We’ve all been there.  After tolerating so many ho-hum first dates we finally meet someone we click with.  The spark is like WOW and suddenly we feel on the precipice of something big.  We’re several dates and a romantic weekend into it, and our other prospects are beginning to lose their appeal. On the drive home after yet another magical evening you begin wondering, Could he be “The One?” You know you shouldn’t jump to conclusions but every time a silly text message comes through, a smile creeps across your face and your heart feels so happy.

You walk into the front door and hear a text notification bell on your phone.  You smile.  You haven’t been apart for 20 minutes and already he’s sending another silly [undecipherable] emoji message for you to decode… Hi Kate.  I’m sorry but I’m not sure we should keep seeing each other.  I really really like you, but I’m just not ready for a serious relationship.. Maybe something casual could be fun? 😉


Whenever we experience a disappointment or setback in dating, there’s a particular flavor to the let down that’s unlike any other.  Sure it’s upsetting to lose a great job opportunity, but when we feel letdown by love, it’s as if every other romantic blow we’ve experienced since Jr. High comes back to haunt us.

Since disappointment is inevitable in dating, how can we manage these difficult emotions without taking them so personally, or taking ourselves out of the game entirely? The key is to acknowledge and reframe our upset in a way that allows us make generative meaning and then move on.  Easier said than done? Probably, but navigating disappointment is a relational skill, one which we can learn to do better.

Here is a four-step process that will help you navigate dating disappointment and stay on track to love.

Step One:  Feel Your Feelings and Name Them Out Loud

When confronting the reality of someone disappointing us, it’s human nature to wonder why things went a certain way and what you could have done to create a different outcome.  And if you suspect that a miscommunication could be at the root of your breakdown, then you would be wise to try and clear that up.  But if the other party is not open to “discussing” things, or if they have made up their mind and have moved on, then asking “why” is not a generative question (and let’s face it, the answer rarely satisfies the hurt our heart is feeling).

Instead of asking “why” did this happen? ask, how am I feeling about what happened?  Get in touch with where you are emotionally and be willing to sit with and connect with yourself.  Name the feeling you are experiencing as objectively as possible.  Hold space for the possibility that your feelings are covertly disguising disempowering meaning frames, but for now, just focus on naming your feelings. “I am feeling pissed off.” “I am feeling ugly.” “I am feeling betrayed and taken advantaged of.” “I am feeling heartbroken.”

As you uncover the feelings that come up for you, offer yourself compassion and loving space, the same way you would if you were consoling a dear friend or loved one dealing with heartbreak. You wouldn’t immediately begin to “talk them out” of their feelings, you would hold space, bringing empathy and tenderness to this universally human experience.

Step Two: Question the Story You’re Telling Yourself About Why It Happened

Our feelings often betray the meaning frames we’re inside of about why something happened.  And hey, it’s human nature to make our experiences mean things; but if we are not conscious about the stories we tell ourselves, these stories concretize as “facts” that erode our self esteem.  So take a moment and make clear (maybe write it down in a journal) what you are making this disappointment mean.

You might be making “I feel ugly and unloveable” mean: “I’m too old to get what I want in love.” “Men are shallow dogs.” “All the good ones are taken.” Please understand that disempowering meaning frames — the stories you’re telling yourself — are compounding and aggravating the actual loss that you are experiencing.  Even if that loss was only the possibility of something, it is still a loss that you will naturally grieve.  The grieving process however becomes compounded and convoluted when you add in false stories and beliefs that it didn’t work out because something is wrong with you.

Step Three: Challenge the Story

Once you are clear about your feelings and the meaning frames you are inside of, it’s time to bring a little tough love to the table.  You do this not by beating yourself up with “I shoulda, woulda, coulda” platitudes, but by connecting with the authentic part of you who knows how to self-soothe while getting curious about the unhealthy patterns and behaviors that contributed to the situation.

From a place of true curiosity ask yourself:

Why am I disappointed?  Is it because I thought I was “done” dating and wanted to move on to the relationship part?  Is it because I don’t think I can get anyone better?  Is it because I ignored my needs and agreed to casual sex when that wasn’t what I wanted?  Is it because this person gave my life a feeling of excitement that I have been unwilling to create on my own, and now I feel depressed and bored?

Answering these questions will get to the root of your part in the breakdown (even if it’s only 2% yours and 98% percent theirs!)  But if you choose to shift the focus of your attention from the other person back to you, you will move through the remainder of the experience in a way that heals and opens you up to receiving a healthy, happy  love.

Step Four: Focus on the Bigger Picture Not The Person or Circumstance

As any person over the age of 30 knows, life is about connection, growing and learning lessons along the way.  Without seeing the bigger picture, and how our experience is calling upon us to grow, life gets small and each disappointment builds upon the last, creating a state of chronic let down.

Learning is the lifeblood of a person committed to living consciously.

So when faced with a dating disappointment ask yourself the following: What relationship skill am I being invited to cultivate?  Am I being asked to trust my intuition more?  To learn how to generatively engage conflict so that the relationship deepens, or ends sooner?   Am I relying on romantic partners to make life fun and juicy, thereby placing my happiness into the hands of others?  How can I make amends to myself and gift myself the life I deserve regardless of my marital status? How can I create a life of having it all: developing myself, my gifts, and enjoying a passionate and reciprocal loving relationship?

Whatever lesson this situation has taught you, resolve to learn it now, so that you do not have to repeat it again.

Navigating Disappointment is a Process. One That You Can Master.

Dating disappointment is as difficult as it is inevitable.  But instead of wasting precious months (or years) responding to challenges in ways that keep love at bay, learn how to master the process so that you quickly move through your learning curve and into the arms of the one who is truly meant for you.

Here’s to you,