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Big Swings Only

8 Sep 2026 · 1h 19m · 24 chapters

Episode artwork

Before You Ask AI for Relationship Advice, Listen to This:

In short

Stefanos Sifandos argues that using AI for relationship advice can create “satiation” (feeling understood) without real “sustenance” (nervous-system change and relational accountability). He says shortcuts—AI validation, pleasure stacking, or avoiding conflict—keep people stuck in disempowerment. He reframes rejection as misalignment with preferences/values, and emphasizes healing relational wounds through human-to-human experiences.

Guest backgrounds

Stefanos Sifandos is a relationship expert and coach with 25 years of in-person work, focused on attachment, inner work, and relational healing. The host is not identified in the transcript.

Key claims

  1. AI can reflect patterns and boost self-awareness, but can’t provide real-time attunement or accountability.
  2. Avoidant partners tend to leave first; anxious partners tend to chase.
  3. Inner work requires feeling pain, not replacing it with validation/pleasure/AI companionship.
  4. Unhealed relational trauma drives defensive, hypervigilant behaviors.
  5. Attachment styles form early and can shift with relational practice; secure attachment requires repeated corrective experiences.
  6. Rejection is usually about fit, not personal worth.

Notable examples

  • A woman asks an AI about a third-date conversation; the AI gives “pretty good” answers, which may keep her stuck.
  • Childhood example: an emotionally abusive father leading an adult woman to distrust men until she experiences multiple safe, listening interactions.
  • Dating strategy: grieve past losses, lead with truth/vulnerability, and treat “no” as progress toward “one yes.”

Written by AI. May contain mistakes.

Chapters

2:21

The Pitfalls of AI in Relationship Advice

Discussion on the effectiveness and limitations of AI in understanding relationships.

“People are doing very interesting things, man.”
6:45

Understanding and Healing Past Wounds

Exploration of the impact of unhealed wounds on relationships and personal growth.

“And we tend to, instead of blaming AI, we'll either blame ourselves or blame the other person because that's what's convenient.”
12:30

Moving Towards Empowerment and Growth

Insights on how to transition from disempowerment to empowerment through self-awareness.

“And also what impact can it have on our lives?”
14:03

Navigating Relationships and Self-Accountability

Learn how to set healthy boundaries and understand personal patterns in relationships.

“unquote spiritual for a moment, it's how do we move from disconnection from God into connection from God?”
17:47

Finding Courage After Heartache

Explore how to build courage to engage in relationships after experiencing hurt.

“And it's also a really difficult one to answer.”
20:03

Making Meaningful Changes in Relationships

Discover the importance of seeking support and making conscious choices in relationships.

21:44

The Role of Community in Vulnerability

Understand how community can provide a safety net when facing vulnerability in relationships.

“Or I want to hang around for another hour in your presence, but I don't want to talk about anything just now.”
26:25

Understanding Rejection and Self-Perception

Learn how rejection often reflects others' preferences rather than your worth.

“It's about the other person's preferences and values and the historical context in which they see the world.”
28:00

From Disempowerment to Empowerment

Explore the journey from negative self-talk to empowering self-acceptance.

“I keep experiencing, you know, all or nothing.”
29:00

Understanding Preferences and Rejection

Recognize that personal preferences do not reflect your worth and embrace rejection as a path to empowerment.

“They run in parallel whether we get on that track of empowerment or whether we're not on it.”
Show all 24 chapters
30:54

The Search for Healthy Relationships

Discuss the belief in healthy relationships and how it shapes dating experiences.

“And so you've mentioned earlier in the episode about healthy men, where are they?”
34:32

Dating Apps and Personal Preferences

Evaluate different perspectives on dating apps and the importance of personal readiness for dating.

“It's kind of like the reticular activating system.”
39:28

Leading with Truth in Dating

Learn the importance of honesty in dating and how to attract genuine connections.

“It's easy to just externalize the problem.”
42:00

The Impact of Parenthood on Relationships

Discussing how being a parent influences relationship dynamics and personal priorities.

“And then my friend said, yeah, I mean, usually the only time I get to watch a movie is when I'm on a plane.”
43:38

Understanding Attachment Theory in Relationships

Explaining attachment theory and its relevance to adult relationships.

“I mean, one of the things that's catching a lot of steam, picking up a lot of steam on online is the conversation around the anxious avoidant trap.”
48:37

Navigating Different Attachment Styles

Discussing how to manage relationships with differing attachment styles and the importance of self-awareness.

“But let's say you put in that work, but then your partner doesn't do the same work.”
56:00

Empowering Decision-Making in Relationships

Learn to trust your feelings and slow down for better decision-making.

“negative or positive in alignment with what we want and what we think we want that's fine but don't do that immediately.”
57:20

Lightning Round Format Introduction

Introduction to the lightning round and its quick-fire questions format.

“We are going to do the do-do-do-do-do-do lightning round.”
59:16

Understanding Emotional Availability and Relationships

Discover signs of emotional unavailability and the dynamics of anxious and avoidant partners.

“So the avoidant runs and the anxious cling onto them as they run away.”
1:02:19

Distinguishing Chemistry from Anxiety

Learn how to differentiate between chemistry and anxiety in relationships.

“Listen, I've been married 16 years, but if I wasn't after this episode, I would be dangerous, man.”
1:05:20

Identifying Situationships

Identify the signs that indicate a situationship and how to navigate them.

“What is one thing that good men tell themselves right before they cheat?”
1:08:43

The Deeper Meaning of Marriage

Explore the deeper significance of marriage beyond cultural constructs.

“Listen, I think lightning rounds will stick around, Simone.”
1:13:22

Navigating Relationship Decisions

Understand the nuance in making relationship decisions beyond obligation.

“Especially what I liked about it is the liberty and capacity to self-define what good is for you within your relationship.”
1:17:08

Appreciation and Closing Thoughts

Reflect on the insightful conversation and express mutual respect.

“But man, just the way you re-explain and explain things and just, you know, very heart-centered and just what an honor to be here with you.”
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Transcript

Automatic transcript. May contain errors.

0:00Right now, someone is telling an AI chatbot about the guy she went on a third date with, asking it what to do, and it's giving her a pretty good answer. And that should worry you. Stefanos Sifandos is a relationship expert who has spent 25 years coaching people through this exact kind of moment, in person, in the room, face to face. And he's telling anyone who will listen that relationship shortcuts like using AI are a trap that gives you just enough relief to stop doing the harder work of actually facing yourself.

0:36Stefanos Sifandos: There is no substitute for deep inner work. That is a reactive posture to unprocessed, unresolved, unsettled pain, trauma, feelings that are fractured, that are unwilling to be looked at. And the convenient thing is, let me integrate as much pleasure into my life as I can to mitigate the pain that I'm not willing to feel. This episode is all about moving from disempowerment to empowerment. If you're someone who wants a relationship, is currently in one, or needs to leave one, this episode is a must listen. And in this conversation, he explains why the avoidant always leaves first, the anxious is the one who won't stop chasing, and why a good answer from a machine might be the exact thing keeping you stuck.

1:35This is the story of Stephanos Sifindos, and welcome to Big Swings Only. This episode is brought to you by Granola and Quint. If meetings are eating up your day, Granola is a no-brainer. You can try it totally free for three months. Just head to granola.ai.com. That's granola.ai.com to get your time back. three months free at granola.ai slash kwami find your next fall favorites at quince download the quince app for app exclusive offers or go to quince.com get free shipping on your order and 365 day returns now available in canada and the uk too and when quince asks you where you heard about them let them know it was me that's the best way to support the show okay let's let's Start off with the hard-hitting questions.

2:25So people are dating robots now? Is that what we're doing, Stephano?

2:29Stefanos Sifandos: People are doing very interesting things, man. And when you were talking about this a moment ago, I thought to myself, yes, I cannot wait to go into this because it is not only fascinating, but I think people, we, are going to get a very rude awakening. Ooh, tell me more. Tell me more. Okay. so what i'm observing is happening and and i'm directly experiencing this in and i've been in personal transformation for 25 years coaching leading teaching 25 years and now more than ever i've seen such change in my industry in the space that i occupy and work and live in and people are going to ai and i may say something now it's even in a moment it's even going to shock people what I'm about to say.

