How To Cultivate Bravery In Your Dating Life [EP038]

You can truly and powerfully change your dating “luck” by adding conscious moments of micro-bravery into your search for love. In this inspiring episode, you’ll learn exactly how to cultivate bravery in your dating life.

Episode Table of Contents

Episode Introduction: Cultivate Bravery

Cultivate Bravery

You can transform your search for love. Truly change your luck by adding conscious moments of micro bravery into your life, both online and offline. Stay tuned to the Deeper Dating Podcast to learn how.

Hello, everybody, and welcome to the Deeper Dating podcast. I’m Ken Page, and I’m a psychotherapist and the author of the bestselling book Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy.

Today, I’m going to talk about the power of bravery in your search for love and how small steps of micro bravery can change your present and change your future in powerful and inspiring ways.

Every week on the Deeper Dating podcast, I’m going to share the greatest tools I know culled from science, psychology, and spirituality to help you find love and keep it flourishing and heal your life in the process. Because the skills of dating are nothing more than the skills of love, and the skills of love are the greatest skills of all for a happy life.

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Adding a Touch of Bravery

A touch of bravery
Photographer: Joshua Sukoff | Source: Unsplash

Gandhi once said, and I love this quote, he said,

“Love is the prerogative of the brave.”

And damn that is true. But dating is also really the prerogative of the brave. And that’s what I’m going to talk about today. Dating can be so hard, and it can be so repetitive, and so boring, and so frustrating at different points.

One of the greatest ways that you can keep your search for love and your dating life fresh and to kind of keep hope alive is by growing and feeling that you’re growing and changing what you do. One of the best ways to do that is to add a touch of bravery to your search for love.

God knows every one of you is brave by listening to this podcast and wanting to grow. By being out there looking for love, it’s exquisitely and existentially brave right there on its own. And other acts of infusion of micro bravery will feel wonderful. They will make you feel invigorated. They will open new doors of thinking for you, and they’ll let you achieve new results for you as well. That’s what we’re going to be talking about today in a lot of different ways. It’s a super exciting subject for me.

Here’s another benefit that you’re going to get from infusing moments of bravery and actions of bravery into your dating life. There is a fascinating connection between Eros, your erotic self, your romantic self, your erotic nature, that feeling of your blood kind of boiling and the kind of beautiful fruits of the earth, and sex, and love, and romance, and all those things. There’s a connection between that and getting brave. There’s a connection between that and fear.

An Edge of Novelty

Research shows that when you bring an edge of novelty, fear, and risk into your life, your erotic self gets stronger. You’re more likely to ask people out on dates. You’re more likely to have sexual and romantic fantasies. You feel more alive, you feel more engaged in life. So those are some of the benefits of what you’re going to be learning today by infusing more bravery or different kinds of bravery into your dating life.

I want to say one more thing about another benefit that’s kind of a hard-to-put-into-words one, but a rich and powerful one. If you think about the concept of an initiation rite, something that’s done in so many different cultures. An initiation rite is where you’re in a situation where you have to do something scary and hard that you kind of don’t know if you can really do. But then you do it, and you come out the other end more yourself.

There’s a way when we commit acts of bravery that on the other side of that we come to know ourselves.

We come to sense, know, taste, and feel the person we’re meant to be. And maybe that’s the most spectacular gift of bravery of all. These are some of the benefits that you’re going to be receiving by taking some of the actions that we’re going to talk about today.

So you know, in my classes, courses, and in my book, the process goes like this: The first step is kind of learning self-honoring, learning to discover your core gifts, the parts that are the most essentially you that maybe you feel vulnerable about sharing with the world. Maybe you feel shame or insecurity around them, but on some level you know that they are precious parts of you.

The Stages of the Journey

The first stage of the journey is learning to honor, and dignify, and treasure those authentic parts of you. The second stage is looking. It’s learning discrimination. It’s learning to look for people who also honor those qualities in you. There’s a fascinating formula that I kind of think of as the deeper physics of dating, and it’s this:

The degree to which you treasure, not just accept but treasure, these core gifts in yourself to that degree, you’re going to find yourself sexually and romantically attracted to people who are good for you.

