Disappointment is one of the toughest experiences in dating. And somehow, it keeps showing up again and again. In this episode, you will learn new ways to deal with disappointment so it doesn’t mess with your self-worth, but actually makes you wiser, stronger, and more capable of finding love.

If you love the Show, please Subscribe, Rate, Review and Share on Apple Podcasts, or your favorite Podcast Platform! Click here to learn how.

 

Listen For

• 00:54 – What is the role of disappointment in dating and the skills we need to develop to handle disappointment?
• 07:55 – What is the difference between disappointment and rejection?
• 14:01 – How do you hold and process disappointment?
• 18:46 – How do you use disappointment to communicate your needs and build healthier relationships?

 

Important Links

Get a copy of Deeper Dating by Ken Page

Join the Coaching and Mentorship Intensive with Ken Page

Connect with us on Instagram

—

Watch the episode here

 

Listen to the podcast here

 

How To Turn Dating Disappointment Into Dating Wisdom

Disappointment is one of the toughest experiences in dating. Somehow, it keeps showing up again and again. In this episode, you will learn new ways to deal with disappointment so it doesn’t mess with your self-worth, but makes you wiser, stronger, and more capable of finding love. Stay tuned to the Deeper Dating Podcast.

‐‐‐

Disappointment Is A Core Part Of The Dating And Intimacy Journey

Hello, and welcome to the Deeper Dating® Podcast. I’m Ken Page. I am a Psychotherapist. I’m the Author of the bestselling book, Deeper Dating, and your host of this podcast. Today, we’re going to talk about something that I think does not get enough attention. And that is the role of disappointment in dating and the skills we need to develop to handle disappointment.

Before I get started, I want to say that if you would like to know more about the Deeper Dating® path to intimacy and love. Go to DeeperDatingPodcast.com. There, you’ll find episodes of something like 230 episodes and transcripts of each one. And also, if you go there, you can sign up for my mailing list, and you can get a free eBook called The Five Keys to Deeper Intimacy, which teaches you the skills that I think are the key skills in having a richer intimacy life. Almost all of those have gone viral on Psychology Today and elsewhere. You can also find that by going to DeeperDatingGifts.com. With that, I’m going to jump in.

I’ve learned so much from being a psychotherapist for 40 years specializing in the skills of intimacy, and as a human being, learning and growing myself. But I think that I learned, in some ways, the most from the years when I ran deeper dating intensives. Where I’d work with small groups of people over six months and help them take each of the steps of the deeper dating journey and deal with the bumps along the way in a very intimate way.

One of the greatest learnings that I had from all those years of doing that, and I’ve taken a pause now because I’m creating an event for single people who want to make a difference in the world and build community and find love as they do that. You’ll be hearing more about this if you sign up for my mailing list at DeeperDating.com.

Anyway, one of the biggest things that I discovered is that disappointment is not an anomaly. It’s not something that shouldn’t be there. It is one of the main segments of the intimacy journey and definitely of the search for love. When we think that we need to get rid of disappointment, that it’s a sign that we’re not doing something right. Then we skip over a step that’s incredibly important, and we don’t learn a skill that is so essential to learn because it’s part of the fabric of dating and finding love. In different ways, it’s also the fabric of being in an intimate relationship.

Disappointment is not an anomaly. It’s not something that shouldn’t be there. It’s a key part of the intimacy journey and the search for love. Share on X

Again and again, I saw, including in me, that people assumed that disappointment should be gotten over quicker than it is gotten over. That we should move past it more quickly. And if we don’t, we’re wallowing, we’re insecure or we’re lazy, or we should get over it and get back on the road, and start dating again. And it does not work like that. Again and again, as I worked with people who were consciously addressing their search for intimacy, they would have experiences where there would be growth, and there would be change. Hence, there would be hope.

Let’s say, for example, somebody would learn how to honor their Core Gifts. Learn about the difference between Attractions of Deprivation and Inspiration. All of which we teach in this work. They’d be excited. They’d be happy. They’d be living this, and they would, all of a sudden, notice that they were meeting kinder, more available people who accept them more for who they are. They would meet someone like that, and let’s say it wouldn’t work out and the pain was pretty severe because their hopes were higher.

