Win Valentines Day

Valentine’s day can bring a lot of feelings, one of them I can relate to is…SHAME 

I’m Not a big holiday guy?

Every time, V-day rolled around I would feel shame, maybe you also feel the same thing and say:

  • I’m not good enough
  • I’m Unworthy
  • I’m Unloveable
  • I wasn’t in a relationship when everyone else was

It wasn’t that I wasn’t in a relationship, I was just like NOPE I JUST DON’T DATE

I felt inferior to everyone, I felt like they had figured out something I couldn’t figure out.

It would always create pain, and what I realized was the shame wasn’t from what I thought it was from!

Click below to hear this episode!

Hey! Welcome to today’s episode of the show. Today, it’s going to be all about Valentine’s Day. Oh yes! Valentine’s Day. Now, I don’t know where you’re at, in fact that’s what we are going to discover in today’s episode. What your status is in relationships. Not just whether you’re single or in a relationship, but mentally, what your status is in relationships.

If you’re anything like me, Valentine’s Day can mean a whole lot, or a whole little. You might not care at all, you may not even know that it was Valentine’s Day. Or you might hate it, you might have a charge against it, you might love it. Maybe you love to go buy gifts or chocolates, or receive, or something, I don’t know. So whatever it is, let’s talk about it though because I spent many years of my life feeling shame on Valentine’s Day. So I thought it was important to address because you might relate to this. But I am not a big holiday guy, I don’t really super care about a lot of the main holidays, whether it’s, in the United States, Thanksgiving, Christmas, Fourth of July, I don’t know. I liked to light fireworks when I was a kid. And I liked to get gifts on Christmas, even though our family wasn’t even Christian. We we’re just… American culture man— you by gifts. But in any case, I wasn’t a big holiday guy. I’m not really, to this day. And especially not something like Valentine’s Day where it’s kind of like fabricated by Hallmark. But nonetheless, every time Valentine’s Day would roll around for many years in my life, I would feel shame. The reason I felt shame, a sense of I’m not good enough, I am unworthy, I’m unlovable, was because I wasn’t in a relationship. And not only was I not in a relationship but I was not even close to a relationship. It wasn’t like, “Oh yeah I’m in between relationships right now,” it was like, “No, I just don’t date. I just don’t have relationships.” And so I’d feel really bad about myself. I’d feel inferior to everyone who I thought could somehow figure something out, that I couldn’t figure out. So this holiday ended up causing a lot of pain whenever it came around, especially if someone were to ask me, “Dude, who are you dating?” I’ll be like, “uhhhh…” And I tried all sorts of things, usually just trying to get out of the conversation, or change the subject as quickly as possible. I didn’t like making stuff up because it just felt so bad, felt even worse, so I usually wouldn’t do that, although I tried a few times. It was just overall uncomfortable. But it had nothing to do with Valentine’s Day, did it? It never does. It never has anything to do with the outside thing that we’re pointing fingers at, does it? No, it’s all about me. It’s all about my internal experience of relationship, and specifically my status in relationship. And that’s what I want to explore with you, starting today, in this episode.

By the way, if you’re enjoying this and benefiting a ton from these episodes, that’s awesome, because that’s my point. And if you would like to do me a favor in return, I would much appreciate it. Just go to the iTunes… wherever you found this podcast, and give it a review, because that’s going to help me in my mission to end criticism, fear, self-doubt, social anxiety, and replace it in the world with confidence, boldness, authenticity, power, humor, and love. So I would love that. And your support in my mission there.

So let’s talk about your status. The way I see it, right now as you’re listening to me, you are in one of three categories. Three categories in terms of your relationship status. One, is you’re single. It means you’re not in a relationship. When I say relationship, I mean romantic relationship. It can be with a man, with a woman, same-sex, opposite sex, doesn’t matter.

Category two: You’re in a relationship. That means you’re dating or you are boyfriend/girlfriend, or fiancé, or married, or something in between. Partner, life partner, who knows what. You’re in a relationship.

The third is a bucket catch-all category that’s called, it’s complicated. Who knows what’s going on there. You’re on again, off again, and you’re kind of certain, maybe seeing other people, or this or that and I don’t know. That’s the third category. And you’ll know. You’ll know if you’re there. So what is it? It’s one of those three. And of course we’re going to dig a little deeper because in each of these categories you can have very different mental states that make you either happy or miserable.

