way. There is a real electricity to authenticity, and you called it an aliveness, and following that aliveness What's at the other end of that? What's the promise if we should follow that thread?
Yeah, I mean, I think just deep down almost everyone, there's a yearning to be seen, heard, and welcomed for who we authentically are, all of our wounds and insecurities and failings and flaws, to be fully loved and accepted and welcomed. With all of those as a part of who we are. And so, you know, for me, the natural trajectory of an authentic conversation, relationship, interaction leads those people to that experience of being truly deeply seen, welcomed, honored, appreciated for who they inherently are deep down at their deepest level. And there's something I think really, um, well, nourishing for sure, but some kind of relief. Like, I— it's okay for me to be here. It's okay for me to be in the world. I feel safe here. I belong here. I would say for sure there's an experience of belonging that awaits, you know, that, that journey. Um, and then it's, it's also the experience of flow state. You know, for anyone who's in a sport or plays a musical instrument with, with, you know, real competence, you have this experience of your ego dissolving into the experience itself, which can be just a profound spiritual experience. It's almost like contacting the divine in some way. And, and that's also a common experience of being in this practice, where there's almost like a flow state that occurs in the relationship relationship and in the conversation where we aren't discrete egocentric beings, but in some way we're just energy moving in this really liberated way. And, you know, I've had those experiences, you know, like say out in the wilderness or with sacred medicine, but where I've experienced it the most readily and consistently has been in authentic relationships and conversations.
So this is probably a good place to end our conversation. Do you want to talk a little bit about the training and how people can find out more about you?
Yeah, sure. I mean, our mission is to share and bring this work to as many people around the world as possible. So, you know, we offer in-person courses all around the world. And we've been in more than 50 locations on 5 continents, uh, and also online. So anybody that can't make it to an in-person course, uh, we have really amazing, rich, deep transformational equivalent training courses online. So the first step for sure is the Level 1, uh, and that's, you know, catered to people who have, you know, maybe tons and years of experience in different modalities, and for people who have never been to a workshop you know, have maybe have a lot of resistance or anxiety in coming to something like this. Like, we're here to really, you know, kind of on-ramp people in a really gentle and, you know, sort of willing way, collaborative, co-creative way. And then beyond the Level 1, you know, people— we want to support people as far as they want to go, right up to where they are willing or ready to dedicate their lives to facilitating authentic relating in the world. So we have, you know, Beyond Level 1, Level 2, Advanced Course, Level 3. It's a week-long residential leadership training. And then Level 4 is a certification program for aspiring facilitators. So yeah, I mean, that's, you know, available year-round. You can go to the website authenticrelating.co, tons of information there. We offer twice weekly free community calls for anyone who just wants to come get a taste and just check it out. Um, so yeah, I want to make it as accessible and easy and available for people anywhere they might be geographically and just sort of in their life trajectory. Like, you know, come check us out and there's a seat for you, uh, waiting.
So, and also quickly mention that you have an authentic dating course coming up at the end of March, I believe, right?
Yep, yep, correct. Yeah, so, um, we're always looking for ways to target, you know, the practice in a way that makes it more meaningful or more resonant or more applicable to people in various different social contexts. Uh, and for sure, I think there's just a huge, um, place for authentic dating to be in the world and in people's lives. So it just felt really right to offer that. We had a really awesome launch program, The Art of Authentic Dating, a few months ago. So yeah, we're gonna keep offering them throughout the year and, you know, really want to sort of shift the paradigm on how we can show up in the dating world.
Awesome. Thanks again, Ryle.
Yeah, thank you. Appreciate it.
If you want to learn more about Ryle's work or Authentic Relating training, head over to AuthenticRelating.com. Co. I'll be sure to put links in the show notes at awakenrelationship.com. If you enjoyed this episode and the content on Awaken Relationship, please consider maybe forwarding this episode to a friend or sharing on the socials. Really helps me to grow the show. If you have any feedback or ideas for future guests, please reach out on Twitter or Instagram I'm also on LinkedIn. I really love hearing from my audience. So thank you, dear listener, for tuning in. Happy spring. Be well and stay connected. Thanks for tuning in to this episode of Awake in Relationship.
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