The #1 Reason You Feel Powerless in Dating (and How to Fix It) | Matt Monday
1 Sept 2025 · 30 min
In this episode Matthew AI delivers a deep dive into Alfred Adler’s psychology and its implications for modern dating, interwoven with several commercial breaks. He begins by promoting Sleep Number smart beds and Mint Mobile, then shifts to a detailed analysis of the book The Courage to Be Disliked (Ichiro Kishimi & Fumitake Koga). Matthew argues that trauma does not dictate one’s future; instead, present‑time goals shape how past experiences are interpreted. He illustrates this with a story of a shy woman whose blushing is an excuse for a hidden goal of avoiding rejection. He then distinguishes Adler’s concepts of trust (conditional, earned) and confidence (unconditional belief in others’ innate goodness), explaining how confidence is essential on first dates. Next, he explores three further Adlerian principles: 1. Courage to be normal – rejecting the cultural pressure to be special and embracing self‑acceptance; 2. Life is not a competition – viewing relationships on a horizontal, equal “football field” rather than a vertical hierarchy; 3. Date as if you’re dancing – focusing on the present, enjoying the process rather than obsessing over outcomes. Throughout, Matthew ties each principle to practical dating advice and highlights how loss of confidence fuels current dating struggles. He concludes by inviting listeners to a free live training called the Love Life Reset (mid‑September), aimed at both singles and partnered people, promising a fresh mindset to break dating burnout. The episode ends with additional ad spots for Thrive Cosmetics (vegan fall makeup) and HeroBread (low‑carb breads).
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I want to tell you about a book I discovered recently that has nothing to do with dating, but has changed how I think about dating in five key ways. Some of these ways are upsetting, but kind of in the best way. Others are controversial, so they're going to have to come with a giant disclaimer. But all of them are fascinating and I suspect will radically change the way you date moving forward. The the book I am talking about today is the Courage to Be Disliked by Ichiro Kashimi and Fumitake Koga. This is a book between a young person and a wise older philosopher who is trying to teach the young person the methods and the theories of Alfred Adler, the psychologist who was around during Freud's time and Jung's time but had wildly different opinions. In some cases they diametrically opposed opinions to Freud. And this is where so much of the controversy comes in. Because the first big thing from this book that struck me was this idea that your trauma does not shape your life, your goals do. In fact, the book goes as far as to say that trauma doesn't exist. Now again, I want to repeat this very clearly so that you understand my position on this. I believe that trauma is real, very real, that it exists, that it absolutely has a profound effect on people's lives. But where I find Adler's stance helpful is in my own life, looking at where has my Trauma become a way to avoid something that would actually make my life better if I had the courage to approach it. And you might ask the same question in your own life. If you've come out of an abusive or narcissistic relationship, for example, you can look backwards at all of the ways that that has shaped your ability to trust other people. But what you can also do is decide a goal that you believe is going to serve you today. What Adler would have said is that when we have a different goal, we will choose to focus on different parts of the past. That's what he meant when he our past doesn't determine the present. Your present determines the past. Because when you have a new goal in the present, you might start looking for different examples in your past. In that example, the person who's been with a narcissistic person might say, instead of focusing all of my attention on all of the ways that I was wronged by that narcissistic person in the past, I might put my attention on the people in my past who were there for me. The people I could trust, the people who didn't gaslight, the people who were people of their word. And the reason I would do that is because I now need evidence to support a different goal. If my goal is avoiding rejection or never getting hurt again, or never being in a dangerous situation again, then I will focus on the trauma in my past that allows me to achieve the goal of never putting myself out there again so I never face those situations again. There is one example in the book of a young woman who can't talk to a guy that she has a crush on because she keeps blushing every time she goes to talk to him. And so she goes for help, and she says, it's such a pain. I really like this guy. I'd really like to be able to approach him and speak to him, but I just can't because of the whole blushing thing. Now, the philosopher's approach when he talks about Alfred Adler's concepts in relation to this is to say that the girl wasn't not talking to the guy because she was blushing. She was blushing as an excuse not to talk to the guy. Because her real goal was to not get rejected, to not talk to him. Because if she could avoid talking to this person, then she would never have to burst her bubble of the idea that if she just did talk to him, something might happen. She wouldn't necessarily consciously be aware that there's this hidden goal of maintaining the story that something could happen with this guy. But once you look at it through the lens of my goals are determining my results in the present. You can't unknow that. That makes me think about what hidden goals I'm constantly trying to achieve in my life, but I'm blaming on my past. I wonder if