Again and again, I saw that they would berate themselves for the depth of their disappointment. They would think that they needed to just get on with things. And again and again, I saw that the act of dignity in moments like that is to honor our disappointment and pain, to make room for it, to get support, to grieve, to be frustrated, to be sad, to decide we want to pull back, to maybe hibernate a little bit, to take a break from dating, and to take a break from online dating.

Whatever it is that we need to do, that actually disappointment consistently hurt worse than people thought it should, and last longer than people thought it should. What I discovered and what we discovered as communities together is that that’s not how it works. When we are disappointed in love, and God knows the world of dating is filled with disappointment. It’s part of the fabric of dating. You’re going from taking a total stranger and hoping to make them your home in the world. How often is that really going to happen? How many people have been beaten up and have been made afraid?

This culture of unkindness in dating stimulates negative qualities in us. It’s so understandable for these and many other reasons, including our own fears, that there’s going to be a lot of disappointment along the way. We can work with that disappointment in a different way and actually turn it into fuel in our search for love and our intimacy journey. I’m going to be talking about how we can do that. I want to offer two thoughts about the first step here.

 

What do you do when you’re disappointed? Let’s start within dating. For example, there’s someone you’re excited about and who you met online. You had a few really good conversations. And, all of a sudden, they disappeared. How many of us has that happened to or there’s someone who we’re excited about? And they seem interested in us, and then they tell us that they’re not interested in us for whatever the reason, or we discovered that they were being dishonest about who they are. These are some examples that are more likely maybe to occur in online dating.

The Difference Between Disappointment And Rejection

In real dating, you meet someone that you’re really excited about. Maybe they even feel like a revelation to you, and they’re not interested, or they’re not available, or they’re too busy. It hurts and it’s disappointing. The first concept is something that I heard from a graduate of the Deeper Dating® Intensive who is in our graduate coaching program. She said something so wonderful. She said she’s learning that there is a difference between disappointment and rejection. The disappointment is the feeling that you get when you’re disappointed, when you were hoping for something, and it didn’t end up happening, or someone let you down.

Rejection is the feeling of, “I am being rejected for who I am.” Rejection includes self-rejection. That’s when we go into those really painful places of, “I’m not thin enough. I’m not smart enough. I’m not confident enough. I’m not successful enough. I’m not whatever enough or I’m too this or I’m too that.” That’s the space of self-rejection. We can tell ourselves that we are being rejected, and that hurts more deeply than saying, “Ouch. I am disappointed.”

Disappointment is more like staying in the moment. Yes, it hurts. It aches. We feel a loss, and that is real.” But it’s different than turning it into, “I’m being rejected for me.” When we can allow space in our nervous system for the sadness and the ache of disappointment without calling it this kind of deeper, more existential rejection, but just feel the sadness of disappointment. And don’t turn it into a kind of self-referencing of, “I’m not worthy. I’m not attractive. I’m not good enough or even, this person thinks I’m not attractive enough and I’m not worthy enough.”

When we share our pain with a loved one, it eases, dissipates, and diminishes. We’re no longer holding it alone. Share on X

Holding the disappointment in our nervous system, it sucks. It hurts. It aches, and it feels kind of unbearable, but it’s not unbearable. We can hold it, and we can live with it. How do we live with it? What are the keys to living with it and experiencing it as disappointment instead of turning it into a cognitive structure of self-rejection or rejectability? Which God knows we all do. You could see that this is a skill that we can cultivate. How do we cultivate it? A few different ways.

First of all, we get support. We complain. We cry. We share it with friends who are not going to tell us that we did something wrong, but are going to be there for us and be supportive. The brilliant Buddhist Monk, Thich Nhat Hanh, is someone I adore. If you don’t know his work, you should get to know it because it’s glorious. He talks a lot about suffering and how to hold suffering and this is what he said. He said, “If you take some black ink and you pour it into a glass of water. It will cloud the entire glass. You won’t be able to see through it.” That’s what it’s like when we hold disappointment alone.