So let’s just start with what are the three— one of the three that you’re in. So, identify where you are right now, shouldn’t be too hard. Good. Okay, now let’s look at what are the different mindsets you can have about each of these.

So let’s say you’re single, and you can be in all different emotional states with this, right? You can be eagerly wanting to be with someone, wanting it so bad in your heart, and it’s aching, and you’re pining over the last time you’re in a relationship, and “Oh we shouldn’t have broken up. Oh, I wish I had someone in my life right now, and I want it so bad.”

Or you could be kind of ambivalent about it, “A part of me wants a relationship, but part of me likes being single— I got all my own stuff and I don’t have to answer to anybody.” You’re not quite sure. You kind of want it, you kind of don’t. Part of you wants it, part of you doesn’t.

Or maybe you’re on the other end of the spectrum which is like, “Fuck that.” Maybe you got hurt in a relationship, maybe someone broke up with you, maybe someone cheated on you, maybe something painful happened in your last relationship. Or maybe you’ve never had a relationship and you had some wounding or something where now you’re in a place where it’s like, “Fuck that. I never want that. Relationships are nothing but pain.” Maybe that’s your stance.

So if you’re single, where are you? And if you’re not single, let’s say you’re in a relationship, the last time you were single, where were you? This is important to identify because identifying this is going to help you shift into a state that’s a lot more supportive of getting what you want.

So in a moment we are going to talk about the different mindsets you can have about being in a relationship. Because there are different ways we can be in a relationship. And we will talk about the “it’s complicated” as well. And then let’s look at what it is that you really want, what really works, and how to thrive no matter what space you’re in. Because so many of us have this mentality that if you’re single you got to feel miserable. Or maybe you’re in a relationship and not fully satisfied, and it’s either, “Well this relationship is doomed and I’m going to be miserable as long as I’m in it,” which is not very empowering, or you think that there’s no way to turn it around, or maybe you’re scared to leave it, I don’t know. We’re going to explore that.

The end result of this episode, is you’re going to know where you are now, and then what you need to do to create much more fulfillment in this area. And maybe some old BS toxic stories that you need to let go of. It says, “if you’re single you’re a loser.” I know I had that one for many years. So we’re going to help you shed that, feel way more at peace with where you are. And then you’ll have the courage, and confidence, and the boldness, to go after and create what you want in your relationships, in your dating life. Stay tuned. We’ll be right back, right after this.

So we covered what your mindset might be if you’re single. If you’re in a relationship, there’s a couple of ways it could be going. One, it could be an awesome relationship. You are fully in love with each other. There is honesty, and you’re right there with each other. You know what’s going on with them, they know what’s going on with you. You can share anything with them, and there’s also a level of deep passion, like you’re turned on by each other, you’re excited by each other, you love touching each other, being with each other, making love. That would be what I would call an awesome relationship. There is love, and there’s passion. So maybe you’re experiencing that, and if so, congratulations! Because that doesn’t come by default. It takes work, especially beyond the first couple of months. To be able to sustain that is a sign of you being bold and courageous, because that’s one of the things that it requires to be, to be able to have that in your life. So well done!

Maybe you’re experiencing the second category or the second type of relationship where you are in love. You deeply love each other. Maybe you’ve been partners for months, or years, or decades, and you are deeply in love with each other. You couldn’t imagine living without that person. You guys spend all your time together and have a life together. But there’s not that much energy or juice to it. You guys are like friends, you’re like really good friends. But there’s no passion, there’s no charge, there’s no chemistry, there’s no intimate sexual touching, there’s no fire, there’s no passion. So maybe you’re in that place. That’s where a lot of relationships end up after X number of years goes by. And X is related to the story that the couple has. “Well, that just happens after five years,” “Well, that just happens after you have kids,” “Well, that just happens after 20 years,” right? Some story as to why that “just happens”.