Amazing and true. And you’ll find yourself somehow meeting them more. It’s an amazing thing, but it really, really does happen. Anyway, in my courses, those are kind of the first two stages. And for all of you who have done work on yourself, this work that I’m describing, what you can learn about through my book and elsewhere, or any other kind of personal growth work that you’ve done learning to dignify and honor your authentic self, to the degree that you’ve done that, you are shifting the field somehow in your dating life. You’re shifting kind of your own. The nature of your own magnetism, who you’re drawn to, and who you draw, who you’re attracted to.

So at a certain point, it’s time to get out there. It’s time not just to work on your personal growth, but to actually get out there and practice because the you that you have become is a different you than you were. And that’s going to change the people you meet. It’s going to change how you date and how you interact.

Different Kinds of Bravery

Different kinds and ways to cultivate bravery
Photographer: Thomas Verbruggen | Source: Unsplash

That is a beautiful, hopeful, and true part of this journey and why I believe so deeply that your search for love is one of the greatest, greatest missions of your entire adult life. It’s a truly epic journey of growth. So there comes a point where it’s time for bravery. I mean, all of the inner work is brave, too, but there comes a time when it’s time for the outer work of bravery, of getting out there and getting out there in different kinds of places and in different kinds of ways.

We’re going to talk about all of those different kinds of braveries. First, I want to just talk about getting out there in general. I want to say I remember at a certain point a very wise dating mentor of mine, a buddy of mine, a friend, I was talking about how I really didn’t want to start dating yet until I lost this next 10 pounds. Because as a gay man in New York City, hello, that’s really important. That’s what I said to him, thinking that my logic was absolutely unassailable.

He said to me, “Ken, do you really, really think that someone who’s going to be attracted to you 10 pounds thinner would just not be interested in you at all 10 pounds heavier?” And I thought, “Well, that’s interesting. Maybe you’re right.”

So what I want to say to everybody is it’s time to get out there now. If you have a serious and unstabilized psychiatric condition, it’s time to address that first before you go out there.

The Power of Getting Out There

If you have an active addiction, it’s time to address that first before you get out there. But other kind of things, just get out there and start working on those things, and start learning as you go. Getting out there is a really, really big deal. So don’t think you need to lose those five pounds.

Don’t think you need to fix this emotional issue and that emotional issue first because you can do it faster, and quicker, and more powerfully in the context of current relationships. We keep thinking we need to fix stuff in our head. But the truth is stuff rarely, rarely, rarely gets fixed in our head. It gets fixed in relationships. So that’s the first thing I want to say, is to mention the power of getting out there.

So if you’ve been afraid to get out there. And next I’m just going to talk a little bit about where to get out there, too. But if you’ve been afraid of getting out there, I just want to say find a pal. If you can’t do it alone, find a pal and make a commitment and make a promise or have that person drag you out with them. Or both of you do it together, but get out there.

And next I’m going to be talking about get out there to a place where you’re going to meet people who share your values, because that’s the best way. And of the gender where there are people of the gender that you’re interested in or the genders that you’re interested in because that’s the quickest way to meet somebody.

An Act of Bravery

I’ll just share a story with you. I was writing my book. I was teaching all this material. It was like 10 years ago. Nine years ago, actually, just about nine years ago. I was single, and Provincetown gay men, gay family week was taking place. I wasn’t going to go because I hated the discomfort of going to these events. Even with my wonderful little kid, it’s just so hard to get out there, as most of you know.

I got yelled at. I get yelled at by two people who adore me. They said, “You are going to this.” I was like, “Yeah, but everyone’s coupled. I don’t really want to. I got other things to do, and it’s expensive.” I was literally nailed by these people who loved me, and they said, “You go. You are going! You are going!” Faced with the intensity of their kind of strong feedback, I said, “All right, I’m going.” And I went, and I met my love there. I met my husband there. We created and joined our families because I committed that act of bravery.

