Why You Need to be Messing Up with Dating

Do you lie awake at night after an interaction with a date analyzing the play-by-play of what happened, trying to anticipate your next move... and then his…?

I’ve been there. 

It feels so scary when you are in a new connection... You want to know how it’s going to end… 

Will he be the one? 

Does he like you? 

Should you have said that joke? …was that a pity laugh? … eek. 

You may be familiar with this song and dance. 

The whole process of dating feels vulnerable and out of your control. 

And it kind of is… 

You can’t force love. 

And yet, it’s so easy to get caught in this habit of worry… somehow it seems like part of the romance...

But what if the point of dating were actually to “mess up”? 

What I mean is relationships take skills… practice… to get to a level where you are sustaining a healthy connection with an intimate partner. 

Unfortunately, you don’t typically start there (or at least, I didn’t).

It’s like the Olympics... 

Those athletes have been practicing for a long time.

It’s something they’ve mastered… they could do it in their sleep… on an “off” day… blindfolded... and look effortless. 

Luckily, we aren’t being drafted to the Olympics tomorrow... it’s totally possible to learn something new- and it’s NEVER too late.

But we don’t want to wait until we are in the Olympics to realize we don’t know how to swim.

So starting where you are right now is actually the best place to start… even if you feel like you’re way behind.

The truth is, we’re on at different stages of our progress and we have innate gifts that come naturally to us that we lend to others in the training room, as they do for us, so we can all get more skillful.

Along the way, I’ve noticed this super seductive belief that will make it more challenging however- the “I’m more mature than this” belief that can cause us to miss out on all the juicy experiences and awareness we need to actually grow up. 

This belief keeps us as spectators.

It keeps us trying to think your way through something versus feeling your way through… conceptually understanding something versus practicing it… and, in my experience, you actually go faster using both. 

I’ll admit, I let this one seduce me for years.

I was quite proficient at lackluster (or, better yet, embarrassingly unhealthy) connecting skills and the need to “get it right” kept me stuck behaving in ways that are altogether not helpful until I started to practice how to do it differently. 

I felt awkward and clumsy tripping over my words- and I still do sometimes.

You see, the skills we really need- courage, vulnerability, resilience, self-acceptance, emotional regulation- take conscious effort but lay the foundation for something that lasts.

It’s the long game you’re playing here and it takes experience to gain wisdom.

If your goal is to get a second date or to have him like you, you will constantly be singing and dancing… and anxious. 

But to approach dating with the intention to “mess up”... wow that might just be revolutionary. 

I’m not saying you’re intentionally mean or playing with peoples’ hearts here… you’re only “job” is to practice being as honest as you’re capable of at this moment in time... 

We don’t get to control how the game ends but we are in charge of how we play.

If you get a second date, you get to practice again and maybe you go a little deeper and see how that feels to expose your heart to someone new. 

And I’m wondering how would you feel- and show up- if you saw each date as an opportunity to stop the song and dance and instead to practice speaking your truth? 

You’re building your muscle memory, retraining your heart muscle… for more intimacy. 

Not like the Olympics, but in a couch to 5k way… do able.  

Take away the expectation that this has to be something more than practice and see how you sleep at night.

You can start small in sharing your experience… instead of talking about the weather, talk about how you experience the weather- how the sun feels on your face, how the rain makes you want to dance, how the wind feels cool on your skin.

You can practice saying, “no”, or “actually, I prefer…” or “I feel uncomfortable right now”. 

Or what if you got so good at saying, “I’m struggling with X, will you help me?”... and actually got support? 

How would that feel? 

What I suspect is that you may actually get closer to finding the person of your dreams, feel more confident, and maybe even… have fun getting “back in the game”. 

I’d love to hear what you learn from practicing!