It doesn’t just happen by the way. It’s a result! It’s an effect! Like everything in life is a cause-and-effect. It’s an effect of lack of practicing certain habits. And without those habits, we lose the passion in the relationship. It has nothing to do with bodies changing, with appearances changing. I remember I had a friend, he’s like, “I read a study.” And I love this by the way— I read a study. When people say that in this day and age, it’s as if you’re saying, “I’m about to impart ultimate fact and truth.” Maybe it was back in the day, a thousand years ago with the Bible or something, it’s like, “This is the truth of this particular religion, or the Koran, or whatever.” And now it’s been replaced in our modern scientific materialist culture that’s like, “I read a study. Here is absolute fact.” But the study is like, you just read the headline on Facebook, you didn’t read the study.

Anyway, “I read a study,” that’s what my friend told me: That after two years, or four years, the pheromones change, and the scent of your partner is no longer activating some animal part of you that the pheromones used to. And I was like, “What? What are you talking about?” I think it’s just total bunk, I don’t know what that study was, who knows, maybe they found something, but that’s just another piece of evidence that validates it, that adds energy to this default view of relationships which is highly toxic. Which is what I believed for years. Which is if you’re in a relationship for long enough, you’re going to hate each other. Or at best, you’re going to live together but are not going to be close. You’re not going to be intimate, and you’re certainly not going to be passionate. And that’s what I experienced. My parents, they’re still together, they love each other, they couldn’t live without each other. I don’t see them kiss, ever. I don’t know if they have sex, I don’t know. Doesn’t seem like it. Maybe a conversation I need to have with dad. Or maybe not, I probably won’t. In any case, that’s the default view. I want to challenge that. I want to shatter that. Candace, her smell turns me on like crazy, and we’ve been together five years now. So, I don’t know. Maybe it disappears. Maybe it disappears at year six and a half. In any case, love but no passion, maybe that’s where you are. Unhappy but settled. The third mindset you can be in your relationship. Unhappy but settled. I talked to a ton of clients that are in this place. Unhappy but settled. “Yeah, but it’s not great, but my partner’s critical. But… But… But…” And underneath there is some version of “But this is the best I can do, but it’ll be too hard to leave, but it’s too painful to imagine anything else,” but… but… but… I’m not saying that you need to break up. You got to do whatever is right for you. But I know that’s a major place where a lot of people live. Which is unhappy in the relationship but settled. And maybe you don’t need to break up, maybe you need to radically transform your own life, and magically things will get better in your relationship. Imagine that. I don’t know, it really depends on your situation. Maybe you’re partner’s a dick.

In any case, the fourth category, maybe you’re partner’s a dick, you might want to be planning on this one, which is planning your escape. You’re in a relationship, but man, you’re like in those prisons where those guys have the spoons… this is back in the day, maybe 1930s or something, from what I learned from movies and cartoons. But they would have a spoon and they’d hide the spoon under their pillow or whatever, and then each day they’d crawl somewhere behind their bunk and they’d scoop out a tunnel. They’d be planning their escape for years! And some people are. Maybe you are planning your escape for years. Unhappy but settled. There could be tons of torment there, right? You’re just like, “Maybe I should go, maybe I shouldn’t. I don’t know, I don’t know.” That’s unhappy but settled. Settled makes it sound like you settled to the bottom and you have no feelings about it, but it might be actually very torturous. And same thing with planning your escape, right? Because if you are going to make your escape, you would be done. But planning your escape is kind of that torturous place of like, “Should I do it or not? Okay I got my escape plan. No, no they’re doing better, they didn’t yell at me today.” Whatever. Maybe it’s yelling at you, maybe it’s something else. I don’t know what your dynamic is. But you’re planning your escape. So that’s the other category for relationships.

So, where are you? If you’re in a relationship, or maybe you’re single but when you think about your last relationship, where did it end? How did it end? Or if you’re in a relationship now, what’s your status? Love and passion, awesome relationship, Number 1. Number 2, love but no passion. Number 3, unhappy and settled. And number 4 is planning your escape. So where are you? Be honest. It’s just you and me hanging out. And really, when I say hanging out, I mean you’re just listening to my voice, and thinking in your brains, so you don’t have to tell anyone. I won’t even know! It’s just you. Being honest with you. And that’s one of the most essential criteria for having an extraordinary life, is to be honest with yourself. Even if it’s uncomfortable.

