Confidence in Dating Is Hard: 2 Ways to Boost Yours Immediately

We’re told all our lives that confidence is the key to everything from our careers to our love lives, but few things can feel more nebulous or fleeting.

Even when we finally achieve the things we thought would give us confidence, it often slips just a little more out of reach.

In today’s video, I’ll show you how to craft a confidence that’s unique to you . . .

Amplify Your Confidence With Me & Charlotte Tilbury.
Register NOW for Your FREE, Live Masterclass on June 9th . . .

Stay until the end of this video, no matter what else you do, because I have something very special to announce at the end of it that I have never, ever done before. And it is going to change the game on your confidence.

Well, we did a video last week and I asked you to leave a comment. I said, “Here’s the comment I’d love you to leave me: What is the thing that you feel is holding you back from being the most confident version of yourself?”

Here’s what you wrote:

“The thing that’s holding me back from being the most confident version of myself is the fact that every relationship that I have had in the last several years, mostly short term, ended with the person leaving me.”

“Chronic health problems. Most guys wouldn’t want to deal with them or have the maturity to embrace me with them.”

“Yesterday, I had a realization my crush may not be as interested in me as I am in him.”

“The thing that makes me insecure is my age. I’m almost in the mid thirties.” (Me too, Stephen.) “And seeing all of the other friends married or have partners in life makes me feel bad for myself and worthless.”

Well, I suppose part of the link between all of these things is that there’s a universality to insecurity, to having our confidence knocked at different stages of our life. I mean, that’s the thing about confidence, isn’t it? You can have had it at one stage. You can relate maybe to a moment in your life where you felt confident and then something happened in your life that knocked you and now you’re trying to get it back. Or maybe you never felt as confident as other people and you’re wondering, “What is this confidence thing people have? What even is confidence?”

Confidence is defined, literally, as a feeling of certainty about the truth of something. And when we look at that idea of certainty . . . I mean, there’s your problem, right? We don’t feel certain about an awful lot in our lives. And that’s why even when our lives appear on the surface to be going right, we can still not feel confident. Confidence itself exists independently of the good and bad things in our lives.

If you don’t consider yourself to be confident in dating, I’ll bet you that that lack of confidence follows you through every stage of the process. Right now, you might be trying to meet someone and you might not feel confident in that. You may be wondering, “Am I ever going to meet someone? I never meet anyone I like. I’m messaging someone on an app. They didn’t message me the last two days. Now I feel rejected.” Or, “It’s never materializing into a date and that’s making me feel like I’m hopeless, that I’m not worthy of a date.”

Maybe you go on a date with an attractive person and you think, “Here we go, I should feel confident now because I’m actually on a date with an attractive person.” Only now a new insecurity creeps in, “I’m not good enough for this person.” Or you look at other pretty people in the restaurant and think, “They’ve got something I haven’t. They’re prettier than me. My date is more busy looking at them than he is looking at me.”

Or maybe you get off of that date and into seeing each other and you think, “Well, I should be confident now, right? We’re seeing each other. We’re regularly sleeping together and having a great time and it seems to be in a good place.” Only now your insecurity is the fact that you’re going into people-pleaser mode and you keep going out of your way to do everything for this person. You see them in their part of town, you see them on their watch, their schedule. You feel like you’re doing everything to make them happy, but they’re not trying as hard. “Am I not worthy of this person trying as hard?” But you don’t say anything because you don’t feel confident enough to ask for what you really want. The lack of confidence follows us to every stage.

What if you get in a relationship with that person? Should feel confident now, right? You’ve got the person. You’re in a relationship. Only now you feel like you’re not good enough to keep you that person. How will I ever hold this person? I’m not good enough for them. Secretly, I know that and they know that. One day they’re going to wake up and they’re going to realize they can get someone better than me. More successful, wittier, funnier, prettier, younger. And that plagues you even within what could, or even should, be a happy relationship.

And so what do we do in order to be more confident? We build up all these stocks in different areas of our lives. We try and fix things, don’t we? Let me get the best body I can because that will make me feel confident. Let me get the best job I can because that will make me feel important. Let me put some money in the bank because that will make me feel confident in my financial security. Let me make myself as pretty as possible because confidence lies on the other side of that. Let me get into a relationship because that will make me finally feel okay. Except in truth, none of these things really work.

If confidence lay on the other side of a great body, a relationship, a great job, then there would be confident people everywhere, but it doesn’t. That’s the first problem with putting our confidence in these things is that they’re volatile. They’re volatile stocks. It’s like building a house on quick sand. You’re only as good as that thing staying the same. The problems with putting our confidence in those stocks is always highlighted when something in life happens to remind us that that thing can change and that we’ve got too much of our self-worth wrapped up in it.

