Lessons Learned From An Awkward Date

Dating has taught me so many lessons, one of the most important being to share and communicate authentically and fully. I love all my dimensions, and the right partner will love all my dimensions too.

Last week I went on a date that derailed. There was 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. There’s a lesson in everything. 

To give you a little context, my dating life is important to me right now. I feel ready to take on the world with someone else, and I’m clear on what I want in a partner.

About a year and a half ago, my decade-long relationship came to an end. Being with one person all through my 20s meant I had never dated.

A little while after my breakup, before diving into dating, I met a man I ended up falling in love with. It wasn’t in the stars at the time, and that experience made me immediately realize that I needed to take a step back. I needed to not focus on who he needed to be, but rather who I needed to be to align with my vision for partnership.

So I decided I would go on 100 dates, a good sample size for getting clarity. Side note: There was no attachment to that number and I was open to meeting someone amazing along the way that would end the 100 dates adventure. 

It turns out, 100 dates will teach you a lot about yourself… My communication, self-worth, confidence, trust, intuition, and connection to myself and my purpose have been upgraded in massive ways. Which brings us to my recent misadventure that I share in my new podcast She [Out]takes the World.

This podcast is #notthehighlightreel. It’s the raw, wild, messy, beautiful journey of a powerful woman entrepreneur. Life and business lessons are so blended, and that’s why I’m choosing to share a different side of me with you. We are multi-dimensional beings, and I’m clear that opening my heart to you in this way, even though it’s a little terrifying, is how I can be of highest service right now.

Listen to the latest episode here:


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 just stay present.

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 something and unlocked a beautiful little piece of myself I didn’t know yet. That opportunity is available in every interaction we have with another person, whether on a date or at the grocery store or with a client.

If you want to hear more about this story and tune into the wild, beautiful, humbling behind-the-scenes of my life and business, tune into my channel on Anchor right here (where you can reply to me using voice notes and be featured on the podcast!), and follow me on Instagram. You can also subscribe to the podcast on iTunes or Google.

Now, I turn the microphone over to YOU:

What’s your biggest takeaway from my story?

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

Tag me, send me voice notes on Anchor, or email me at dearnatalie@shetakesontheworld.com. It’s always so amazing to hear from you, and I read everything. <3

Remember this: the pursuit of authenticity, while it can sometimes feel awkward, is always worthwhile.

Be yourself, and the right people will (eventually) find you. 



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