And the last category of relationship is: it’s complicated. And I’m not going to go too deep into this one because there’s so many varieties, and it’s complicated. But some categories could be: Friends with benefits. Someone you sleep with but you’re not quite dating, but it’s not quite fully clear. It could be an on-again off-again relationship, where you guys are sort-of together, and then not, and then seeing someone else, and then back together, and it’s all over the place. Or, something that I experienced is, difficulty and inability to get close to someone. So you date for a little while, and then you breakup, you date for a little while, and then you breakup… I mean with different people. And so, you’re not single, because you are kind of dating. I guess you are sort of single, but you’re not in a relationship, and it’s complicated. I lived that one for three years or four years or something in there, maybe more.

So, now you’ve identified where you are. Now, let me ask you this question. The title of this episode, by the way, I don’t know if I said it in the beginning, is: How To Win Valentine’s Day. So you might be thinking, “What the hell man, how do I win?” Well, let me ask you that question. If you were to win at your relationship/dating life, and that doesn’t mean you have to be in a relationship by the way. Maybe for you right now the best thing is to be single. To feel a sense of autonomy and freedom and self-reliance and exploration and no one judging what you do and you could date someone that you want and you could sleep with someone that you want and you’re totally free and single. And that’s the best thing for you. So I’m not saying: to win is to be in a relationship, or to be married, or something like that. Winning is defined by you… and Charlie Sheen… those are the only people that define winning. But winning… so, what is winning for you in this area of your life? Take a moment and think about that. In this moment right now, what would winning be? Good. Really think about it because it’s important. And then think about what is it that you really want.

So, maybe, winning would be… let’s say you’re single, and you’re desperately wanting to be with someone, and it’s to the point where you’re in pain about it, and also maybe repelling people because you are desperate. Maybe winning would be to relax a little bit, and take care of yourself more, and spend some time with friends, and build your own life so that you are excited about your own life, you’re passionate about your own life. That makes you a hell of a lot more attractive to a potential partner. But your ultimate goal of what you really want might be a deep long-lasting love for life relationship. So winning in the short term might be different than what you ultimately want in the long-term. So I want you to think about both. In the short term, it’s something you could do right now that would help you feel better in your situation, and then, let’s talk about what it is that you really want deep down. Deep down in your plums. What is it that you really want?

And strip away any stories. I didn’t believe it was possible for people to have a relationship. And I had so many relationships where I would start to date them, and then I’d freak out because I had a hard time getting close to people. I had so many relationships like that. And then I heard the story about, “well, if you’re in a relationship long-term anyway, it starts to suck,” that I didn’t think it was possible.

And then I met Candace. She’s my wife and she is amazing. And I was pretty fast in love with her before she knew it. And when we started to actually get close and date, I talked about that fear. That this feels really awesome but basically I have this fear that all relationships lose their energy over time, and basically suck, and then people felt trapped. And she helped me see an alternative, she said, “I don’t see it that way,” and that was really helpful by the way. If she was like, “Yeah you’re right. We’re fucked,” that probably wouldn’t have helped. But she had a very different perspective and she said, “You know I actually think that as time goes on the relationship gets better.” And I was like, “Ooh, tell me more.” She’s says, “You get to know each other more and more, and this person is endlessly fascinating, and endlessly changing, and evolving, and growing, and you get to watch that change and be a part of it, and observe it, and be with them on that journey.” And I loved the sound of that. And I was scared shitless, I didn’t think it could work. I was like, “Okay I hope that’s true, oh my god.” Isn’t it funny how we can cling on to our old beliefs like, “Relationships are all going to turn to shit.” What a terrible belief! Why would I want that belief? But part of me wanted to hold on to it to stay safe. But another part of me, a bigger part of me wanted to take a risk to create what I really want in this life. And I hope you do, too.

So what risk can you take? I’m getting ahead of myself. Before I ask you that question, let me ask you something else. Do you believe you can have whatever it is that you really want? Maybe you want to have an amazing relationship. Maybe you want to have a relationship that’s very honest. Maybe you don’t want a relationship. Maybe you want to be single, and you want to date, and you want to feel totally free and enjoy yourself while dating, instead of feeling afraid and guilty. I know that’s an experience that I had. I had a lot of clients with that, actually. They’ll want to date but then feel so guilty all the time. Like, “Oh I’m talking to two people at once. Oh no. I’m so guilty and bad for doing that.” It’s like, well, did you have agreements with both those people that you’re going to be monogamous and marry them or something? We can feel so guilty, so maybe what you really want is to feel totally free and enjoy yourself. So whatever it is, do you believe that you can have it? If the answer is yes, then good. If the answer is no, then take a look at that. Why would we want to cling on to a story that tells us that what we really want to have, we can never have? Isn’t that a recipe for pain? And yet we do it. And that’s our safety police. And if you don’t know what I mean when I say safety police, you got to get my book, “The Art of Extraordinary Confidence.” I go in super detail into the safety police, who they are, what they do, why they’re in there. So you want to check that out. And you want to shift those beliefs. But, speaking of shifting things, it brings us to our action step.


