The Not Chill Way I Approach Dating Because I Give A Damn

There’s been a few sparks in the last year of dating. The butterfly moments where you smile knowingly to yourself and music lyrics hit just a little different. At my peak Capricorn/corporate self, I created a flow chart ranking the men based on various strengths and attraction levels. I kept it updated. Weekly. Without a doubt, I was determined to post-it-note my name and number to every potential coffee shop romance encounter I had. No man was safe, Alissa was on the prowl to make connections, and learn what she likes (and dislikes) (in both men and alcohol).

As the temperature dropped, so did my intensity. It’s easy to lose yourself in the dating world. So I took a few months to write out my reflections and learnings. Some are current, some are part and some are in-between.

But the biggest thing I learned about myself?

I’m not chill.

I give a damn. In fact I want to give a damn.

I don’t vibe with those who don’t want to act like they give one.

I’m not chill and never will be.

I Think Being Chill Holds Us Back in Dating (And a reminder: I am not a chill person)

One of the worst parts of current dating is the hurt of not wanting to be the one who cares. There’s a sort of je ne sais quoi to seeing who could care less. Are they just chill or do they not care? The question after every vague response as you try to create a plan to you know, actually schedule a date. On a dating app. A shocking outcome that no one would expect. Don’t show you were excited for plans. Oh and don’t communicate a miscommunication was a letdown. Make it as easy to walk away and be very clear you couldn’t care less.

I think this goes along with the casualization of everything. As a planner, in a city that requires strong foresight into what I want for dinner in six weeks so I can make a reservation, I do not vibe with the chillness. Dressing up is fun! Having multiple destinations in one night is fun! Showing appreciation of someone who wants to create a memorable experience is the new vibe!

This is the world according to Alissa, but I think this is what all of this means: When dating, we need a shield to maintain our power. Being chill and demonstrating how little we care helps us protect our vulnerability so we are seen as strong and unbreakable. (Yet we are all trying to meet and find someone, but instead of it bonding, it creates a heightened sense of self-preservation.

Anyway, now that I’ve very casually and very chill level set with you, let’s move on to vulnerability.

I’ve grown to *almost* dread the feeling of a wonderful date. Because what goes up must come down. Right? And, I’ve learned, after a string of really great first dates, many times it stays down.

Queen Taylor says it best, “You know how scared I am of elevators, Never trust it if it rises fast, It can’t last.”

Once I was excited to text or call my friends to immediately provide updates.

After about the third great first date, I started to feel really vulnerable. And aware that I was the friend who was always excited about some new person.

Cringe.

Creating a Dating Thesis

Last summer I decided to make a dating statement to help me figure out what I was actually seeking from someone or within myself. I’d never made a dating thesis before. I think it’s because I wasn’t aware of what I actually needed, much less wanted. Something needs to be able to be measured and bounced against as I look for what I want.

This dating thesis truly helped me sort through the confusing highs/lows, will they/won’t they and remain clear on what I wanted. Something casual? No. It took me a few tries to figure this out. Sometimes I was aware when someone was on the casual and consistent side, which I find to be the hardest to cut off.

Oh. In case you need to read this: just because something is there and consistent doesn’t mean it’s good or going towards something.

Check please.

What Energy Means I’m At My Best?

After the summer sparks faded into distant memories I turned towards analyzing why they felt a bit more sting-ey than previous encounters. I realized it was because I loved the energy the situations (not the people) brought out in me. It was relational and partnership energy. The kind that made me want to go out in a flash flood (literally) to get a cup of coffee for someone because I wanted to greet them with their favorite roast when they arrived.

Me in my best relational and partnership energy looks like a tenderness that I tuck away for most of life. A softness that is uncomfortable for me to demonstrate, but with a vulnerability that I want to explore and share and grow in. Just a few touches that makes someone cerebrally aware I’m listening and showing up with just a topping of thoughtfulness.

That’s me at my best. I like what’s been out in me this round. A softness. A care. The things I’ve tucked away because I’ve been afraid they’d show weakness. Fewer dates required me to prepare lists of questions. I wasn’t care less, I was careful, but vulnerable and lighter than before.

The Co-Authors We Invite into Our Lives

What I don’t love about dating and love is that it requires letting someone be a co-author. No longer a single author but a shared page that unites two different chapters, storylines, characters and plot twists. But! The more I think about this concept, the characters in our lives and stories, the more I realized it applies everywhere! Our friends are also co-authors, it just feels less vulnerable because there’s not an overt ask.

I don’t feel hesitation to show excitement about plans to my friends. They get calendar invites! Reminders! ‘Fit checks! I value my friendships even more than romantic ones, there’s no chill there. Yet somehow I didn’t feel the need mask it.

We’re always writing the chapters of our lives with someone. Consciously or subconsciously.

Just be what you want to be in dating. Like someone! Get excited about them! Get upset when they cancel plans (because it is rude and we need to stop letting people get away with it)! I hope you absolutely find yourself at the unhinged level of caring (in a healthy way) because the only way you find someone to care about is to actually start caring.