it's the same for you too, if it is, and as you're thinking about this, you're having a mini revelation about a hidden goal you've been achieving and using your past to achie that goal. Let me know in the comments. I would love to know. While we're all together in this moment, I wanted to take the opportunity to tell you about something I have coming up in the middle of September. It is called the Love Life Reset. I work with people year in, year out who I know in my bones can find the love that they're looking for, but have kind of become stuck. They've become stuck because dating can suck really, really bad. They've become stuck because they keep getting the same results over and over and over again, and that creates its own kind of anguish and disillusionment with the process. It feels like we can't keep up our resilience anymore in just working through the rejections or all the times when we're trying with someone but they're not putting in any effort. We can get stuck because we've just lost the belief that this is going to happen for us. But what I am fascinated by and excited by, and I find to be a very empowering thought, is that we can actually adopt a fresh way of being in this area of our life and a new mindset that can radically change the results that are available to us. And that's what I'm going to be doing with you in the middle of September on this free live training called the Love Life Reset. I'm going to be spending time with you, giving you a completely fresh approach to your love life. Even if you feel like you've been banging your head against the wall, nothing's been working. You've. You're sick and tired of it. Maybe you even feel close to dating burnout. You really do want to find love, but you feel like I just can't take more rejection or more disappointment or more people who just aren't even trying. You know, it can feel like it's hard to get someone to go on a real date, let alone commit to an actual relationship. But I know that when we step outside of that frustration that we've gotten locked into because we get very tense in this area of our life after a while, especially when it's not been going the way we want, if we can step out of that and into a completely fresh approach, calm approach, an empowered approach, where we can take control again, things change. And they can change quicker than you'd ever imagine. So this is my formal invitation for you to come and join me on this free event that I have put together called the Love Life Reset. It's happening in mid September. It is my last big event of this kind for the entire year, so please don't miss it. I promise you it's going to send you into the last quarter of this year with a completely different level of energy and hope and excitement for your love life. I also want to say that for people who are already in relationships who are watching this, the Love Life preset is for you too. I didn't design this one just to be for people finding love. I also designed it for people who have maybe lost their sense of calm in love or who are struggling in various ways in their relationship. Maybe you're struggling with old patterns of jealousy or anxiety or people pleasing. Maybe you're questioning your own worth. Maybe you're finding it hard to stand up yourself. I am going to be working with you too. So please don't think this is just for single people. If you're in a relationship, the Love Life Reset is for you too. I'll leave a link below. It's lovelifereset.com. click the link and you can join me and get signed up right now and then I will see you in mid September. All right, back to the video. Here's the second crazy thing that Adler said that we have to have an unconditional belief and acceptance of others, regardless of their actions or whether they are trustworthy. That sounds like a recipe for getting absolutely destroyed when it comes to our love lives. I know this because I have talked about this for the last 17 years of my life. We encounter all sorts of really problematic behavior in dating. People who gaslight us, people who love bomb us, people who mislead us as to their intentions, people who lead us on and hook up and then never call again. There's all sorts of ways that having an unconditional belief in other people, regardless of how trustworthy they are, could bite us. However, there is a way that Adler talks about this, that the more he talks about it, the more it starts to make sense, because he actually makes a crucial distinction between what he calls trust and what he calls confidence. Let me explain. Trust, in Adler's definition is conditional. Trust is what a bank has when you ask for a mortgage and the bank says, I need a property or an asset in order to secure that mortgage. So that I know no matter what happens, if you default on, I can take that asset and get our money back. That's the kind of trust that Adler is talking about. Confidence is what Adler was talking about when he said we have to have an unconditional belief in other people. And there he was talking about a much more general kind of generous interpretation of the actions of human beings. A belief in the innate goodness of people that most people who do bad things aren't trying to do bad things. They're trying to get a sense of significance or what he called superiority. And that generally speaking, if we want to have healthy, productive relationships in our society or community, then we must have confidence in other people. Now, I found this distinction between trust and confidence very helpful because trust is something that is earned right over time. What's the. What's our version in dating of the collateral the bank takes when you're getting a mortgage? Our version of it is people's dependency over time, their reliability, their sticking to their word.
They.