Action Step

Your action step for today, is a two-parter. Ready? Real quick. 1. Whatever your status is, single, in a relationship, it’s complicated, single and desperate, single and ambivalent, single and I don’t ever want a relationship again, in a relationship and you have love and passion, in a relationship and there’s love but no passion, in a relationship but you’re unhappy and you’re tormented and you’re kind of settling but you’re scared to leave, or in a relationship but you want to get out but you’re scared and you’re planning your escape, or any version of it’s complicated. No matter where you are and what’s happening, don’t judge yourself! Just stop that. That’s the first part of the action step. Just stop judging yourself, because it’s not going to change anything. It’s not going to make anything better, and it’s not going to enhance your relationship situation. Because when you judge yourself, you criticize yourself, you’re abusing yourself. And when you abuse yourself, that does not make you better in relationships. That makes your relationships with yourself and others more toxic. So stop that, let that go. Accept yourself as you are, it’s perfect wherever you are right now, this is where you need to be, to learn to get to the next stage. That’s the first part.

Second part of the action step is to ask yourself this: What risk are you willing to take today, to take one step closer to get to where you really want in your dating and relationship life? Because I spent so many years feeling shame about Valentine’s Day, and “Ugh, I’m not good enough,” and comparing, “He’s got a girlfriend, and all my aunt asks me is why I’m not dating and I feel like a loser.” It’s so low-energy. And you know what it is? It’s cowardice! I don’t say that as an attack on myself, or to belittle or berate that younger version of myself. I say that because people have a confusing idea, that they think cowardice is that you’re scared of something. But that’s not cowardice because everyone gets scared all the time. You’re going to be scared of things for the rest of your life, right? And sometimes people think, you’re scared of something and you’re going to do it, and you’re about to do it, and you stop. That’s a coward. No! That’s actually brave! The bravest thing is obviously go do it, right? But it’s also very brave to move towards and to start to confront that fear, even if you can’t pull it off that time. Cowardice is hiding behind stories and never even testing it. Never even stepping up. Never even questioning and just clinging to those bullshit safe toxic stories like a blanket. Like a warm blanket. No I’m not good enough. Oh, no one could ever like me. And I stay in that place, and I never challenge it, and I never took any risks, and guess what? I never had any success. And the moment, the very week that I started taking risks, I started getting different results. And within a couple months, I was getting totally different responses from women.

So what risk are you willing to take, to take a step towards what you want in your dating life, if you’re single or if you’re in a relationship? Maybe it’s the risk to be more honest. To be more direct. To have that uncomfortable conversation that you’ve been avoiding for weeks, months, or years, that usually starts with a fight, but you don’t stick it out to get to the other side to actually get to know each other better and be closer together as a result. So you’ll find that, what that is for you. That risk.

Bonus tip by the way, the best book on relationships, hands down, you should write this down, you should read it. I think everyone should read, every human should read it, as a precursor, as a prerequisite to having a good relationship, it’s called “After the Honeymoon” by Dan Wile. You should get it and read it. It’s life changing. That’s a bonus action step by the way. Anyway, before we add more actions to the action step, let’s wrap up for today. You’re awesome! Thanks for being with me. Have a fantastic Valentine’s Day. Love the hell out of yourself no matter what situation you’re in. And until we speak again, may you have the courage to be who you are, and to know on a deep level that you’re awesome. Talk to you soon!

Music Credit

All music is licensed or royalty free.

DeepSound – Rain Clouds
(Licensed through

Ask The Shrink:
Boccherini Minuet
(Licensed through

Action Step:
Justin Crosby – Skrillit
(Licensed through

Lokfield – Terra’s Theme Dubstep
(Creative Commons License)

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