3:16Stefanos Sifandos: They're going to AI and they're asking meaningful questions about their lives, about their business, about their relationships, about their intimacy, about a conversation they had with this person that they've gone on a second or third date for. And AI is spitting back to them information. And let me just say that the information that it's giving back to the person is not that bad. It's actually, that's the sort of shocking thing that I think people may think, what? Yes. It's actually pretty informative. And if you frame the question in the right way, I don't know, I'm kicking myself out of a job here, right?

3:49Stefanos Sifandos: But let me continue. If you frame the question the right way, it's going to give you back a pretty meaningful, reasonable response that's grounded in some truth. And so people are becoming satiated with this relationship they're having with AI. But satiation is a problem because self-awareness only brings you so far, in order to make real meaningful change, you have to feel it and experience it not only in your mind, not only in the way you frame the world, your outlook, but in your nervous system. And it has to happen relationally. You have to do these things, make these changes in real time.

4:26Stefanos Sifandos: And so the root awakening that we're going to get is that satiation is only going to take us so far and we're going to slingshot back into human-to-human contact in a really meaningful way. It's just what happened with COVID. The world shut down, people isolated. They liked it for a while and then people hated it and said, fuck this. I'm done with this. I need human to human contact. It's going to happen here as well. So what AI, the conversations you're having with AI are great for self-awareness. They're great for talking points and conversation styles. You can even ask, hey, what do I do? But to be more accountable.

5:02Stefanos Sifandos: You need the human to human content. You need someone being with you, whether it's a friend or a support group or a coach or whatever, a therapist that's working with you in the nuance, in the gray, where AI can't really live there because it doesn't know you in that way. It's not feeling you in real time because it hasn't got that capability. But if you and I have a conversation, even through a screen, but even better in person, I am unconsciously picking, and you are too, unconsciously picking up the way we're interacting with each other, what's really being said underneath what's being verbally said.

5:31Stefanos Sifandos: You can't manufacture that with AI, no matter how hard you try. We're not there yet. Maybe in some Battlestar Galactica future, by the way, 2007 version of that, watch it, or 2004, it's epic. But right now, no. So we think, we're getting confused. We think, oh, AI is doing something for us. It's doing something, but it's not doing what you think it is, and it's not doing enough. oh stephanos this is such a great place for us to start because i think a lot of people would have been surprised by your response because it it it's hard to deny the fact that a lot of times it can be really effective at at helping you really understand yourself it's kind of like yeah yes absolutely because it's kind of like uh it reminds me of carl rogers approach to therapy where he would just hold up the mirror, reflect back your understanding.

6:23You see yourself differently. You start to make the change. But if it's coming from a machine, we don't get that true human connection that actually gives us the true sustenance. So that's the distinction is what I'm hearing. You can feel satiated, but not actually have meaningful sustenance. And as a result, we don't get to where we want to go. And therefore we feel unfulfilled and we don't get the full transformation.

6:48Stefanos Sifandos: And we get frustrated. And we tend to, instead of blaming AI, we'll either blame ourselves or blame the other person because that's what's convenient. That's very unrelational. And that's not healthy dynamics. And you're not learning in real time healthy dynamics. Again, we can perception check effectively with AI. I'm not bagging it. I use AI. If I have an issue with myself sometimes, I'll sit with myself. I have my own practices. I have a men's group that I'm part of, I have peer groups and my wife, whatever it is, like I have people in my life that I can perception check with as well. But I will often also perception check with AI.

7:23Stefanos Sifandos: But that's another thing, like, because it will give me insight. It will help me realize something that maybe I've missed, maybe. But I don't put everything, all my eggs in that basket. And also it's very reliant on the inputs, but also the way you've trained the AI and the instructions you've given it in how to respond to you. By default, it's very accommodating. it's just very I'm going to agree with you it's very agreeable that's not useful because then you're just caught in your own echo chamber and then you bring that same version of you that is unchanged into the relationship and the relationship I'm using a relationship as an example doesn't then shift doesn't change and so you blame the other person but don't blame the other person hold the mirror up just like Rogers did but don't blame yourself either just hold yourself accountable so that you can empower yourself to make the change so when we get caught in these self-awareness loops, we think, or we mistake self-awareness for change or for healing or for growth.

8:17Stefanos Sifandos: It's not. It's a very minute growth at the level of non-action. You're just living in the ether with it. That's not enough. Yeah. I mean, it makes a lot of sense because we can feel good and feel as though we're making progress, but that progress is not real unless it's manifested in the real world. So we still need to have that human to human contact. And now let's make this weirder. Let's make it weirder. I like to get weird sometimes. I love it. Okay. So let's talk about the next level of this, because now we can see how the benefits and limits of using AI as a self check, right? Getting a better understanding of yourself.

9:00But what about the people who are taking it to the next level? They say, listen, man, my heart has been broken far too many times And I can prompt this thing and code this thing in a way that it is endlessly empathetic, incredibly validating, and to be my perfect conversational lover. We're seeing the people who are actually literally falling in love with the AI chatbots. We're seeing some of them that are designed for that purpose, the AI companions. What do you think about that?

9:31Stefanos Sifandos: There is no substitute for deep inner work. That is a reactive posture to unprocessed, unresolved, unsettled pain, trauma, feelings that are fractured, that are unwilling to be looked at. And the convenient thing is, let me integrate as much pleasure into my life as I can to mitigate the pain that I'm not willing to feel and not willing to face. the greater the pain in our lives the greater the pleasure required to mitigate the pain the only way to deal with the pain is not to layer and stack pleasure on top of it or convenience on top of it or validation external or other on top of it it's to actually face and deal and be with the pain that means you've got to feel your feelings so when we're going to AI and creating these circumstances that are validating our existence, validating our beliefs, our ego, our personality, our protective and survival strategies.

10:37Stefanos Sifandos: We're not doing our inner work. We're avoiding it. There is no substitute for inner work, but inner work. And that means you've got to face yourself. That means, once again, you've got to feel your feelings. And you can't replace pain with pleasure. You're just stacking it on top. And I'm not saying avoid pleasure and don't bring pleasure into your life. In fact, part of the quote-unquote healing process is to experience deliberate pleasure, but it's done very intentionally and deliberately. It's not done in the face of avoidance. It's done because your body and your nervous system needs some reprieve, needs some spaciousness, needs some oxytocin, needs some serotonin, needs to soften and move in a parasympathetic nervous system as opposed to being continually jacked because doing the inner work can be very confronting.

11:21Stefanos Sifandos: and doing it consistently without a break or reprieve is probably too much for your body. But turning and orienting towards AI as a solution or as a companion because people are unsafe, people can't be trusted, that is an unhealed wound. That is an unhealed relational wound. And most wounds occur in a relational context and most wounds must be healed in a relational context. Relational meaning human to human or living being to living being, not living being to machine. Yeah. Oh, let's, let us talk about this because this is one of the things about conversations about relationships that I don't think is discussed enough because we often play the blame game.

12:05Whose fault was it that things went wrong? But we don't talk about what is underneath it and the trauma, unhealed wounds that people have to overcome or deal with. Because those wounds often are the seed through which the pain manifests and the maladaptive behaviors come from, right? So let's talk about that. When those past hurts, how do we process them? How do we overcome them? And also what impact can it have on our lives? and our relationships if we don't.

12:42Stefanos Sifandos: If left unchecked, our past hurts that are unintended to will wreak havoc in our lives, really simply put. What does that look like? It looks like destroying relationships. It looks like being hyper protective and defensive. It means that we cannot attune to our own needs and learn to express them in a communicative way that is healthy, compassionate, empathetic. We can't actively listen to the other person. We cannot attuned to their needs. We're constantly threatened by people, therefore we attack before we even give them a chance to share their own selves in the world. We feel lonely, we feel disconnected from others, we can move into self-loathing and self-hate, dislike of self.