If you take that black ink, not a very nice ecological image, but still. You take that black ink, that vial of black ink, and you put it into a big river. It dissipates fully, and it’s not noticeable. Something akin to that happens, although, of course, it doesn’t dissipate completely. Something akin to that happens when we share our pain with a loved one. It eases. It dissipates. It diminishes. We are not holding it alone. I think that’s a really big step one.

An equal and parallel step 1, or maybe step 2, or maybe the real step 1 is holding our disappointment and saying, “I’m disappointed. I’m sad. There’s an ache inside me. That was something I wanted. Ouch. Ouch.” Holding and walking with and being with that ache is worlds better than going into the rejection state. The first thing we do is we hold it in our nervous system. We breathe. We feel it. We honor it. We put our heads in our hands. We go for a walk. We listen to music, and we allow it to metabolize and dissipate, which it ultimately will.

Where that disappointment takes you—if you hold it with spaciousness and ask, “What’s the learning? What’s the lesson?”—very often, the lesson is: “That was not the right person for me.” Share on X

An image for how to hold that is this image of holding it with cupped hands, which is an image that we use in this work a lot. If you take your hands and you cup them. And you could even try it now. As if you’re holding a baby mouse or a baby bird or a butterfly. You’re cradling it. There’s a feeling of cherishing, but there’s also a feeling of space. If you hold your disappointment with those kinds of cupped hands, cherishing care, space, and allowance. You will be in some kind of a state of sadness and grace at the same time. That is an okay place to be.

That’s a thing that we can do. We cannot turn it into the cognitive structuring of rejection. We can hold the sadness with cupped hands. We can talk to friends about it, too. Another really, really important thing to do. We allow it to take its course and that course might be that we need to take a break from dating. We do not want to take a forever date from breaking. The more you allow yourself to do this consciously with cupped hands and don’t turn it into rejection. The more you’re going to be able to take this like a rocking motion. You pull back for a while, and then you come forward.

Holding And Processing Disappointment With Support And Spaciousness

Some people in my intensives, actually in the discovering of deeper self-love and the disappointment of some of their experiences, decided to take a break from dating altogether and found that really deeply enriching. You know, it’s like an artist who goes through a period of a particular kind of art that they do. They need to immerse in that and live it and express it before they can move to whatever is next.

Where that disappointment takes you, if you hold it with spaciousness, if you think, “What’s the learning? What’s the lesson?’ Very often, the lesson is, “That was not the right person for me. They disappointed me because they were not the right person. They were not interested in someone like me. They did not see my Core Gifts.” Please, look at the material that I’ve written and taught about Core Gifts. Because often, we judge ourselves for the qualities that are the very qualities that are our intimacy superpowers, that some people couldn’t handle.

So, we decided that they were not gifts, but in fact, they’re some of our greatest gifts. This is one of the bittersweet and ultimately magnificent learnings that we do in our intimacy journey. Is that so many of the things that we were taught were not attractive, were not desirable, and were just too much for the other person, but valuable, and precious, and parts of our own genius. You can explore tons of my episodes where I talk about Core Gifts, and I encourage you to.

Another thing that happens, if you don’t sink into the bitterness of the conceptual framework of self-rejection or unworthiness or undesirability, but you instead see it as part of a bumpy journey. And damn, it is a bumpy journey. It is. Another thing that happens is you start to externalize responsibility appropriately. That doesn’t mean all women are this way, or all men are this way, or all non-binary people are this way.

I don’t mean that kind of externalizing of responsibility. I mean, being aware if someone didn’t show up, if someone was critical, if someone left you with a kind of cold feeling in the bottom of your belly by the way that they are. If someone was unkind to the waitstaff, instead of immediately thinking, “How was this me?” Allowing yourself to reasonably think, “What were the negative qualities here?” If you’ve studied your own attraction patterns, kind of become a student of who you tend to be attracted to, who has broken your heart, and where are there repeating patterns.