The fact that they continue to show up for us and be who they say they are. Trust gets built through all of those little actions that eventually lead to us having a conditional kind of trust. I trust you in this marriage because of the history we have. I trust that you won't hurt me because of everything that we've been through and you've shown me who you are every stage of the way. But confidence in the Adlerian sense is what we need when we show up on a first date. Confidence is the ability to see the other person in front of you and say, I'm going to assume the goodness in you. I'm going to assume the best. I am going to have a generosity of spirit about who you are. Which is the phrase that my wife always used when she was talking about how we should be with people, have generosity of spirituality, spirit. But I would say that out what we call generosity of spirit is what Adler defines as confidence in other people. Now, some of us struggle with that idea of generosity of spirit, Especially if we have been knocked one too many times or we've dealt with nasty people in the past that has really knocked our faith in humanity. How do we get back that confidence that we can extend universally to humankind that allows us to be that way on a date? Well, I believe that if we fundamentally know that we are good and that that doesn't stop us from Having bad days doesn't stop us from having selfish moments. Doesn't even sometimes stop us from doing bad things. If we know that we're fundamentally good and yet we can be imperfect in all of those ways, then we can assume it's the same for other people too. That most people in this world are people who are generally good.
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But are imperfect and the influences and the world they're around affects their ability to bring out their kindest, best, most unselfish self versus their worst self, the kind of self that could hurt us. Once we have this kind of confidence in other people, it makes us more attractive because now the other person showing up on a date with a sense of optimism, with a sense of radiating as someone who sees the goodness in other people and what Adler says is if we want other people to believe in us, if we want them to have confidence in us, we have to be willing to have confidence in them. I truly believe one of the reasons so many people are struggling in dating right now is because they have lost the confidence that they used to have in the goodness of people. The third thing that Alfred Adler said that might be the most difficult one of all of these to actually put into practice and is that we must have the courage to be normal. Now this seems like a revolutionary idea in a world where everybody has an Instagram profile that is a shrine to themselves and their attributes and their life. We are living in a world where attention seeking is rife. And it's not only rife, but is constantly rewarded with followers and dopamine and sponsorship deals. We are living in a world where everyone, it seems, is trying to stand out and be special in their own special way. So the courage to be normal in a world like this can be seen as a radical act, as a quiet rebellion. And as Adler puts it, why is it necessary for us to be special? Probably because one cannot accept one's normal self. And it is precisely for this reason, Adler points out, that we try to be good so that we can get praise for doing good things and impressive things. And when we fail at getting praise in those ways, many people turn to being especially bad. Because being bad and standing out for how bad we are can also be a way of achieving some form of superiority and attention. And of course, it's so natural to try and find ways to be special in dating, especially in what feels like an ultra competitive dating market. We all have our ways of trying to stand out. I coach a lot of guys who will tell me, Matt, I, I, I keep attracting people who only want me for my money. And I know deep down that that's often because they are trying to be special by leading with the fact that they have money. Whether it's by what they wear, what they drive, what they talk about on a date, or the fact that in a first date scenario they have taken someone to a five star restaurant. When we lead with that, we're going to attract people who want us for that. So we have to be wary of the ways that we try to achieve specialness because they can actually be hurting us. In a scenario like that, that guy with money might have to stop leading with his money if he wants to attract a different kind of person. That's tough for that person. It requires courage, it requires risking blending into what we see as the faceless normal masses. The desire to be special also affects who we choose. Because when we're trying to be special, we don't just try to appear special to the person we're dating. We try to date someone who is special, who by being with them, we think raises our value to everybody else. So we go out looking for someone special. A specialness that is usually defined by someone's level of looks or power or charisma. This is another way of looking for validation through another person. So the crucial first step in the courage to be normal is self acceptance. As Eric Frum put it, respect for another human being. Is the ability to see a person as they are and the placing of worth on that person for being that person. And this is what we can do for ourselves, too. We can have regard for the person that we are, as it's put in the courage to be disliked. You are just fine as just you. There is no need to be special. There is value in you just being you. Now, by the way, that doesn't mean that you can't stand out in your own way. But let's talk about that concept itself and how we get standing out wrong. 