13:24Stefanos Sifandos: We are constantly seeking external validation through our performance, So we only believe to be of value in the world if we perform well. Usually all of this is learned at a very early age and it's established at a very early age. And these conditions become patterns and these patterns carry on into adulthood. And so when we leave these parts of us that are hurt and in pain, unchecked, we just continue to suffer and we continue to make the same choices over and over again in order to have a redo, in order to move from disempowerment to empowerment, if I was just to get quote unquote spiritual for a moment, it's how do we move from disconnection from God into connection from God?

14:10Stefanos Sifandos: If I go into a more maybe grounded material sense, it's how do I move from inaction, passivity, fear, contraction, inability to take a meaningful action that's healthy for me to action? In other words, how can I set healthy boundaries? how can I communicate my needs and make requests of other people in a healthy way that still considers them how do I not project not defend not shame not not um blame other people but rather take self-accountability and self-responsibility none of this can really take place if we're not committed to growth now how do we do that because that was one of your questions I'm going to go back to what I said earlier most patterns most wounds like if we talk about attachment theory not just attachment theory but the reality of attachment the reality of how we feel safe in relationship how we give and receive love how we trust or not trust others it happens in a relational context and so if there is a rupture there it has to be healed in a relational context, meaning that we need proof, we need validation, evidence in our nervous systems, in our minds that if we believe quote-unquote bad people existed, we need evidence that good people exist.

15:30Stefanos Sifandos: So it has to happen in a relational context. So if your father was abusive to you emotionally and or physically, and let's say you're a woman in the world and your father was abusive to you, I'm going to use this example, you become an adult woman, as a little girl, you turn into an adult woman and you don't trust men. And there's a part of you that says men are dangerous. Men are just going to take advantage of me. I'm not going to be listened to. I'm not going to be heard. I'm not going to be cared for. My heart won't be held. My opinion won't matter. All men are abusive. You may think that consciously or unconsciously.

16:08Stefanos Sifandos: And until you have the experience, usually multiple times, of men not being that thing, it's very difficult for you to believe otherwise. Now, before you get to that point, you've got to understand your beliefs, you've got to understand your wounds, you've got to understand your patterns, how as an adult you behave in this way and it's linked to these childhood experiences. That's all self awareness and it's all very important, like I mentioned earlier. It's just not the end all. It's not the end point. And then from there, you've got to be in the relationship when you're in conflict, when you're in tension, when you bring your opinion forward and the man says, tell me more.

16:39Stefanos Sifandos: He doesn't shut you down. He doesn't tell you to go away. He doesn't defend himself. He says, tell me more. I'm listening. And your nervous system goes, whoa, what do you mean you're listening? No, no, no, no, no, no. Men don't listen to me. So you push a little harder. I hear you. You're hurting. I'm sorry. Tell me more. What can I do? No, no, no, no. I don't trust that. I don't believe that. So you need multiple experiences of that. So you're going to have to find healthy men, right? You're going to have to, and you're going to have to recognize when they're there and initially will push it away.

17:07Stefanos Sifandos: But if you're committed to your own work and you're committed to your own path, you'll recognize them faster. You'll let them in a little longer. And then things start to shift. Orientation changes. Instead of being myopic in your view, you're more like this. Those maladaptive coping strategies that we spoke to that you mentioned a moment ago, they change and shift. We don't lean on them so much. They're entrenched in the personality and the ego. That begins to dissipate. You start to change your life. I'm giving you a a very high level, very quickly condensed version of how this works to some degree, but it's very possible.

17:41Stefanos Sifandos: And we've got to believe it's possible, but you've got to be willing to do some really meaningful, hard work. Yeah. And it's not just hard. It's scary. It's scary because it requires a lot of vulnerability to say, okay, I've been hurt in a specific way in the past, but the only way I can have a healthy relationship is truly if I put myself in a vulnerable position where the other person could hurt me in the same way today and so because I don't want to gloss over this how and I know it's probably going to be different for different people but how do we build up that courage to put ourselves out there again after being hurt yeah this is a question that in many shapes and forms I get I receive it and it's a beautiful question, right?

18:27Stefanos Sifandos: And it's also a really difficult one to answer. And you already prefaced that by saying, hey, it's going to be different for different people. But here's the thing. There are so many, and I don't claim to know everything in any capacity. There are so many unknowns in our existence, in our reality, in our cosmos. My daughter's four and a half years old, and I've just started asking her, what do you mean in real life? Because you say, oh but daddy goblins aren't real right and i'll say no no darling they're not real but what's real what do you mean in real life so why am i sharing this because at some point you have to make a determination in your life what you will allow to be real and what you won't and at some point you'll have to make a decision in your life each one of us have to do this and i don't know where it comes from.

19:21Stefanos Sifandos: Maybe it comes from hitting multiple rock bottoms. Maybe it comes from having so many multiple past lives, if that's a thing, and all of a sudden something clicks and it changes your purview. Maybe it comes from you seeing something and it changes in your mind, your belief or a perception of how reality needs to be. I don't know where it comes from, but at some point you have to make the all-in decision of I'm going to change my life. I'm going to do whatever the fuck it takes to change my life. I'm tired of this pattern and I'm tired of being tired of the pattern. And that arrival point comes differently for all different people.

20:02Stefanos Sifandos: For most of us, for when I look at the collective consciousness of humanity, it's very easy and I think reasonable to say that it is the rock bottom moments in our lives that create such contrast in our lives that then slingshot us into not wanting that anymore you'll either you'll either take one of two paths you'll the contrast of that deep painful experience will slingshot you into wanting to get out of it and you'll get out of it by making change in your life in this world or you'll kill yourself whether you kill yourself by immediate suicide or whether you drug yourself or alcoholism or destroy your life over seven years 20 years whatever right you will degrade your physical body that decision is a very personal one once you make that decision though you then seek support it's actually not that complex we're relational beings seek support work with a coach work with a therapist join a group see a shaman have a spiritual guide spend more time in with your friends and people that love you and care for you and respect you that you respect and revere and care for and it's reciprocated spend more time in being in relationship doing the confronting difficult scary thing and making different choices in that relationship so if you were usually if you're the type of person that's very avoidant and the moment you have conflict, you're out of there, don't run.

21:30Stefanos Sifandos: Stick around for a moment. Say, hey, I usually like to run when there's conflict and I don't want to do that right now, but I'm just letting you know that I'm really scared and all of me wants to leave, but I'm going to hang around for another hour, which is more than I usually do. So let's talk about this. Or I want to hang around for another hour in your presence, but I don't want to talk about anything just now. Can we do that? Is that okay? These are just relational, mature conversations that we're also scared of having because we're also scared of being rejected because our self-worth is so shot because our sense of belongingness is nil which is a whole other rabbit hole that's my second book belongingness but we'll get there later so i'll pause there i hope i've uh explored enough you you did oh this is great because of all the things that you said there's there's one thing I really want to double click on.

22:21And it is the fact that one of the keys to being courageous enough to take this big swing and open yourself up and be vulnerable is to not just focus on the relationship that you're having with the individual in front of you. It's also to focus on your relationship with others and community because that is your safety net. And because even if you do the thing, you are vulnerable, you open up, and then the person confirms your pre-existing fear and hurts you, you still have that sense of belonging with the community that you've created that can give you a soft landing spot to come back. And I think even just recognizing that can help people feel a little bit more courageous because it's not an all or nothing thing.

23:05Because sometimes it can feel like either it works out with this person or my life completely falls apart. Now we're seeing, no, I can, if, even if it doesn't work out, I still got my tribe. I still have my people and they've got my back.

23:18Stefanos Sifandos: Yeah. That's a very, what you're saying that, that all or nothing mentality is a very neurodivergent, uh, ADHD approach to life, so to speak. So very neurodivergent approach to life in terms of how our brain is wide, where we live and move in extremes. But I want to add something to what you said. You're very perceptive and you just made a very interesting point about the soft landing. So when that person, or if that person quote unquote rejects us. Have you ever walked out of a meeting feeling really good about it and then 10 minutes later, someone's messaging you saying something like, wait, what did we actually decide in that meeting?