Disappointment brings rich, powerful learning—but only when we give ourselves space to feel the pain, the frustration, and all the emotions that come with it. Share on X

You might notice certain negative qualities in that person that previously, when you saw those qualities, you were kind of attracted and thought, “Why can’t I be more like that?” Or maybe you thought, “I could change that about this person.” Now, you’re thinking, “I’m externalizing responsibility. I’m seeing this quality, and it makes sense that we weren’t a match. It makes sense that this person didn’t get me.” This allows more space.

When you’ve let yourself externalize responsibility in a reasonable way, and you’ve taken yourself to the degree possible out of that rejection conceptualization. And you’ve allowed yourself to hold your disappointment, made space for it, retreated, and taken care of yourself if you need to. When you’ve done all of those things, you’ll also be in a better position to think, “What was me here?” Not that that’s not good to think about the whole way through. But if you take care of yourself first, you’ll be more likely to be able to do that.

“What were the patterns that I was playing out that might’ve contributed to that?” For example, how was I playing it cool and not showing my heart? Which might’ve left the other person with a feeling of, “Do they like me? Do they not like me?” How might I have expressed judgmental-ness? How might I have kind of shown resistance or taken a long time to get back to the person or any of these things? What is there that I could have learned from this experience?” That is another way that you empower yourself.

Using Disappointment To Communicate Needs And Build Healthier Relationships

There’s rich, rich learning that comes out of disappointment and powerful learning. But it comes best when we don’t flog ourselves into that state. We allow ourselves the room to feel all of these different emotions. The pain, the disappointment, and the need for space. I think that we go into the dating world thinking that we don’t need that, and thinking that if it happens, it’s kind of a negative anomaly. In fact, it’s part of the process. Holding ourselves with grace makes a huge difference.

Let me also say that for those of us in relationships, disappointment plays a huge role, too. When do we feel disappointed by our partner’s response? When do we feel disappointed in our response? How can we let our partner know what we want? This is an amazing thing that people don’t realize, I think. Super, super important point. Telling your partner or the person you date what it is that you really need or want. Doing it in a way that’s not criticizing them, but giving them an opportunity to give that to you actually often feels like a very generous gift. It’s also vulnerable, and that’s a desirable trait.

 

It’s important that we let ourselves show what we need, what we want, and we kind of prefigure, “If I don’t get that, I’m going to be kind of disappointed.” Then, we think, “Does that fit that I could ask for that? How could I ask for that in a way that allows space for the other person?” The act of doing that proactively is a huge, huge thing. It makes the relationship more alive. It saves you and your partner from dealing with so much disappointment. When your partner doesn’t meet your needs, you can let them know how you feel and what it is that you want.

I think that the more that we do that in a kind of strong and clear, and how do I mean strong? I don’t mean strong like coming on strong. I mean it’s like a muscle that we build. A muscle that gains strength, which is that we graciously and unashamedly say and ask for what we want in kind and generative ways. Learning how we’re disappointed in our relationship tells us worlds about what we want, what we need, and what we’re ashamed to ask for, or how we ask for the things that we want in ways that aren’t helpful. Those are some ways of working with disappointment in the relationship. As they say, all relationships are a process of rupture and repair.

Holding our disappointment as something valuable, as something almost sacred, as something that we can learn into is an incredible act of maturity, dignity, and it moves us into the potential for much deeper relationships and helps us move out of the pain of disappointment more quickly and with more positivity and more hope. So, disappointment is on our plates. It’s part of what happens. Practice holding that with kindness. Practice holding that with cupped hands. Practice holding that with support, and watch what changes for you. Thanks for listening. I look forward to connecting on the next episode of the Deeper Dating® Podcast.

 

Important Links

• Thich Nhat Hanh
• Deeper Dating: How to Drop the Games of Seduction and Discover the Power of Intimacy
• The Five Keys to Deeper Intimacy
• Deeper Dating Gifts
• Deeper Dating Podcast