A few weeks ago, I got to stye, really puffed up my eye, made it look a mess. Immediately I was like, “I don’t want to do a video today.” Even this week, I don’t want to do a video. And it was annoying. It was uncomfortable. And it was just this little reminder, “Oh yeah, look. You think you’re confident, but just this little thing can throw you off right now.” That’s a nice reminder and that’s natural. That’s human. It happens to the best of us.

But in that moment, it’s nice little signal to reorient where we’re placing our value, where we’re placing our confidence. Are we placing it in things that can just be taken away from us? Hence why these things don’t work because we’re trying to find certainty in things that are inherently uncertain and changeable.

But the second problem is that even if those things are going well, it still doesn’t guarantee confidence. You know, I was told by a Premiership footballer from decades ago who once won the Golden Boot—meaning they scored the most goals out of any player in the Premiership League that season—he said the next season after winning the Golden Boot . . . you’d think amazing, right? Won the Golden Boot, riding on a high. He said, “The next season was the worst season of my career because I could never live up to that. The best I could do was live up to that. And that was literally the best I could do. More likely is I would fail. I wouldn’t live up to my last season.” So even when we’re winning, that doesn’t guarantee confidence. A lack of confidence or an insecurity follows us to the top. And of course, when we put our value in these stocks, “Am I as pretty as that person? Am I as successful as that person? Am I as intelligent or witty as that person?” When we put our value in these stocks, we start to invite comparison because we compare our stocks with other people’s stocks.

And now we’re in a dating game of top trumps where we’re just a series of playing cards being drawn against each other and you’re always afraid that you’re going to be drawn against someone who’s scoring higher in all of the major categories, money, success, looks, all of these things that we look at and go, “Those are objective measures of how attractive and confident someone should be.”

I remember when I was starting out in my career, I was about 18. I wanted to be great at public speaking, having this thought that Tony Robbins was this incredible public speaker who could captivate thousands of people in an audience at a time. I remember having the insecurity that, “Well, no matter how good I get, I’ll never be as persuasive or as powerful on stage as Tony Robbins because of his sheer physical presence, the height of him, the breadth of him. This is a giant man. Literally I’ll never be that. I’ll never have that no matter how hard I work. And therefore, maybe I’ll never come on the stage the way that he does.”

What’s dangerous about that comparison is we try and emulate somebody else in a way that can have us drifting further and further from our true nature. But what’s more insidious about that kind of comparison is that we end up discounting and often ignoring completely what works about us. Thank God I didn’t get stuck on that thought about not being as tall as Tony Robbins, who is, by the way, because of course the reason that people connect with me is specific to me and to my relationship with people, to something that people connect with in my energy. Dare I say my essence. And I think essence is a very interesting word because have you ever walked past a couple and secretly thought to yourself, “One of the couple seemed a lot more attractive?” And there was that part of you, that terrible part of you that thought, “How did he or she get him or her?”

But the truth is we don’t know the essence of that person that attracted the person next to them. We don’t know what that is. If it were all about the metrics, then you’d look at someone on Instagram who appears to be scoring high in all of the metrics and that would be enough, except you get on a date with someone who scores high in a bunch of metrics and then you just go to yourself, “Something’s off. Something feels off about this person. I don’t know what it is. On paper it should all be right and yet something doesn’t feel right.” Because you didn’t connect to their essence.

And someone can not score high in those categories that we all think we need, but there’s something about their essence. There’s something about the way they are, the way they carry themselves, the outlook they have, the energy they bring that it becomes very compelling about that person. And I think one of the most powerful things we can do in life is get to know more about our essence, get to know more about what works about us. I’m not saying that getting better at things in life is not a worthwhile task. That working on your body, working on your career, getting good at skills, doing things isn’t going to, in some way, improve your life. It certainly can and it can even give you a certain type of confidence. It can give you a kind of localized confidence in an area, a confidence that arises from competence in something.

But that doesn’t mean deeper confidence because of course those things can go away, life changes. And we’ll often find that, that we look at people in life who appear to be very confident and then a change in their circumstances means the complete erosion of their confidence because it’s based on circumstances. It’s not based on something deeper, sturdier, more rooted.