23:51That gap between what happened and what anyone remembers is exactly what Granola AI closes. Honestly, the first time I looked back at my notes afterwards, I didn't expect them to be that clean. It was more organized than anything I'd ever written myself and I hadn't done any extra work to get there. Granola AI is an AI-powered notepad built for how people actually meet. You take the same rough notes that you always would, and in the background, Granola AI is quietly transcribing the conversation. As soon as the meeting wraps, it turns all of that into clear, structured notes automatically. And it also runs through your device's audio, so there's no bots joining your call and nothing extra to configure.

24:29It just fits nicely into the tools you already use. You can stay focused on the conversation and still walk away knowing exactly what decided and who's doing what next. If meetings are eating up your day, Granola is a no-brainer. You can try it totally free for three months. Just head to granola.ai.com. That's granola.ai.com to get your time back. Three months free at granola.ai.com. Kwame. The first thing that I ever got from Quince was this pair of really nice formal pants, but they were stretchy and made for travel. So for me as a lawyer and businessman, as I travel and I do these keynotes all over the world, it's really nice to be able to know that I could wear something that looks good in the airport, that's comfortable on the airplane, and I could wear comfortably if I have to roll into a meeting or an event right after getting off the plane.

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26:24Stefanos Sifandos: Say that because I actually don't believe rejection is ever really about us. It's about the other person's preferences and values and the historical context in which they see the world. That's actually it. It's not that much more complex. It's so, like, let's just say someone, it's so true, I mean, think about it. Someone comes to me and they, let's just say I'm single. and I'm sort of dating and someone comes to me and there's a thing there and they're like, no, they're repulsed by me. I'm not doing anything. I don't smell. I don't, I'm not being an asshole. I'm just being me. But maybe they had a really negative experience with someone that had some tattoos when they were younger.

27:02Stefanos Sifandos: And unconsciously that associative trauma is coming up and they're projecting that and layering that on me and saying, you know what? No, you're not my type or I don't want to be with you. Or they don't like the color of my hair or the shirt that I'm wearing or the scent that I have actually, it's still not me. That shit's not me. My voice isn't me. Is my mind me? Not to get too deep into philosophy here. Like it's other people's preferences projected on us. So I don't, I'm not a big thing. I'm not a big fan of saying we're actually being rejected. I think like 99.9 % of the time we're not. That was the side note.

27:34Stefanos Sifandos: Let me go to the point I was actually making. Let's say someone rejects us, right? The opportunity we have in that moment is to not take it personally and to not be with that rejection like we normally have, which is probably contracted, you know, self-beat, negative self-talk. I'm a piece of shit. I'm unworthy. I'm not a good person. I did something wrong again. I am wrong. This person doesn't like me. No one likes me. I keep experiencing, you know, all or nothing. I keep experiencing this no don't go down that path take the take the potential reality of hey this person is just not aligning i'm not aligning or what i represent is not aligning with their values and what they want that's not a me thing because i guarantee you it's mathematically improbable that there's no one out there that doesn't align with you and and so so that's that you know when we start to be different i want to loop this back to disempowerment to empowerment because let me ask you what's disempowering the self-talk the negative self-talk the self-beat the self-loathing the self-hate that i'm not enough i'm not good enough i don't matter is that disempowering or empowering very disempowering very easy to understand what's more empowering you know what thank you for being truthful with me you're not into me thank you for saving me a heap of time it hurts a little bit i appreciate it but i'm not going to take it personally that to me seems pretty damn empowering that's the journey i think our whole journey brother is disempowerment to empowerment our whole life again it's am i in contact with god the cosmos the universe the divine source or am i more disconnected from i closer or further away from it that's it and our actions determine not only our actions that's part of it but i'll just stay on the actions for a moment because it's tangible and material our actions determine if we're closer or further apart And the repetitive nature of those actions determine whether we can get on that line, on that track, because they run in parallel, right?

29:37Stefanos Sifandos: They run in parallel whether we get on that track of empowerment or whether we're not on it. yes oh my gosh this is so good and what you said liberated so many people and what's really cool is that you liberated them not just from that fear of rejection in the future but also gave them the power to reinterpret stories from the past where they might have internalized that pain and said oh it's something about me but one of the things i i say is that you can't negotiate flavor For me, if you talk about peanut butter, peanut butter, it doesn't just taste great. It doesn't just feed my body. It feeds my soul, right?

30:15And if somebody doesn't like peanut butter, I can't persuade them to like it. My son, thankfully, he grew out of the peanut allergy. I was devastated, Stephan. I was devastated. I felt like I was smuggling in contraband every day. but if if they are allergic to tattoos or your religion your race your belief your where you're from whatever that's not about you that's about their preference and just recognizing that we don't need to take that personally is so empowering because now we can have the courage to do what it takes because they're not rejecting you as a person they're just they have their preferences and that's okay.

30:55And now I think it would be a good time to say, to talk to a person who happens to have a program called Be The Queen, this question for the queens out there, because I've got a lot of friends who are single women dating. They are displeased. I'll say that. And so you've mentioned earlier in the episode about healthy men, where are they?

31:25yeah i'll i'll i'll say i'll answer in two ways they are within you and they are everywhere let me attack let me let me attack the first one if you believe

31:41Stefanos Sifandos: good men quote-unquote good men by how you define them aligned men with your values and the life that you want, if you're clear on that, got to be clear on it, caveat, if you believe those men don't exist, then you will never find them. If that belief that lives in you says, yes, there are healthy men out there. There are men that can align with what I need and what I want and what I desire in relationship, then they will be everywhere. They won't be everyone, one but that will be everywhere you only need one unless you want non-monogamy that that complicates things because it's just a game of numbers that that's the complication right but it's it's it's amplified in magnitudes because the complexity of personality and ego and individuation and the history of that a person brings you just amplify sort of like oh three people in a relationship means you say there's two people now there's an extra one it's you know like 50 percent more complex no it's infinitely more complex right because of the way all those patterns are interacting with each other um and i touch on non-monogamy because it's a very real relational container that you know enough people abide by and move into you know move through um but i'll put that aside for a second they're everywhere not everyone but they're everywhere if you can believe that men can be trusted that healthy men do exist and they ultimately Normally that when I say inside of you, when you've healed that wound with the masculine, the core masculine or a specific or specific masculine or specific men in your life, maybe it's your father that hurt you or a past partner or a brother or a bully or whatever it was, when you can heal that within yourself and you're free of that, you're then free to see the inverse, the opposite of what you've experienced largely.

33:33Stefanos Sifandos: and remember what you've experienced if it's been intense and if it's been traumatic it will shade and shape every interaction with man to protect you until it doesn't need to anymore because you've broken free of that relationship to the past and and it's a process right it's not an easy one um but it's so freeing and liberating once it's done and that goes for any wound and any pain, any projection we have or any pattern we hold or any mistrust we hold in the world as well. Yes. And essentially in a lot of ways, it's just the age old truth of whatever you're looking for, you'll find. And a lot of times what we're looking for is confirmation of our beliefs.

34:23Yep. And so we're looking for confirming evidence and ignoring disconfirming evidence. Yes. And so we just orient ourselves in that way. And that's 100 % true. It's kind of like the reticular activating system. Once you start to get in the pattern of seeing certain things, you start to see it more frequently. Like when you buy a specific car, you start to see it everywhere. It's not that there are more of them. It's just that you are seeing them.

34:45Stefanos Sifandos: You're noticing them. It's a noticing. Exactly. It's a noticing. Good. Yes, that's right. Yeah. And that's such a great point that you make. If you just look back, forget about what we're saying, what you and I are talking about, whoever's listening, just literally just pause for a moment and think about your own life and think about how this has unfolded in your own life over the two, three, four decades that you've been alive. For sure. And now let's get a little bit more specific. Let's say hypothetically, let's say there is a lady who says, okay, good. Now I have reprogrammed my mind, Stephanos.