Would I have committed it alone? Even though I was writing this book, even though I was lecturing, and teaching, and doing psychotherapy, no, I would not have. I needed a kick in the butt from someone who really loved me and really saw me. So we all need ongoing vitamin B12 shots of people kicking us in the butt, or supporting us, or going with us. We all need that. It’s so hard to do this alone.

Next, I want to talk about going to places where you meet people who share your values. Now, it’s so easy to just sit around in your jammies online and do your thing.

Finding Love in Real-Time, Real Life

I am not against online dating at all, and I’m going to talk about bravery as well in online dating. But I do not want to pretend that the best, best, best way to meet people isn’t to go to events with people who share your values because there’s a sense of chemistry that you feel. There’s something that happens, and you get to practice your skills in different ways.

In my experience as a psychotherapist, I would say without a doubt, unequivocally, the most surprise, fabulous meetings of people who turn into life partners for people happen in real-time, in real life.

Now, once again, I am absolutely not against harnessing the power of the internet. Not only am I not against it, I am absolutely all for it. But you can be brave there, too. For example, you can go to niche dating sites, and there’s 10 million of them, of people who share your values. That’s one thing you can do.

You can also be kinder and more present. You can stop swiping so quickly and take time to get to know people more. You can show not a quick airbrushed version of yourself but your real self from the get-go and look for other people that have the maturity and the depth to be able to do that, too.

You can ride against the tide of online behavior because online kind of apps sculpt jerky behavior. But you can go against of kind of ignoring people, and benching people, and ghosting people, and one-second replies, and coldness, and harshness, and unkindness. You can go against that tide and show your beauty, your decency, and your goodness. That’s going to save you vast amounts of time. It’s brave. It’s beautiful. It’s authentic.

Being Yourself: A Different Kind of Bravery

Cultivate bravery by being yourself
Photographer: Alexandru Zdrobău | Source: Unsplash

But also, when you do that, you look for other people that are smart enough, wise enough, and kind enough to do the same, and they are going to be your people. So in person or not in person, you can also practice being brave enough to show who you really are, not this airbrushed version of yourself, but the real beautiful, authentic, natural you. That’s a conscious choice, and it’s an exquisite choice. Does it make you more vulnerable? Yes. But does it make you stronger? Yes.

Because when you make that conscious choice, there’s a way that you’re dignifying your authenticity. And there’s a way that you’re going to be much less likely to tolerate people who ignore you, neglect you, and step on you. Because you’ve committed an essential, original act of dignity by saying,

“I’m just going to be me, and I’m just going to look for the people who appreciate that and with whom I feel safe, and good, and right.”

The things I’m saying will change your dating world. All of these things truly, truly will. That’s why this is like a mountain climb towards your own greatness as well as towards your own partner. So when you meet the people, you get to be brave enough to show your real self. You also get brave enough to honor your nose.

Someone seems superficial, someone seems jerky, someone seems nasty, someone seems unavailable, you might want to take a minute to see if it might be your fear speaking. But if intuitively that’s what you feel, then you get to commit the brave act and let me tell you this is hard but it feels really good, of honoring your “no”.

Be Brave to Embrace Your Yeses

When your insides say no, you honor it, no matter how sexy that person is. Because people who are not good for us and not available often are more sexy. I’ve talked about that in previous episodes and we’ll speak about it again.

Next, that you are brave enough to embrace your yeses. If someone seems lovely, if someone seems exciting, you approach them, you go after them and you do it in a good way and you do it in a smart way, but you don’t let it go.

In my old Deeper Dating events, which were in-person events, that was one of the things that we taught. We taught people how to go up to strangers, how to smile at strangers. People said it was so hard, but they began to develop that muscle. When they were in line at Starbucks, they would turn around and say hello to somebody. That’s the most brave act of all. It enlivens you, and it helps you find love.