The two pieces of advice that I can impart about this stuff I use from my life is: Number one, since you know empirically from your life that achieving something, getting to a certain metric, getting what you thought you wanted doesn’t change all of your confidence issues, doesn’t eradicate every insecurity, you can almost adopt a bit more of a fatalistic approach to your confidence. Instead of saying, “I’ll be confident when.” Say to yourself, “There’s no guarantee I will be confident when. So if that’s true, I may as well have a bit more of a ‘fuck it’ attitude now.” Instead of waiting for a feeling you’re going to get later, enjoy the feeling now and say, “Listen, I’m going to get better at something because it’s worth getting better at it. I’m going to try and achieve that because there’s benefits in my life from achieving this. But if I know I’m going to feel the same way at the end of it anyway, or if I know that there’s no guarantee that I’ll have eradicated my insecurities by getting there, then I may as well have more of a sense of abandon right now and just say, ‘Screw it. I’m going to enjoy this.'”

And number two, focus on understanding more and paying attention to what your essence is. I know that sounds heady, but to spend time figuring out . . . An easier way of saying it is just, what works about you? What is your special magic as a person? And sometimes the clues are in the kinds of things that the people we love say to us, when we get our best qualities reflected back, or discovering what it is we mean to people and why. I’ve had the benefit of hearing these things in the course of my career, even in the comments. You guys tell me what works about me and why you follow me. And that has been incredibly useful to me because it’s shown me that while I was trying to be good enough in all of these areas over here, my essence was already doing the work over here. All I needed to do was show more of it.

And that’s the really insidious thing about insecurity is that it hides our essence. It stops us from leaning into what already works about us while we’re trying to replicate what works about somebody else. And the most beautiful thing about your essence, about your special magic is that it doesn’t need any of those external wins to exist. For me, my essence is my essence, whether there’s a million people subscribed to my channel or 100. It doesn’t matter how well I’m doing in the score card of life. That thing I take with me everywhere. And it’s about leaning into that as much as possible.

Now, if you’re watching this video and you want to develop this mindset for yourself, because you don’t want to be reliant on things going well in your life for your confidence and you also know it hasn’t worked in the past—no matter how many things you do, you never seem to feel more confident internally, they all just become more and more masks that you wear to hide your insecurities—I have something I want you to be a part of. I have something very special happening on the 9th of June that I would like to invite you to. It won’t cost you a penny, but you just need to sign up. And it’s very special because it’s part of a collaboration and a partnership that is a first for me. I am partnering with Charlotte Tilbury, the world renowned beauty expert, to run a confidence masterclass for her audience and my audience on June the 9th, where we are going to be, over a 90-minute masterclass, breaking down the ways that you can practically be more confident in your life.

Charlotte’s speciality is working on people’s confidence from the outside in and mine is working on people’s confidence from the inside out. And none of this masterclass is going to be about giving you something you don’t have. It’s going to be about taking what you do have, your essence, what works about you, and dialing it up to a whole new level. The nastiest thing about insecurity is that it masks our essence. It has us hiding. It has us in the pursuit and the obsession of things we are not. It has us ignoring the magic that we are, the magic that we have already.

So I’m not giving you that essence here. I’m not giving you that magic. What Charlotte and I are going to be doing with you on the 9th of June is taking what you already have and having you lean into it and double down on that and amplify it for the world to see, because that will be enough.

All you need to do to sign up for this masterclass is go to That’s our initials, When you go there, you’ll have a chance to register. You’ll get an email with all of the details. But like I said, mark your diary right now so that you do not miss this because the people that show up are also going to get a couple of special surprises. So make sure you mark your diary June the 9th and register. If you don’t register, you won’t get the invite. Go to and I will see you along with Charlotte Tilbury on June the 9th. We cannot wait. We’ll see you there.

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5 Replies to “Confidence in Dating Is Hard: 2 Ways to Boost Yours Immediately”

  • I tried booking a spot but i’m getting the message “Sorry, there are no events taking place in the selected date range.” on Charlotte’s website

  • Clicked on the link and the automatic response as “There are no events for this date (June 9)

  • The timing of this video is impeccable, the universe heard me! You speak of confidence or lack of following you at every level. Essence if I understood correctly is what attracts. My situation is, I can interact via text and feel a connection, when meet I don’t feel the “spark”, there is no chemistry. Is it possible my confidence is blocking it?

  • You`re kind. You care. And it is endlessly comforting to listen to You.
    I`m, 50, unemployed, sad and a bit like martini only both – shaken and stirred. I`ve given up the thought of having a relationship, or close friends. I`ll keep up looking for people to think with. Even if it sounds stupid.
    I definitely do some things wrong.
    But just for now – screw it. I like the way I draw.

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