3 Ways to Deal With Rejection in Dating

When it comes to dating, does the fear of rejection stop you from being yourself?

In today’s video, I’m going to give you three secrets to changing your relationship with rejection . . . Someone out there is going to love the unique things you have to offer, and I can’t wait to hear what happens once you’re no longer letting the fear of rejection hold you back.



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In this video, I’m going to give you three secrets to changing your relationship with rejection. Are you someone who suffers from the anxiety of getting rejected? Does it stop you from taking risks, whether it’s approaching someone in real life or messaging someone on an app, or going on a first date with someone? Maybe you just feel this socially in general, this sense of anxiety at talking to other people and them rejecting you. You might even feel it in your professional life, that there are risks you don’t take, there are calls you don’t make, opportunities you don’t ever put yourself up for because you’re terrified of the rejection that could ensue. So how do we begin to reduce our sensitivity to rejection?

Number one, appreciate that rejection is complex. Other people have all sorts of reasons for rejecting us. It might be that you’re not their type, which has nothing to do with how attractive you are. It’s just that you’re not their type. It may be that they’re looking for something superficial, purely. It might be that they are still hung up on their ex. It might be that they’re hungry. It might be that they weren’t hugged enough as a child. There are so many reasons why someone might have rejected us that have nothing to do with our true value. But what we do in those moments is our ego takes our biggest insecurity, the way that we are terrified that we are deficient and it makes the rejection about that.

“Of course, they didn’t like me because I’m not pretty. I’m not interesting, I’m boring, just as I had suspected. They don’t like me because I’m too old.” We take our biggest insecurity and we make that the entire story. Even as you’re listening to this, there will be some people who are going, “But that is the story.” That’s what our insecurity does. That is the story. Let’s just play a thought experiment for a moment. If someone decides that you are not for them because of your age, that to me, isn’t even as simple as you got rejected because of your age. That person has a story in their head about age. There are so many factors that have been leading up to this moment for them that have created a story about age that make them your wrong person.

If someone decides to reject you based on a physical feature that they don’t like, and you think, oh, see, I’m not pretty enough, you’re dealing with a complex story there. You’re dealing with a person operating on a certain level of, the person that I fall in love with has to look exactly like this. Therefore, we’re dealing with all sorts of issues of what that person is open to, the ways that person has constrained themselves in their love life, the way they have a very one dimensional view of what attractive is. This is still a complex issue even when they’ve told themselves it’s about this very specific thing. So don’t just take your thoughts less seriously, take their thoughts and judgments less seriously too.

Number two, root your value in your character. When we are rooting our value in these superficial factors that we ultimately don’t control, we are always going to feel vulnerable. I have come to believe so much in my life, in the value of doing things every day that contribute to your character, your integrity, the kind of person you want to be. Make moves every day that bring you closer into alignment with the values that you want to practice in life. The antidote to the person who thinks they have no value whatsoever and the person who thinks all their value is in something superficial, like their looks, is to do something today that makes them genuinely proud of themselves. If we make ourselves proud for being the human that we want to be, not for having the impressive thing we want to have, but for being the human, being the person we want to be, we will start to worry less about whether someone else likes us, because the more proud we make ourselves, the more we will come to like ourselves. And we won’t look to the outside world to validate us in that way.

I know that in the last few years of my life, I’ve gone through several different major challenges. My having dealt with those challenges and the way that I’ve shown up in my life and the loving person that I’ve been to people in my life and the ways that I’ve been strong and resilient have built an immense amount of pride in myself. And it doesn’t mean that I have absolutely zero sensitivity to rejection. It just means that there’s only so much that someone, especially someone who doesn’t know me that well, there’s only so much they can do to get through because I’m really proud of myself. No one can take that away from me. I’m really proud of the person that I am.

What that means is I don’t actually put my stock in some of the superficial things that I might have put my stock in as a younger man who was, if I think of myself at 21, looking across the room and sort of wanting to know if that person over there thinks I’m attractive. Can I tell from the way this person is looking at me that they think I’m good-looking or attractive? That’s me putting my stock in something else. And I don’t put my stock in that anymore.

It’s not that I don’t like to look good. It’s not that I have zero vanity. It’s just that really isn’t, that’s not what I really give a shit about being judged on. I don’t put a picture on Instagram and wait for people to go, you’re so good-looking, you’re so this. I don’t give a shit. I really don’t, because that’s not where I put my value.

And so, at some point we all have to ask ourselves, where am I putting my value? Am I doing things each day that add to my sense of value, because I’m being more and more of the person we want to be? That pride in ourselves, it’s not free. We all have value intrinsically as human beings. I’m sure we all believe that, but that doesn’t mean that liking ourselves is free. We don’t just wake up one day and go, I like me, unless we’re doing things that make us proud. And it’s all those little things that we can do, whether it’s the way we show up for our friends, if it’s, instead of focusing on pouting in a social environment, it’s actually focusing on going and connecting with someone, being brave and saying, hi, to somebody or smiling at somebody.

Jameson put it beautifully earlier, it’s not valuing your symmetry, but valuing your smile, how much can I actually be an approachable energy in a room? How much can I be kind or add to that sense of fun in the room? Can I go to the gym today? An act that will make me feel proud of my discipline. When we are proud of ourselves, we’re not looking for it from the outside world in quite the same way anymore.

Secret number three to galvanizing ourselves against the negative effects of rejection is, go slow to go fast. Rich Roll, the now world-renowned podcaster, an ultra-athlete, talked about his days in AA, in recovery from alcoholism. And he said that there was a time in AA where it felt like everyone was kind of overtaking him. His friends were achieving things and going places and making things happen, and he was stuck in AA meetings. But his time in AA meetings, who he became, the ways he became proud of himself, the confidence he built in a very grounded way, that laid the foundation for the success that came later on, on a longer timeline.

I think our love lives are like that too. I think that there is this feeling that when we are working on ourselves in the more subtle ways that don’t always get noticed immediately, we’re getting left behind. That person who looks a certain way, who has that Instagram profile that makes them look extraordinary and beautiful and sexy and gets lots and lots of attention, that they’re somehow winning that race, and we are getting left behind. I actually don’t believe that. I think that the really courageous thing to do is to start proactively working on ourselves in ways that no one else can see, but have the faith that that will attract someone of true substance in the long term. Because when someone who has done the work sees someone who has done the work on themselves, that person stands out, perhaps more subtly, but much more profoundly. And that then becomes the basis of a real and lasting relationship. It’s not about trying to attract the maximum number of people, it’s about becoming a person of value and then finding someone who uniquely values what you have to offer.

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