Ask Jessie: How can I be more chill when it comes to dating?

Dear Jessie,

How can I be more chill when it comes to dating? I feel like I can’t get there AT ALL. For example, I’m trying to decide whether I should text this guy and it’s literally NOT A BIG DEAL AND I’M MAKING IT A THING.


Always Anxious

Dear always anxious,

First of all, you and I both know you should just text the guy. But what I’m actually hearing here is a fear of showing up as yourself in the dating sphere.

What if I’m too much? What if I text him too soon or too much or, or, or…??

That fear stems from the fear of being yourself as you start to date and it’s one that, if you listen to it, will keep you from finding the right kind of partner for you.

You should be your unfiltered self 100% of the time. This can feel SUPER uncomfortable if you’ve ever been a people pleaser, come from an emotionally unstable home, or been single for a long time.

It’s easy to fall into the mindset trap that you need to be on your best behavior to attract a mate.

But all that will get you is a mate who isn’t in love with the REAL you.

A friend once gave me the advice:

“Get mad early and often”

The idea is that it will set the standard for the relationship and how you expect to be treated. Not rocking the boat just sets you up for disappointment in the long-haul.

Your partner should bring the same level of understanding and eagerness to please as you do. If you need to keep your thoughts to yourself or censor your habits or personality to please someone else, well, both of you are going to be disappointed when your REAL personality comes to the surface.

I know it can be hard, especially if you’re a naturally anxious person (I have Generalized Anxiety Disorder, so believe me when I say, I FEEL YA), but don’t allow your fears to hijack your hope of finding someone who will love you exactly as you are.

For further reading on that, please visit one of my favorite articles ever written on anxiety and dating from Ask Polly over at The Cut: Am I too anxious to ever find love?

Happy texting!

Jessie Da Silva

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After months of largely crickets in my online business, I was able to do enough inner work that I could follow my true calling without fear. Once I snapped into the right mindset and habits, the money began to flow effortlessly. And now I'm ready to teach you to do that, too.

Jessie Da Silva

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