That’s another kind of bravery, is being in the moment, alive, and current, and kind of willing to just talk to people. I’m going to read a fabulous paragraph here from the author and blogger Sarah Bridge. This was her blog post. It was called Do Single Events Make You Feel More Single? This is what she wrote,

“I’m learning to make every minute a potential door to a date.

I sit at the front of the bus now, and I make eye contact with people rather than heading straight out straight to the back or looking at my phone.” I added that, that wasn’t in there. “I take different routes. I visit different places. I get out of my routine.”

What Is Brave For You?

“I walk with my head up with open body language and I smile or I even chat with complete strangers in the coffee house, in the coffee shop, at the supermarket, or on the lift at work. People have actually been astonishingly receptive. It seems that everyone is looking for an in, a reason to say hi. And it is nerve-wracking, but fun and an ego boost when a smile or overture is returned. Now that I’ve started looking around, it seems that everyday life is full of friendly, single guys while dating life, well, not so much.”

So if finding beautiful, healthy, real love is important to you, it’s time to amp up. This amping up will connect you to your greatness, to your possibility, to your sense of adventure and to do that by infusing acts of bravery into your search for love. And now we’re going to get into how to do that.

I’m going to offer two exercises. As you listen, just think about this and kind of grab on to one thing and say, I’m going to give this a shot. The first is, it’s kind of really asking yourself, based on what we talked about here, what would be brave for you? What could you do that would amp up the bravery dimension of your beautiful, precious, big deal, important search for love? Take a minute to think about that.

Next, I’m going to offer you a practice. This is a fabulous, fabulous practice, a really, really wonderful one. It’s the practice of having an intention. So when you have an intention toward growth. Let’s say you’re going into a first date. Let’s say you’re sitting down in front of your computer and you’re going to do something online.

What Is Your Brave Intention?

Or you’re on your phone and you’re going to do something online, or you’re going to a party or anything like that, or you’re going to Starbucks. You create an intention that captures kind of the person you want to be, your kind of next brave step. Maybe your intention is that you’re going to smile at people and you’re not going to spend all your time looking at your phone. That’s one intention.

Maybe another intention. This was a really, really brave one. Someone taught me this, and for years I thought never in a million years could I do this. But I did end up doing it, and it was great. It was to go into a club, this was in the days that I was going to clubs a lot, and actually approach 10 people I was attracted to, 10 people.

In other words, garner 10 rejections or close to it. I thought I could never do that, but I did it. I did it. I decided I was going to do it. It was pretty bad in that literally 10 people were not interested in me. Every one of those 10 people was not interested in me. I know that I would’ve walked away previously from an experience like that after one or two just completely deflated, and sad, and time for the ice cream.

But I left this club actually feeling pretty damn good because I had said yes to my intention. And my intention was not about being liked and not about not being rejected. My intention was about being me and being brave. So you think about an intention, and you set it. Your definition of success is going to be – I approached people I was afraid to approach.

Build Muscles of Bravery

Even if nothing happens, you did that. You succeeded. I’m going to smile and be friendly. I’m not just going to stick with my friends. I’m going to, whatever it is, and you craft an intention. Here’s what’s going to happen. You’re going to feel brave, you’re going to feel like you’re growing. You’re going to learn something. You’re going to build muscles of bravery that will help you in a future situation.

All of these things are going to happen. And here’s another fabulous thing that’s going to happen. There will become a ray of hope that you will feel in your dating life because you will be growing. You will become stronger. You will be becoming stronger. So, try this.

Go to, and you can go to Ask Ken. I’d love to hear your experiments with bravery and how they go for you. I’d love to share them with people in the podcast. So please, please reach out and do that. That would be a wonderful thing. It’s going to help other people, too.

Also, if you liked this episode, please subscribe on Apple Podcast or elsewhere and leave me a review. That is a tremendous gift. Thank you. Have fun with your personal adventures of bravery and authenticity. And I will see you at the next Deeper Dating podcast.