35:20And And now, okay, so now I'm over that. So now if you were coaching a woman who is single and you're trying to help them say, like, run a playbook. Like, what should I do? Where should I be? Should I go on Tinder? Should I go on Bumble? What is the move? What do you think?

35:38Stefanos Sifandos: It's very different for different people. So many women that I work with despise dating apps. Rightly so. They have their own reasons. they don't think they're wrong or right um it's just when i say i'm contradicting myself when i say rightly so so firstly it's not wrong or right to like or dislike a dating app it's a personal preference when i say rightly so what i mean by that is that they're aligning with their values and their preferences and their preference is to meet people quote unquote in old-fashioned ways meaning in in person right not through a digital interface some people don't care about that that's not limited to demographic.

36:18Stefanos Sifandos: I know women that are in their forties and fifties and sixties and absolutely love dating apps. They have no problem with men. It's not coming from a, like a wounded place where they're scared to be seen or anything like that. They just actually, they enjoy the possibility of meeting more people at a faster rate. Um, and in really interesting ways that they couldn't access before, right? Some people just dislike it because it doesn't feel personal and they don't trust the app and they don't, they want to really feel the presence of a man, right? So just personal preference in terms of dating apps, in terms of strategy.

36:53Stefanos Sifandos: What I say to women that are dating in this way, you've got to ensure that you've grieved the life you haven't had, the previous relationship that didn't go the way you wanted it to go, that you've grieved your own losses in life, that you've, and I'm not talking to completion. It's not about arriving at perfection. It's ensuring that you've created enough space in your emotional and relational body, your spiritual and physical body to say, hey, I'm ready to date again. And then you'll date based on your preferences. Lead with vulnerability and truth. Lead with what you need. Lead with what you're looking for.

37:32Stefanos Sifandos: Lead with honesty. These things are not easy you said this before man you're very you're very astute i'm hearing how you're responding to me and how you're um interpreting what i'm saying or rephrasing what i'm saying and it's really beautiful and so i say that because we have to be able to communicate what we're attuning to in our environment and so many of us don't practice that enough right Right? And when we do that and we lead with that, and it's scary, right? Like, because we're putting ourselves out there. When we're being truthful, we're not putting a mask out there. The justification is, well, and this is more unconscious.

38:12Stefanos Sifandos: If I lead with what I think people want, but it's not really what I want, but I think it's what he wants or what people or men are looking for, and that gets rejected, I'll be okay. It hurts less. but when you lean with your absolute truth in the moment and it's not met with reciprocity in any capacity and or it's mocked or ridiculed that hurts more but you've got to get yourself to a place where you can do that because that's because what you're doing is the more no's you get the more yeses that come to you right again we're only looking for one person you want a lot of no's because it's all those no's it's all those half no's that lead you to a full embodied yes and a full embodied truth.

38:52Stefanos Sifandos: You've got to be patient. You've got to trust the process, trust yourself. And so I say to women, you've got to grieve your past, grieve what wasn't, grieve what was, how you wanted it to be different. And from that place of clarity and spaciousness that lives in you, if you can act in accordance with truth and be in service of beauty and beauty and truth is synonymous, as is love and growth, you will naturally evolve into the relationship you want to because when one comes to you and it doesn't align and this isn't about being again not about being perfect not about being rigid not about having a a stickler checklist it's not about that when it comes to you and it doesn't align intuitively intellectually somatically all of that you say no to it and it may hurt but you'll say no because you value your truth more than just i'll just settle no that's not where you want to be i for me what the thing that's most empowering because I love the fact that everything that you're teaching and talking about is rooted in empowerment and which is vastly different from the majority of dating content out there because it's far easier for me to just be like, yo, he's a narcissist.

40:05That's why things messed up. Or she's selfish. That's why things messed up. It's easy to just externalize the problem. But for you, it's rooted in empowerment because now we can actually do something. There's something meaningful that we can do to have a meaningful impact on the outcome that we want to see. And the most powerful part of this empowerment is the reframing around rejection. You only need one yes. Only need one. And so it's almost like we are in the past before we could say, yeah, I'm afraid of rejection. I'm taking it personally. It hurts me. It triggers those past wounds. But now we're saying, I need to get these people who are not mine, not for me, out of the way quickly.

40:47So the faster we can get to that no, the better. And what's funny is that you're giving us a strategy that, again, flies in the face of what a lot of common, not explicit dating advice is, but kind of subconscious unspoken dating advice is, where you say, hey, listen, make yourself as generally attractive as possible, even if that means some deception. I remember I was talking to a friend, this friend shall not be named, and they said, I looked at their dating profile and it said um interested in kids yes i was like bro you're not interested in kids i know that he's like well how else am i going to get in the game i said eventually this is going to become an issue at some point he's like you have to understand how to play this game so i'm going to send him

41:32Stefanos Sifandos: this episode yes and in the episode because he's only hurting himself yes he's hurting other people but he's hurting himself man like that's the thing like you lead with a mask you're going to attract mask wearing individuals it's standard right like if if there is there is no substitute for truth and if he genuinely that's and that's a big that's a deal breaker for i'd say nearly a hundred percent of people if not a hundred percent like yes or no to kids it's a deal breaker man because it's life-changing you're a father you know like it's it is we're talking about it this morning i have a every wednesday morning i'll a group of guys to my place and we just we hit it hard like we just train hard right today we just lifted heavy stuff walked with it and and did a lot of um sprint work and whatever right so but we were talking about not everyone's a father but most of them are fathers um and we were just talking about um quiet times talking about the odyssey and when are we going to watch the odyssey then we're talking about should we watch it on 70 mil imax authentic or should we just what and i I said, man, I'll just watch it on my laptop and it'll still be good, you know?

42:42Stefanos Sifandos: And then my friend said, yeah, I mean, usually the only time I get to watch a movie is when I'm on a plane. And then there's three of us there, four of us there. And we all said, yeah, it's quiet time. That's like when you're away from the kids, so to speak, right? And I said, yeah, quiet time, the most valuable asset a father, you know, a parent can have. So, you know, to the point of kids, yes or no, like there are women out there that don't want children. Not every woman wants a child. or maybe there's women out there that have had children and don't want any more or whatever it may be right or they can't have children or they just what there is someone out there like him that maybe doesn't want children yeah that is that is what i'm willing to bet my entire net worth or my left arm i like my left arm on that fact that there are women out there and men that don't want children and there are women out there and men that do i get it you limit your pool but that's what you want to do you said that a moment ago and i agree with you limit your pool to have a better quality pool to choose from.

43:40Right. Oh, powerful, powerful. This is great. I mean, one of the things that's catching a lot of steam, picking up a lot of steam on online is the conversation around the anxious avoidant trap. So we're seeing a lot of material around the different attachment styles. Can you just give us a brief overview of what attachment theory is, but more so the relevance it has, especially in relationships? Yeah.

44:07Stefanos Sifandos: So attachment theory is formed at a very early age, right? And it really, it's a model. It's like a psychological model. And it's all about the emotional bonds that we form with our primary caregivers. I use the term, you can say parents, but not everyone has biological parents. It could be grandparents. It could be foster parents per se. It's just our primary caregivers. and they shape basically and i mentioned this earlier about how we give and receive love how we trust how we love and how we ultimately connect not only in our childhood um teenage but largely our adult relationships right and so there are um the core styles are secure and then there's insecure anxious insecure avoidant and there's also disorganized which is a combination of both avoidant and anxious and so um let me what's his name is it josh or john john john uh john bulby so john bulby but there was a mary that's right mary ainsworth john bulby they are sort of the the pioneers of this work and that expanded through and it's again it's it happens at a very early age um you know infancy to oh no maybe two or three years of age somewhere there where these attachment bonds are formed and when you're secure you're not going to have issue you're going to trust that a parent can leave the room or a primary caregiver can leave the room and they'll come back right um when you're insecure anxious that's going to be tough like you're not are they going to come back um i'm worried that they're not going to come back i'm going to start crying, I'm going to start stressing, I'm going to start doing all of these things as a little baby to try and get their attention, that carries over into adulthood.

