You know those moments where you look back and think, “I wish I’d known then what I know now”? Well, in today’s new video, I share the 7 things I wish I knew back when I was dating. Hopefully you can learn from my mistakes in my 20s and 30s to save yourself extra time (and heartache)!

If you’ve ever found yourself giving more than the other person in your relationship, felt heartbroken that someone doesn’t like you back, or chased the wrong person, you can’t miss this! Watch this video.

Seven things I wish I knew when I was dating. 

I, like many people, perhaps most people, can look back on a time in my life where I was looking for love and misguided in the way I was doing it. 

I want to tell you about seven things that maybe I would in some way go back and tell myself if I had the chance.

Before we get into the video, if you have not pre-ordered the new book, Love Life: How to Raise Your Standards, Find Your Person, and Live Happily (No Matter What), now is an amazing time to do so. Pre-orders really matter to authors like me because they help get the word out about a book.

And I wanted to make it as easy as possible for you to make the decision to pre-order, which, by the way, is getting easier all the time because we’re only a matter of a week-and-a-half out from the publication of the book, and I’ve put together some really exciting things for you.

When you pre-order a copy of the book, you get entered into a prize giveaway. We’re giving away Live Retreat places on my Florida Retreat this year, we’re giving away a 1-on-1 with me, if you’ve ever wanted a coaching session with me privately. We’re giving away some Love Life sweatshirts, and some really cool other things you’ll find at, where you can preorder the book.

You’ll also automatically get an invite to an event I’m doing on May 4 that is an exclusive for book buyers, and a couple of other bonuses. Go to to pre-order your copy now. I can’t wait for you to read this. I’ve worked so hard on it for years now—literally four years of my life—and I just can’t wait for you to get your hands on this. Go to and get yours.

All right, on to the video: What I wish I knew when I was dating.

Number one, you are not for everyone, and that’s okay. I know there were times in my life where if someone I wanted didn’t like me back or went cold, I would take that to be a reflection of my value or how attractive I was, or that I had failed in attracting this person—that I’d made a mistake, that I’d done something stupid that I shouldn’t have. “I shouldn’t have said that; I should have done this.”

But remember this: If we’re being an authentic version of ourselves, we will get rejected. It’s not just normal; it should be expected. Because when we’re bringing all of ourselves to the table, we won’t be for everybody, and that has nothing to do with our worth. It has to do with everybody else’s tastes.

I saw a meme once that said: “You can’t make everyone happy. You are not pizza.” 

Well, so many of us in our love lives try to go around being pizza to people in the world of attraction, but pizza isn’t what we should be trying to be.

When my wife, Audrey, and I go to get sushi, my favorite piece of sushi—the one I look forward to the most—is uni. Now, Audrey can’t stand the idea of uni. It’s not for her. I can’t even get her to have a bit of mine when I eat it. I get so excited about it. I would go to a sushi restaurant just to eat uni. How much Audrey likes uni is not a reflection of uni’s worth. It’s just a reflection of Audrey’s tastes, which, when it comes to uni, are bad. Don’t try to be the pizza of people. Be somebody’s uni, because here’s the thing: Dating and love are not a popularity contest. If you’re being intentional about finding a relationship, you don’t need everyone. You just need one.

Number two, what we want and what we need are very different things. We might get attracted to qualities like status, looks, charm, charisma, the fact that they’re really skilled at certain things, they know five languages, they’re really good at the guitar, whatever it may be. We get attracted to these things that have no bearing on how great of a partner someone will eventually be—about how caring they’ll be in year three, or how much they see us or how loyal or consistent they’ll be.

 None of those qualities that we initially get attracted to are about how happy this person will make us. They might affect how desirable they seem in a room or how popular they are or how much everyone thinks we’re lucky to have a person like that. And that’s, of course, the danger of going after the things we say we want, is that so many of them are driven by our ego that we think we’ll be worthy if we get a person like that. And when our friends or our family validate that by saying, “Oh, good for you, you got a person like this. They’re really impressive. They’re really fun. They’re really charismatic. They’re whatever. They’re good-looking.” When we hear those things, we think, “Oh, they must be great. They must be worth holding on to—even the people around me think they’re wonderful.” But so often, that divorces us from our real experience of being with someone. When we’re so busy trying to “get” someone or hold on to someone, we stop paying attention to how we actually feel when we’re with them. 

I know I’ve been in a situation before where I was so busy trying to just hold on that I didn’t actually notice that I was utterly miserable by being there. And when we notice that, when we start paying attention to our actual feelings, and we realize we’re unhappy, we realize how absurd it is to keep wanting someone who is making us unhappy.

So it’s okay to want certain things, but never at the expense of what actually makes you happy in a relationship. Question the things you’ve told yourself you want. Get in touch with the things you actually need.

