What an awkward date taught me about love

About a week ago, I went on a date that completely derailed.

It was awkward, messy, and all around bad. There was even a moment or two I wished a door would appear out of nowhere just so I could run away.

And yet?

I’m glad it happened.

Because it reminded me: This is all part of the journey of taking on the world, and trying to find that one special person all at once.

To give you a little context, my dating life is something super important to me.

A little over a year ago, I left a decade-long relationship I’d been in since I was 20. That meant I’d never really “dated” up until that point. Sure, I’d been taken to dinner a few times by guys in my late teens, but when it came to really playing around and enjoying the experience of meeting new partners? I was a complete newbie.

Still, despite all my intentions to date around and “play the field” Shortly after the breakup, I met another man who I fell for hard… but it wasn’t in the stars for us.

That made me immediately realize that I needed to take a step back. I needed to, in typical Natalie fashion, play around and find out what I wanted through trying a lot of different things.

So I set a goal: I decided to go on 100 dates, and get a good sample size for figuring out what I want.

As it turns out, 100 dates will teach you a lot about yourself. I’ve learned more in the last year about how I go about human connection than ever before.

… Which brings us to my recent misadventure.

There we were on date #2.

Second dates are rare for me, by the way — but the first date with this man had gone so well, I was ready to dive in and see what happened!

We were strolling along the beach, having a pretty deep conversation about what we value in life and what excites us — which I love to do on dates.

I always seek those deeper, valuable human connections through conversations that go waaay beyond surface-level, typical dating stuff. (Sure, i’m open to hearing about where folks grew up and went to school, and what they love or hate about their jobs… but after that? I want to skip straight to the real stuff.)

The further we dug into the “real stuff”, the more excited I got.

And when I get excited like that? I start to move around a lot. I actually began to dance right there on the beach, just for fun!

… And let’s just say this man did NOT, care for “dancing Natalie”.

He seemed to like “business Natalie” quite a bit, but as soon as I started laughing and jumping around a little?

He sort of rolled his eyes, and got a concerned look on his face, saying his parents wouldn’t approve.

Wait, what?!

OK, now listen here buddy…

And just like that, I knew it was over. I think he did too.

Sure it was disappointing, but at the same time, I learned more about myself and what I need from another person.

I learned how crucial it is to show up authentically on dates — to take the risk of showing the person your whole self, because that is who you want them to fall in love with.

You don’t want to present a watered-down version of yourself for the long-term, only to catch your partner by surprise when all your wonderful weirdness eventually starts to shine through.

In my opinion? You should put that authentic weird out front, first.

Here’s why I’m sharing this story:

On this journey of 100 dates I’ve learned to lead with vulnerability — to show parts of myself that are difficult to show, because that is what is going to lead to the deepest, more valuable connection.

Dating is similar to business and branding in that way. And, just as in business, I’ve also learned to be unattached to a certain result, and let come what may.

This is one of the absolute hardest things to do, but the reality is: If you’re already thinking about the future? You’ve lost the opportunity to connect with the person in the present.

In every one of these dates I’ve learned about myself, and connected with new parts of who I am in all aspects of life.

Now I’m just excited for the journey to continue.

By the way — if you want to hear more about this story? Or just tune into the wild, beautiful, humbling, occasionally-shocking messiness that is my dating life?

Tune into my channel on Anchor right here (where you can reply to me using voice notes!), and follow me on Instagram.

Now, I turn the microphone over to YOU:

How have YOU found authentic love in your life — or is it even something you’re pursuing right now? How did it happen?

Do you have any hilarious (or romantic!) dating stories this is making you think of? What happened next? What did you learn?

So tag me, send me voice notes on Anchor, or email me at dearnatalie@shetakesontheworld.com. It’s always so amazing to hear from you. <3

But until then! Remember: the pursuit of authenticity, while it can sometimes feel awkward, is always worthwhile.

Be yourself, and the right people will (eventually) find you. That’s just the way the universe works.

I’ll see you next time.



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