45:58Stefanos Sifandos: But in adulthood, it may appear as needy, it may appear as texting 15 times in the space of 10 minutes, it may appear as panic, it may appear as asking too many questions too soon, like wanting too much information, needing to have resolution and conflict resolution and communication immediately. whereas that um insecure avoidant is indifferent if the caregiver's there if they're not um actually avoids them upon return these are all survival strategies by the way so that parries over into adulthood if someone is indifferent to them they turn their backs if there's conflict or a difficult situation they turn their backs whether they physically leave the space or they emotionally check out and disassociate right the disorganized is is like i said it's a mix of of both of of insecure of sorry of anxious or insecure anxious and um or you know insecure i think it's called insecure resistant now from if i'm accurate on that um as opposed to in insecure anxious and then insecure avoidant i'm i'm personally disorganized so and not so much now like i'd like to say i have quite secure attachment now um but my my primary because you can you can shift this like with with inner work and practice and you know quote-unquote therapy um and and being deeper relational in in relationship and doing differently you can absolutely shift these and move into secure attachment with other human beings and with yourself right um you'll often experience people often experience disorganized when there's a lot of volatility and uncertainty in a household a lot of um maybe maybe violence just unpredictability chaos um you know there's calm there's peace and then there's not um and that can often shape the disorganization of a of a child as well just to i can just speak directly to that myself you know yeah wow this is powerful because we can see how those what was formed in childhood really has significant ripple effects throughout the entirety of your life without if you don't do anything about it but again going back to that foundation of empowerment you can do the self-work to get to the secure attachment.

48:14And I think that's really powerful. And on the other side too, one of the things that's really challenging though, is you might be in a relationship and each person might have their attachment style. And then you work hard, you get to a secure attachment. I make it sound super easy. It's not. It takes a lot of time, a lot of self-work, a lot of humility and vulnerability with yourself and self-awareness to get there. But let's say you put in that work, but then your partner doesn't do the same work. How do we navigate somebody else's attachment style? Because they're in the relationship too.

48:49Stefanos Sifandos: Let's talk about values for a moment. And this might take care of the attachment styles or competing attachment styles, right? And so if you're committed to growth and doing the work in a relationship, and one of your highest priorities and values is growth and your partner is unable and or unwilling to grow with you in the ways that you really value in a relationship and they're not committed to growth, you have to make a decision whether that's a non-negotiable for you in the relationship and in your life and in the kind of relationship you want to live. I have had instances where specifically women have said to me my partner is not really interested in growth i'd sort of i'd sort of not argue a strong word i would posit differently but i'll explain i'll share their stories anyway which are very similar i say my partner's not interested in growth but he's so amazing in so many other areas of life that and growth is so important to me but he's so nurturing he listens he's caring he does this one like there's all these things that they can list very clear and they say like even though he doesn't really value growth he doesn't come to the seminars he doesn't read the books he doesn't he's just such a sweet human i love him so much and i just want to be with him i would say but i think he does value growth just in a very different way and and and and so you it's very individualized you've got to you've got to and this isn't about you know i want to tell them that they're wrong or right about growth it's irrelevant it's like how you both match with each other you know wow and i think that really really matters and to my to your point around the attachment piece now let's use a little bit more of an extreme example or a more a more i should say prominent example let's say you're doing your work and you're really tidying up your anxious attachment right and you're getting to a place where your partner can disappear and you're actually regulated in your nervous system you feel calm and grounded but you also say hey like i don't appreciate how you're being when we're in conflict my request is this and they're not making that request because they're still in their avoidant patterns and they're unwilling to do their work you're going to make a choice like can you be with that are you okay with that you seem to be okay with yourself like you seem to be secure or are you just going to keep getting activated eventually and is that going to ground you because here's the thing right if if you're a heroin addict and you want to quit heroin i think living and sleeping and eating in the heroin in the smack house ain't going to be very useful particularly at the beginning so you've got to make that decision on how important growth is to you and your needs in the relationship yeah just notice one thing i said sorry just one And notice what I didn't say.

51:45Stefanos Sifandos: I didn't make it about the other person. How you value growth and your needs in the relationship. Oh, my goodness. You're giving people no excuses because we cannot externalize success here, right? Because essentially, you know, let me echoes of negotiate anything. Deal or no deal, does it work? Right? Does this work? And at the end of the day, we can psychoanalyze this to death in a way that becomes a little bit performative where we say, well, their attachment style is this. And so I'm trying to do that and blah, blah, blah. Essentially, you're saying, hey, either you're compatible or you're not.

52:23And you have to make that decision for yourself, even after you do that self-work, whether or not this works for you. If it works for you, fantastic. If you can make it work, fantastic. But if it doesn't work for you, you need to be honest with yourself and the other person and set effective boundaries and then make the best decision for you. Again, it doesn't mean that it's easy to make that decision ending a relationship or anything, but it is still within your control to recognize, hey, I have the full right and responsibility to make the best decision for myself. And it's rooted in compatibility.

52:55so you it's it sounds like it's more important for you to understand your own attachment style so you can kind of have a map so it's not a diagnosis where this this is not going to change you say this is where i am now and this might be where i am now on this map and i am navigating to secure attachment for myself the other person they're on their own journey and i need to ask myself whether or not i'm willing to be on that journey with them and that really is the end of the analysis. It could be helpful to say, you know what, I can hypothesize about their attachment style. So maybe I can anticipate some things.

53:32Maybe I can make some adjustments that are still authentic to me, aligned with my values. But at the end of the day, it just really comes down to compatibility.

53:39Stefanos Sifandos: Yeah. When we, very well said, when we focus on the externals, all we're really doing is the attempt to apply control in our lives. And control is fruitless. And that's just the tool of the personality. I'm scared, so I want to control. That doesn't mean now, and manipulate. It doesn't mean that we don't have honest, earnest, open conversations with our partners, right? We actually, we need to. And we want to communicate with them. And we want to sit back and observe what happens when we make a statement, make a request, state a need, share a truth. How do they behave and interact with that? Not just once, but consistently over time.

54:25Stefanos Sifandos: I've heard you speak on multiple business podcasts. I'm pretty sure it was you, right? The reason why you're very proficient and very well regarded in the space of negotiation, largely in business, right? Sure. is because you understand relationships understand psychology human so it's just that's what it is and when i was listening to you i would say this was i just i just had a recollection now this is why i'm mentioning this it's like i was training my garage to have a home gym this was months ago it could be at the beginning of the year i was just listening to this business podcast i can't remember which one it was and you were being interviewed and i'm like oh this guy oh he knows what he's talking about this is awesome because i was seeing everything i tend to most things through a psychological emotional relational lens yes i was just interpreting you doing the exact same thing and so i just wanted to mention that because it just came to me but importantly as well sit back state your truth put it in the space and shut your mouth be quiet listen it's all information if they turn around and walk away and they keep doing that that's information information if they argue and defend become defensible and blame and shame and make excuses information if they get curious about you if they're attentively listening actively listening asking questions information it's not neutral or sorry it's not positive or negative it's just neutral is how what meaning make we're meaning making machines we're going to make it means negative or positive in alignment with what we want and what we think we want that's fine but don't do that immediately.

56:06Stefanos Sifandos: Just listen. Put it out there and slow down and absorb. That's going to be the best thing you can do to make your decision. I don't want to disempower you and say, here's the three-step or seven-step framework, which I have plenty of them, by the way, on what you need to do. Sure, but the one thing you need to do, maybe two things, is be in your truth to the maximum capacity you can be and then pause that's it that's a two-step process i love this man and hey listeners you see this budding bromance in front of you this is amazing i love it and that's the thing when people hear me respect for you thank you man appreciate that and it's the the work that you do is so important because we're doing like essentially the exact same work just in different contexts and i it's funny because when people hear me speak they're surprised because they expect, oh, he's a lawyer.