Number three, “hard to get” does not mean “great to keep.” There is this strange economics of value that happens for many of us where if someone’s scarce, if they pull away, if they make us have to work really hard for their attention, or if they’re unavailable, we feel like they must be more valuable, but one does not necessarily lead to the other.

There are plenty of reasons why someone is not available to us that have nothing to do with their value for us. I know there were times in my life where I thought someone was more valuable because I couldn’t get them, and that made me think about them and ruminate about them in ways that were unhealthy, and attach a level of value that they’d never even earned, and I didn’t know they had.

So just because someone is hard to get, it doesn’t mean they would be very valuable for our life if we were able to get them. And by the way, hands up in the comments if you’ve ever thought someone was hard to get, and then you got them and realized you didn’t want to keep them.

Also, remember this, because I can flip this as well: Your “sure thing,” the person who wants you, is somebody else’s unrequited love and certainly has been in the past. This realization for me meant that when Audrey—my now-wife—came into my life and presented as healthy love, presented as someone who actually wanted me, someone who was being intentional and wanting to move things forward with me, I didn’t devalue her because she was presenting as easy and not challenging in that way of me having to chase and chase and chase. Instead, I was able to see that this person was incredible for me, and she just happened to be, lucky for me, at a point in her life where she was ready for something more.

Just because someone is presenting as safe and secure for you doesn’t mean that they’re less valuable, and it doesn’t mean they haven’t at a different point in their life been somebody else’s “hard to get.” Instead of devaluing the person who actually wants you, see yourself as lucky that their “hard to get” isn’t what you’re experiencing.

Number four, intention is everything. Intention is: Does someone want the same things I do? Are we on the same path? Do we see what we want to build? Do we both want to be in a relationship? Do we want to be in a relationship with each other? Is what I want for my future the same thing they want for their future? Or at the very least, are our futures compatible? This is intention.


So often, people ask me, “Matthew, do they like me? Do you think based on what they’re doing, they like me? They watch my Stories. Does that mean they like me? They keep texting me, or every time I text them, they text me back. Once a month, they ask me on a date. Surely they like me. Why else would they be doing these things?”

There are so many people who go on a discovery to try to figure out if someone likes them as if that’s the most important question. The answer to that can be frustratingly simple, which is: “Yeah, they like you. If they keep wanting to have sex with you, if they keep wanting to spend time with you, if they keep giving you their attention, on some level, they like you.”

That doesn’t mean anything. The fact that someone likes us might be enough for them to give us some of their attention sometimes, but it doesn’t mean they have any value for our future, because in order to have value for our future, someone actually has to want the same things we do. They have to want to be with us. They have to want to say “yes” to a relationship with us. If someone’s not in the same place as us and they don’t actually want anything more than some hits of attention or to share our company for a few hours a week or a month, or to just exchange messages, then how relevant is it that they like us?

It doesn’t matter. What matters is what they want to pursue with us. So we have to stop asking ourselves if someone likes us. I always remember one of my first-ever YouTube videos, when I was, like, 19 years old, about how to tell if a person likes you. But in the years that followed, I’ve made far more videos about whether someone has any real intentions with you, because someone liking us can be really uninteresting if we find out they don’t actually want what we want. Intention is everything.

Number five, get out of the middle. This is something I would have told myself looking back, because in times where I could have been way, way happier by being decisive, I created a tremendous amount of unhappiness for myself and for other people by getting stuck in the middle. And here’s what I mean by that: There was a kind of tendency for me to overthink.

My overthinking had me be incredibly indecisive about what was right for my love life and who was right for my love life and who should I ultimately end up with. Like many people out there watching this, that decision overwhelmed me: “This is probably the most important decision I’ll ever make. How do I ensure I make the right one?”

And when I was overthinking about that, instead of just being in the moment and experiencing someone, and seeing where something went, it would make me look for things that made someone not the right person.

 If I found something that made someone appear in some way—big or small—to not be the right person, I would then withdraw, but I wouldn’t withdraw in the sense that I would end it and move on. I would then kind of keep the relationship at that level without progression. And of course, this is exactly the pattern so many people do that ends up hurting somebody else so much, because you can waste an extraordinary amount of someone’s time and really hurt them by staying in the middle instead of either saying goodbye or fully committing. But I found myself doing this in my own love life. 

The shame of it was, by staying and living in my uncertainty and not progressing the relationship, I also never gave that relationship the chance to be what it could really be. Because you never know what a relationship can be if you don’t go all-in.

You never give it a chance to really flower into the thing it could be. You certainly never give the other person the chance to be all they can be, because if someone feels inherently unsafe or insecure or can sense that you’re not all-in, they don’t feel safe to really open up or be themselves or give the kind of love they can give when they are feeling safe.

I neither freed up space for something that was right nor got to see if the person in front of me and the relationship in front of me could be right. I just stayed in the middle and spent an incredible amount of time and energy and emotions in that place. And of course, me living on that level with someone didn’t avoid the heartbreak I was worried about by getting too invested, because it ended up in heartbreak anyway for everyone involved, so that’s what I would have told myself: “Get out of the middle.”