4. Dating is not a competition. Now, Adler didn't say dating is not competition, but what he did say is life isn't a competition. That we shouldn't be competing with each other. Because when we compete with each other, we create enemies, not comrades. And he believed that the key to a healthy society and a community is people having each other as comrades, seeing each other through the lens of friendship, not seeing each other through the lens of competition, that is enemies. And the way he talked about things not being a competition is that we shouldn't go through our lives feeling inferior to other people or wanting to be superior to other people, because that's what creates the element of competition. We don't feel good enough. We feel inferior. And what Adler said was the reason we feel inferior and we obsess over being superior is because we see relationships as vertical. We see people as either being above us or beneath us, when in fact we should see relationships as being horizontal. That we each have our strengths and weaknesses, the things that we're really good at, the things that make us stand out, the things that trouble us. And the way he represented that was through the idea of us all being on a football field together. And we're all in our own race. And some people are ahead, some people are behind, some people are running faster, some people are running side by side. We're all different and have different attributes on the field, but the field is level. We're all standing at exactly the same level. We are all different, but we are equal. And when we see life that way, we realize that we are never comparing ourselves to somebody else. What we are doing is comparing ourselves with our ideal self. And when we see someone who has more than us or is able to do or achieve or be more than we ever will be able to, we can still see them as a comrade, we can still see them as a friend, because we're all equal on the same field. I think this has massive implications for dating. Because one of the things that Makes us feel inferior in dating is this feeling that we don't match up to what we see out there. So we go into a date and we feel not good enough. We look at someone and we think they're intimidating because of the way they look or their style or what they've achieved in their life or the speed of their wit. And we think, God, I can't match up to this person. But if we see them as being on a level playing field with us where we're different but equal, we can simply celebrate those aspects of them. The same is true in a relationship. Someone else's success in a relationship doesn't diminish our worth. We can be with someone who is incredibly impressive in all sorts of ways and simply celebrate them knowing it takes nothing away from our inherent value. Now, I am not saying it's easy to practice not seeing life and dating through the lens of competition. It's not. Although I do think the football field analogy really helps. But it is made easier by the next concept, which is not only wildly counterintuitive, but some would say goes against everything they have ever been taught. Number five. Date as if you're dancing. Let's imagine the way that most of us go about our love lives, which is that everything we do to find love, to go on an app, text someone, go on dates, put ourselves out there is all a means to an end. It's all about getting to that destination of having found the love of my life. And what Adler would have said is that the destination is not the most important part. The most important part is all of the little moments along the way where you are experiencing life. He talks about it in terms of mountain climbing. You know, if you value climbing, then you won't think that if you set out to climb to the mountaintop and you didn't reach it, that the whole expedition was a failure and was pointless. That regardless of whether you reach the top, an expedition took place, climbing had to happen, and the point was the climbing. We have this constant focus on the future and how likely it looks that we're going to reach the point that we want to reach in the future. How likely it looks that it's ever going to happen for us. And if we conclude that it's, you know, it's hard or it's never going to happen, then we can become dissuaded from fully experiencing and living life. Now, that's how it is with dancing, right? We're not dancing to get somewhere when we dance. We're dancing because we're enjoying the act of dancing. Now, in the course of dancing, we will end up in a different part of the floor. Our feet will end up on a different part of where we are. Because as we dance, we move. And so it is with life. As we live life, we move, we end up in a different place. But it wasn't that we said it was only worth dancing if we ended up in a different place. It was worth dancing for the act itself. And I actually think that dating, or let's say, forget dating, dating is such a loaded word, and it has so many negative connotations for people. But the act of finding love or being open to love, I think can be seen in the energia sense, not as a kinetic journey from A to B, but a way of being dancing. If you see dating as simply exchanging messages on a dating app or being on a crummy first date, then it's going to be hard to see it in that sense. But if you see the act of living in such a way that you could invite love into your life as dancing, I think that's possible. The idea that my ability to leave my house not knowing what's going to happen today, or to remain open, armed to people in this world and the possibilities that people bring with them every time I meet a new person or choose to flirt a little or play a little, or be a version of myself that creates energy in this life or to expand my life by joining a club or a class or some new activity that I wanted to try anyway. There is something about living in such a way that can invite love into our lives that is like dancing and certainly will be worth it for its own sake. Energia, not Kinesis when it comes to our dating lives, dating is dancing. And this idea from Kashimi might help sum a lot of this up. He talks about this idea that when we're so focused on the past and our story of why it's so hard for us in the present, let's say, to find love, and we're constantly focused on a future where we're scared our ultimate goal won't materialize, won't be realized. It's as if we are standing on the edge of a stage in a theater with the house lights turned down. And when the house lights are turned down, you can see all around you. You can see all the way to the back of the crowd. But when we shine a bright light on the present, when you turn up the house lights, all of a sudden you can't even see the first row. When the lights are turned up in our lives, we can't see the past or the future. There is only now, and there is such a power in that that we're no longer attached to our story that limits us. We've let that go, and we're not constantly fretting about whether or not something's going to happen in the future. The lights are up and we are dancing and experiencing life fully in the present. If you would like me to do more videos of this kind where I take take Adlerian psychology or other forms of psychology and apply them to dating, let me know. Or was it just too heady and you want me to get back to giving flirting tips? Leave me a comment, let me know. And don't forget to sign up to the Love life reset@lovelife reset.com and I will see you for that big live event in mid September.
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