57:01So that's the angle. And then they're really surprised that they approach. My undergrad's in psychology. I wanted to be a therapist. So you see that come out so much more. And this is great. Again, always rooted in empowerment. I love this. And now, Stephanos, we have gotten to the most exciting part of the interview. We are going to do the do-do-do-do-do-do lightning round. Simone, don't edit that. That's the best sound we could ever have. Keep those doodos in there. Okay. We're doing this. Okay. So we're going to ask you eight quick questions. Um, and let's see what we can do to get quick responses.

57:43And then after that, Simone will come in at the end. You ready to rock?

57:47Stefanos Sifandos: Let's do it. All right. What is one sign that someone is emotionally unavailable by date number three. They still haven't asked you a question about you, but they're still talking about their accolades, the things they've done in their past, and they haven't even really got to know you. You've even fed them lines. You've even given them every opportunity, but very quickly it orients towards them. Oh, this is good. Oh, this is so good. And, you know, it's funny. You know, this. Wow. Man, you're good. You're good. No, Kwame, lightning round. Stay on topic. Okay. Number two. Okay. We have one person who's anxious, one person who's avoidant in the relationship.

58:41Who leaves first? Who leads first or who leaves? Leaves.

58:48Stefanos Sifandos: Oh, the avoidant is always going to leave first. They are looking for any excuse to not be in the relationship when the going gets tough. The going gets tough. The tough doesn't get going because they're not tough. They have no resilience. They don't want to stay in there. And so, by the way, the anxious is the same. Their act of non-resilience is by being clingy and desperate and needy, right, instead of actually feeling their feelings. the avoidant is going to run out of there so quick physically emotionally they're going to shut down they're going to distract they're going to go drink alcohol they're going to have sex with other people they're going to immerse themselves in their work they're going to distract massively and until they really make that wound whole and it only can happen in relationship really especially for the avoidant by the way the anxious is a little different their work is actually out of relationship just as much as it is in but the avoidant is particularly in relationship until they actually stick around and face that discomfort of that thing that they're feeling, they're going to keep running forever.

59:50So the avoidant runs and the anxious cling onto them as they run away.

59:54Stefanos Sifandos: Oh yeah. Oh yeah. Perfect storm. Okay. Ooh. Is a good morning text to an ex micro cheating? Yes and no. It can be. what are your agreements in your relationship these are defined by your values the values you bring as an individual the values your partner brings as an individual if you believe that that good morning text is out of integrity and your partner would be disappointed hurt upset and or you actually have agreements around how you communicate and you're breaking that agreement then it's quote-unquote micro cheating meaning that it's dishonorable or it's dishonest If you have agreements around how you communicate and what you're doing, then no, it isn't necessarily cheating.

1:00:47Stefanos Sifandos: So it's very context and situational dependent. You know, people know when they're cheating, whether it's a micro cheat, emotional, physical or other, you know if you're out of integrity. So what is one boundary that everyone should set on date number one?

1:01:06Stefanos Sifandos: it's more of a commitment and if the commitment is broken then a boundary is broken and the commitment to me is do we both promise no matter how long we are together for how many dates we have and what this becomes can we be in the highest service of beauty as often as possible not wearing masks. In other words, can we serve truth? Can we be explicitly and implicitly clear on the truth that we want in this relationship, what we need, where we're at in life, what we've worked on, what we believe our deficits are, where we believe our fears live within us? I'm not saying you have to share all of that on date one, but on day one, if you're dating with intention and if you're dating to be in a long-term relationship, let me just put that caveat in there because if you're just dating for casual whatever, I mean, I still think being in service of beauty and truth is awesome, but there's going to be less revealing.

1:02:07Stefanos Sifandos: There's going to be less depth traverse, right? But if you're specifically dating intentionally for long-term relationship, make the commitment and the boundary. Hey, can we be in service of truth? Yes or no? It's that simple. My goodness. Listen, I've been married 16 years, but if I wasn't after this episode, I would be dangerous, man. I would be like the best person on the market. My God. I think about myself, too. My goodness. At least I would hope I would be. I know. Jeez. Okay. So we have. Oh, chemistry versus anxiety. How do you tell the difference in the moment? Hmm. So chemistry is going to feel, I'm going to create a distinction between the two, right?

1:03:04Stefanos Sifandos: And then I'm going to create a similarity between the two. So chemistry is going to feel very chaotic and anxiety, when they're different, chemistry will feel very chaotic and anxiety will feel more like tension and contraction and almost this confusion between fear and intuition, right? I'm going to stay on this line of delineation for a moment. Chemistry is more related to limerence, less related to lust, so to speak. Lust is this pure biological, physiological drive that is saying I'm magnetic and physically attracted towards you. That lust, the limerence or the chemistry is more rooted in disorganization and dysregulation.

1:04:02Stefanos Sifandos: It's more psychological. It's more that a massive attraction is needed because it's really attracting from a wounded place, attracting from a painful place that's unresolved. And the reason why you're coming together is to have some resolution possibly, but you've got to know that to actually be able to be different, move from disempowerment to empowerment and not be controlled by your patterns. where the anxiousness and the chemistry can almost blend is that they're both more related to that limerence and they're both just chaotic and they're both fear-based and they're both around contraction and there isn't really that much distinction between them.

1:04:41Stefanos Sifandos: And the anxiousness is there because you know that you shouldn't really continue with this relationship, but you're so pulled towards it or you're pushing yourself towards it because basically you're attracting from a familiar pattern. You're attracting from familiarity because low self-worth or in and out relationships or unavailable men or unavailable women have been your norm. And so the anxiousness and the chemistry blend. Wow. So sometimes it's one or the other and sometimes it's both, which is scarier. I tend to feel that. Yes, I believe so. Amazing. Amazing. Okay. Oh, my goodness. What is one thing that good men tell themselves right before they cheat?

1:05:37Stefanos Sifandos: I'll never do it again. This is the first time. I deserve this for A, B, and C. you know we haven't been intimate or we're disconnected anyway or i need nurturance and love and i haven't received it all the justifications that can take place i really like the framing of the question i think it it de-demonizes um the person and focuses more on the action, you know, because, and I'm not justifying any action that is out of integrity or that hurts other people. God knows I've done that many times myself. And, you know, I've caught, I have regrets around that. And I've also found that the more I've shamed myself in the past and demonized myself in the past, the more I actually did it because it just puts us in this vicious shame spiral.

1:06:35Stefanos Sifandos: And in order to get out of the shame spiral, you know, we go to what's pleasurable, the greater the pain the greater the pleasure and so it just repeats itself so those good men will say anything they need to to to have what they believe they want or need and then at some point man you got to ask yourself the question right like what defines a good man which is a whole or a good person or a good woman right it's a whole rabbit it's a big rabbit hole yeah so it It sounds like it's almost like a drug where you just begin to self-medicate and numb through the constant seeking of pleasure. That's good.

1:07:17Okay. These questions are so good. Okay. What is the fastest way to spot a situationship before you end up in one?

1:07:33Stefanos Sifandos: when you're already looking metaphorically or physically for the exit you know you're in a situation ship when you know you're only bringing a partial version of you into the situation ship or into that dynamic, it's a situationship. When you don't fully trust the other person and or yourself, it's a situationship. When you're lying about what you really want and need, which is related to the truth piece, but more specifically around long-term versus casual, and you're saying you want a casual relationship, or the other person is, right? But really, you know, sorry, you're saying you want a long-term relationship, but really you're just there for a casual relationship because you don't want to commit.