Number six: Never abandon yourself for someone you want.

It is such a natural instinct when we want someone, when we want to please someone, when we want to make them happy . . . to start to ignore things we need: friendships, hobbies, aspects of our work that are really important to us. Interests we have that we would ordinarily give time to or want to talk about.

We start to morph our world into one that suits them so we can make them happy or appease them. We’ll just make ourselves convenient for their needs and for the ways they want to spend their time, or the projects that are important to them—their sense of purpose in life, of how they want to live, and it can feel like we’re doing a good thing when we do this.

 It can feel like we’re being incredibly sacrificial in the best possible way—that we’re making the compromises people do when they love someone. The danger, of course, is that we start to forget or not pay attention to the fact that every compromise, every sacrifice, is always in the same direction. It’s always you giving up something that’s important to you or something that makes your life your life in service of somebody else. And maybe that’s okay for a little bit of time when you’re in a certain chapter with someone. But when that chapter never ends, we can lose track. We can start to forget ourselves—we can start to forget who we are and what we enjoy.

And we can ignore the fact that all of these things we’re doing for this person are completely taken for granted. They’re not connecting to the sacrifices we’re making. They’re not connecting to the ways we’re going out of our way for them. It just becomes an expectation, and that’s why in certain situations, when we start trying to reclaim ourselves or rebuild our lives, we can suddenly realize that that person won’t make any of the same sacrifices in return. That person’s not willing to compromise. Now all we’re doing is trying to take away something that has become an expectation. So we have to be really careful not to abandon ourselves.

The right relationship is the one where we can be ourselves with our interests and the things we love about our life and the people in our lives, and we can merge those with somebody else’s. Not one where we have to abandon ourselves and our world in order to keep the relationship going. 

Number seven: Just because it’s right doesn’t mean it will be easy. 

There is a line that’s thrown around, which is: “If it’s right, it’ll be easy.” And I don’t always agree with that. I think it will be easy a lot of the time, but there will still be hard moments, even in the right relationship.

There will be collisions, there’ll be tension, there’ll be disagreements, there’ll be times where someone innocently activates our trauma, our wounds, our insecurities, the baggage we’ve brought to the relationship, and it doesn’t necessarily mean they’ve done anything wrong, but it will be hard for us that we feel triggered by something they’ve done.

I know that in my dating life, a lot of the time when it got hard, I would push someone away. I would become avoidant. That was because I was scared. This person hadn’t done anything wrong. I just got scared and started to push them away. The danger with that idea of “When it’s right it’s easy,” is that often what feels easy to us is what’s comfortable to us. What’s familiar to us.

I know for a long time in my relationships, what was really comfortable for me was being in the driver’s seat, being the one in control, but that wasn’t necessarily what created an equal relationship. It wasn’t what created happiness in a long-term relationship. It just allowed me to feel like it was easy for me, but easy isn’t the same thing as fulfilling. So I got to a point in my life where I realized: “I’m going to have to start to embrace what is uncomfortable to me.”

And I took that a little far as well. Because when the pendulum swung all the way in the other direction, I got really hurt, because when it got hard, I said, “This is good medicine for me. I’m going to learn. I’m going to improve. I’m going to grow in ways I need to grow.” 

But what I didn’t pay attention to was that it didn’t get any easier. It just stayed hard, and in some cases, it got worse. So it’s also not true that great relationships are just hard. The nuance is somewhere in the middle, and that’s something I had to learn the hard way: that it’s okay for something to be hard in moments. That doesn’t mean it’s the wrong relationship.

If you’re able to embrace the hard and resolve it together, in the right relationship, hard leads to easy. In other words, if I would get triggered by something, and I brought it up and we had a conversation about it, there may be an initial tension or argument or blowup. But the way we came together afterward, in a compassionate and kind way, allowed me to heal that.

It was a corrective experience for me. And at the end of it all, I actually felt much, much safer, and in many cases, what’s been amazing about my marriage is that triggers I once had are no longer triggers in the same way, because the way we’ve overcome them has actually allowed me to heal and feel safe in ways I never had before. But I never would have gotten to that if I’d just bailed as soon as it got hard. So what I wish I knew when I was dating was that it’s okay for something to be hard, but it should never stay hard. Hard should lead to easy.

Thank you for watching the video. Grab a copy of your book at Before you go, leave me a comment letting me know what you thought of this video, and don’t forget to like and subscribe to the channel so that next week you get the next video automatically.

Thank you so much to everyone who has been pre-ordering a copy of the book. I cannot tell you how much it means to me, and the more of you who do that, the bigger a splash we make in week one, and the more we make a splash, the more people who need this book will hear about it. So help me raise the standards of not just you and the people you love, but all the strangers out there who need to hear about this book to make great decisions in their love life and do love better. I’ll see you next time.


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