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7 Reasons Why Dates Don’t Work

Updated: Sep 22, 2022

7 reasons why dates don't work

Are you tired of the dating scene? Sick of superficial interactions? Do you leave dates and singles events feeling more lonely and discouraged than when you got there? How many times have you had an experience like this one: You’re about to go out on a date. You dress your sharpest, check for spinach between your teeth, make sure you have breath mints, square your shoulders, put on your best face, and out the door you go (or to your computer perhaps, but at least you make sure you look decent from the chest up:-)

Only to find out, 10 minutes into the date, that you wish you hadn’t gone, that there is no way this person is relationship material, and what were you thinking, anyway. Sound familiar? Well, you’re not the only one who feels like this. You probably already know that the dating scene doesn’t work. So don’t take it personally. You are set up to fail before you even show up. It’s not because you’re “flawed” somehow, or “messed-up”. And it certainly isn’t because there aren’t any good men, or fabulous women out there.

It’s the “dating system” that is flawed. It’s the whole dating setup that is messed up, and when you do it the traditional way, your chances of success are slim (also listen to our podcast, Dating, Style)

That also explains why it doesn’t take care of you to simply learn a new great communication technique, or join another online dating platform. You bring with you to each new interaction the same old ideas of how to do date. What you need is not fancier wrapping, it’s new and improved content!

The 7 reasons why dates don't work as you'd hoped

  1. The List

  2. Trying too hard

  3. The Single mindset

  4. What you think you want

  5. Wanting keeps you from having

  6. Waiting instead of creating

  7. Dating is relating

Now, let’s explain these reasons.

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1. The List

Your “list” of what you want in a partner prevents you from actually being with the people you meet. Because of that, relationship can’t develop. Relationships don’t grow from lists or plans.

Relationships grow from the connection that is present between you, and if you’re not present to it, you will miss even the greatest of opportunities. You end up having a relationship with your comparative list instead of the human being across from you. Also, when you’re comparing the person to your list (which you do whether you notice it or not), you’re “in your head” and not in your heart, which is where Love lives.

2. Trying too hard

You try so hard to impress each other that authenticity goes out the window. Relationship can’t build when people are hiding, pretending, or trying too hard. It’s like two people holding up big cardboard smiley faces in front of themselves and hoping the smiley faces will fall in love with each other. Smiley faces don’t fall in love. People do. Relationship flows when people are honest and real, showing the other person who they actually are, not who they ought to be, or what their image of themselves is. Relationship builds when people dare to be real and relate to one another heart-to-heart.

3. The Single mindset

Your identification as a single person keeps you stuck in a single mindset. When you say, “I’m single”, you state it as declaration of fact; as a part of who you really are, instead of as a temporary situation that can and will change (if you desire it to change). From your identification with being single, you cannot be in relationship. I (Christian) remember when I was single for many years in my late twenties and early thirties. As more and more of my friends got married and had kids, they had less and less time to hang out with us singles. So we hung out together, did “singles things”, went to “singles events”, looked for other singles, talked about singles … it was as if my identity as a single person got more and more solid and fixed, became self-reinforcing and hence more difficult to change.

To create a relationship, you need to take on a relationship mindset. You need to be able to visualize yourself as being in a relationship. Begin to see yourself in relationship to others – the person you interact with at the post office, grocery store or church. See yourself being in relationship wherever you go, including on dates. This will create a powerful energetic shift in your interactions and will allow for more relatedness and connection. Remember, a date is a mini-relationship, even if it only lasts half an hour and you never see that person again.

4. What you think you want

What you think you want is not really what you want (this is just as true for people in relationship). This keeps you from getting what you want. Most of us go through life chasing what we think we want, and when we find it, we find ourselves disappointed, because it wasn’t really what we wanted. Let’s give an example. You think you want to find a handsome man with a healthy career who likes taking walks and loves to cook great food. You think that’s what you want. But that is not what you really want. At least, it’s not the essence of what you want.

What you really want is a certain lived experience with someone. The only reason you ever want anything is because you imagine you’ll have a certain feeling experience if you get it. Go for that experience.

Think about it this way: Can you have a horrible experience with someone who is handsome, has a great career and loves to cook? Yes, of course. Can you have a great experience with someone who is a lousy cook and is in between jobs? Of course you can. And what would you pick if it came right down to it?

A lot of times, we are so busy looking for the handsome, rich, pretty ones that we don’t recognize the wonderful people we come across every day with whom we could experience all of what we really want.

5. Wanting keeps you from having

Wanting a relationship prevents you from having a relationship, so unfortunately, the more you long for a relationship, the more you can’t get the relationship. Did you know that “wanting” and “having” can’t exist in the same space, at the same time? This is one of the biggest obstacles to creating a fabulous relationship. You want it so much, which is natural and understandable, but still, the harder you want a relationship, the less you have one!You have to learn how to move out of wanting, into having. Only then can you have anything you dream of in relationship.

6. Waiting instead of creating

You show up to a date to just to “check it out”, to see how you feel about this person. As if you are a passive observer of a movie. Since both of you show up to just “check it out”, you’re waiting for the other person to provide the content, to somehow show you if they have anything of interest to offer. In other words, you both show up waiting for the other one to be interesting. It’s like showing up to a potluck where everyone came to eat, but no one brought any food! It feels flat, pointless, and unfulfilling. You need to learn to create on dates instead of waiting for anything meaningful to take place. Once you start creating, you have moved yourself into the realm of infinite relationship possibility. You have declared yourself the master of your life experience. And your dates will be way more satisfying.

7. Dating is relating

You think dating is different from being in relationship. You view dating as the means to get into relationship, and once you have “found” a relationship, only then do you begin to be in … well, relationship! Dating is no different from being in relationship. A date is a relationship, albeit a short one. If you let it, and if you know how, dating can be an exquisite and enticing part of being in relationship.

These are only seven of 20 reasons why dating as you’ve always done it doesn’t work.

A great teacher, Wayne Dyer, once said, “We don’t get what we want, we get who we are.”

If you aren’t getting the dating experiences you want; if you aren’t getting the relationship you want, it’s not because there’s something wrong with you. More likely, it’s because of how you show up and how you don’t let yourself be all of who you are.

The good news is, that can change. Dating doesn’t have to be this way. You do not have to wait until you find the perfect partner before you can experience love, and be intimate and happy. There’s a whole new way to be in relationship with the people you date that is rewarding, fulfilling, intimate and nourishing.

So how do you do that? Start by reading this article again and implement what you can from the 7 points we made. Remember, this post isn’t really about dating techniques or how to fix a broken dating system. It’s about a new way of relating. Then check out our audio presentation “Why Am I Still Single: 20 Reasons Why Dates Don’t Work”.

From this new point of view, dating can show up as a rich opportunity to be in relationship, an opportunity to enjoy precious connection with another being, no matter whom you’re dating. Whether you want to see this person again or not becomes unimportant, because you’re having a great time.

So take heart, there is lots of hope for you and the dating process. Or as we’d like to think, the relating process.

You absolutely can have the dates and the relationship of your dreams!

LoveWorks: We believe relationships are meant to be an empowering, fun, passionate, safe place to grow, love, and learn. Where we get to be more of who we are, not less. We know it’s not always easy, but it can definitely be easier! With our unique and practical approach to relationship, you learn how to resolve conflicts quickly and enjoy fulfilling intimacy for the rest of your life. To learn more or contact us, visit


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