1:08:25Stefanos Sifandos: that's a situationship. When you are non-committal and you know you're not going to commit to anything of substance or long-term, not to say that short-term relationships don't carry substance, they absolutely do. But when you're in denial or lying about that or both, it's a situationship. Man, this is so good. Listen, I think lightning rounds will stick around, Simone. I think this was pretty good. I think this was pretty good. You crushed that. Crushed that. okay listen before we wrap up let's bring simone in you you've done a ton of research i know you've been listening in simone what's on your mind uh when is uh how do you know that someone is the right uh person for you to get married to so for the reason why i ask this is because i have two uh friends these guys are brothers are twins actually and they are getting married at the same time a double wedding so i was talking to them and i asked them why are you getting married so one of them told me because i've spent seven years of my life with this girl and the other guy told me i am getting married because i love her so are those real reasons for them to get married i asked my daughter yesterday what's real darling what's real real reasons an interesting question um so your original question was how do we know it's the right time to get married essentially yeah sometimes we don't know it's not an intellectual or a cognitive choice that we make and it's more an intuition an alignment of our physiology an inner knowing, a trust, even some logic and rationale that lines up and says yes to this thing, right?

1:10:28Stefanos Sifandos: So much of our lives are culturally constructed, as is marriage, right? And there's something deeper to marriage and to union that, if we allow it to, can really shape the trajectory of our lives and shape our humanness. So when we view marriage as something as deeply symbolic and revealing and an opportunity for growth and to be in the highest service of beauty and love, union or marriage or that level of commitment can be very heart-opening for us. It's very difficult for me to say these are the right reasons, these are the wrong reasons. Because again, I can give some overt reasons. very clear, like, you know, should you get married because you have a fear of not having money and your spouse has generational wealth and has a trust fund of$10 million a year and you get access to that and that's why you should get married, but you don't really care for that person.

1:11:31Stefanos Sifandos: Most people would say, no, that's not right. That's wrong. That's not good. But if those people have an agreement and an arrangement and it works for them, I mean, maybe it's not wrong do i think it's nourishing for their souls not necessarily but who am i to judge and i don't know all of the unknown reasons and factors as to why they've got together and i'm not trying to avoid your question here i'll actually directly answer it if in the example of the twins the twin marrying for love i think is sitting in a more advantageous evolved position than the person just saying, oh, well, we've been together seven years, so I should get married.

1:12:10Stefanos Sifandos: Anytime you do anything out of should, you know, obligation, shame, judgment, guilt, you probably shouldn't be doing it, right? But again, who am I to judge? Maybe that time they've spent together, he values so deeply quality time, and he also does have deep care for that person that he wants to marry her. So there's no, what are the right reasons, what are the wrong reasons? We live in such gray and such nuance. But again, like I can give a stack of reasons as to why you probably shouldn't get married if these are the reasons. And they're pretty obvious. I don't even think I'd have to say them.

1:12:48Stefanos Sifandos: I'd put it to your audience now and say, you know, like write in the comments, what are the reasons you think you shouldn't get married? And most of the comments are going to be pretty accurate. It's pretty self-evident, you know, like the example that I gave. But really it comes down to what's happening in here in the person. and again if you can look at marriage as a deeply spiritual union something that carries tremendous meaning especially if you want to bring life and co-create life into this into this earth and this doesn't mean the relationship's going to last forever but if that intention is there and you can you're willing to grow through um that life when that intention is ruptured and challenged and so forth and again that may mean breaking up at some point but maybe not then i think if you're committed to growth and beauty in that moment, you're going to grow and it's going to be a valuable marriage and a valuable commitment.

1:13:45That's such a good answer. That's such a good answer. Especially what I liked about it is the liberty and capacity to self-define what good is for you within your relationship. That's really powerful, but also that sense of obligation. I laughed because I was having lunch with a friend who said, I've been with this person for so long. Do I end it? I was like, sunk cost fallacy is not a good reason to stay in it, bro. You know, I'll give an economic answer to a relationship question. here. So yeah, but again, just giving yourself the liberty and again, empowering people. I love this about you and your work you do.

1:14:27And listen, before you go, I really want to make sure that folks know that you are a resource. You're not just a beautiful mind and a pretty face on an incredible podcast. You have other ways to help people on deeper levels. So let them know about the book, let them know about your programs and how they can get in touch.

1:14:45Stefanos Sifandos: Yeah, of course. Thank you. So firstly, the easiest access point for my work is social media. I really post a lot of content in terms of volume and my perception is it's quality. So I do my best to keep it as quality as possible, but it's a subjective thing. So if you don't think it's quality, it's all good. No offense taken. You're not rejecting me. Maybe sometimes. That's free, right? The next entry point is my book. Very cost effective. They've just released earlier this year with Hay House. You can get it at tunedinandturnedonbook.com. Stack of bonuses there. You can get it through all your retailers like Barnes & Noble, Amazon, etc.

1:15:23Stefanos Sifandos: Through that link. The reason why I direct you to that link, tunedinandturnedonbook.com, is because there's a stack of bonuses there. I also suggest you get the audiobook because in the audiobook, I added a lot more than what I wrote in the book because I filmed or rather recorded the audiobook nearly 12 months after I'd finished writing the book. And I'd grown a fair amount in 12 months. So I just added a stack of stuff to it, which is great. If you want to work with me in a one-on-one capacity, I've been doing this for 25 years, coachwithsteph.com, and that gives you an application. But spend some time on my Instagram, on my YouTube.

1:15:59Stefanos Sifandos: I get to know my work a little more. I've recorded hundreds of podcasts. I've been guests on hundreds of podcasts. Get to know my work a little more before you apply. And I say that because I have a wait list and I don't say that to big note myself in any capacity. I just, I want you to go through a process, a pretty articulate questionnaire and I want you to be confident that we resonate before you apply and not waste your time. But yeah, those are the places you can find me. And for the ladies out there that are looking for deeper love, my wife and I, Christine, run a wonderful program called Be The Queen.

1:16:32Stefanos Sifandos: I will get you the, we're on a wait list at the moment. I'll get you the actual link for that. My apologies, I can't remember off the top of my head, but I'll get it to you so you can put it in the show notes. But we kick that off in October, at the end of October. We're on a wait list right now. We've been running this program for seven years. Tremendous success. There's an in-person component to it as well. That three months live virtual coaching, program design, all those beautiful things, working directly with Christine and I in a container full of amazing women, like-minded, like-hearted.

1:17:00Stefanos Sifandos: Not so much just looking for love, but looking to be greater versions of themselves. And that's where we start. Incredible. stefanos thank you so much brother really appreciate it appreciate you man thank you thanks guys oh man this looks so good man this is so good and for me i was asking questions essentially on behalf of my my single friends who are pissed off you know like i i hear them complaining i was like he has the answers so dude i know you know you're good but sometimes it's good to hear it this was thank you exceptional so good yeah no likewise man i and and it literally like mid podcast remember oh man i've heard crummy before and i fucking love this guy um and i totally didn't make that connection and yeah you're likewise brother you're brilliant i wouldn't and i wouldn't personally say that if you weren't i just um i really respect your work and the way you see things and i love the very grounded approach you have and the very you know not only the intellectual approach you have from the very background that is you, you know, your psychology, law, et cetera.

1:18:06Stefanos Sifandos: But man, just the way you re-explain and explain things and just, you know, very heart-centered and just what an honor to be here with you. I really appreciate that. Thank you. That means a lot. Bless you.

From the publisher

Right now, someone is telling a chatbot about the guy she went on a third date with — and it's giving her a pretty good answer. That should worry you.

Stefanos Sifandos has spent 25 years coaching people through relationships face-to-face, in the room. In this episode, he explains why AI can make you feel self-aware without ever making you change — and why that satiation is quietly keeping people stuck.

We get into:

Why AI relationship advice feels helpful but isn't the same as real growth

Why the avoidant partner always leaves first, and the anxious one won't stop chasing

How to tell if you're doing "the work" or just talking yourself into feeling better

What actually separates self-awareness from real change

Whether sunk cost is ever a good reason to stay in a relationship

What makes a marriage last when love alone isn't enough

If you're in a relationship, thinking about leaving one, or trying to figure out why you keep repeating the same patterns — this conversation is for you.

Connect with Stefanos

stefanossifandos.com

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