Que será, será
What a weekend of exploration in Chicago taught me about love + dating
He tried to kiss me and I dodged it.
As if his lips were the bullets in The Matrix. And moments later, we talked and laughed over deep dish pizza in Lou Malnoti’s. Que Será, Será played through the speakers of his Jeep as we rode back down Lake Shore Drive, and I knew we would never speak again.
I’ve modified my expectations many times, but always keep my hopes high.
And my visits to the dating world are fleeting. I jump in, I jump, I jump, and I jump right back out.
From dating intentionally with the end-goal in mind to just wanting a good time, I’m either not for them or they’re not for me, or we’re for each other for a while until we aren’t anymore and by the end of whatever has transpired I never remember for what I was hoping.
It’s like I made it all up. I made it what I wanted it to be instead of seeing it for what it was. I’m just tired. I just need a minute. I’ll jump back in next year, I always say.
We skipped the line at Three Dots and a Dash.
He picked me up from the docking location of the Chicago Architecture Tour and I was still high from the ride up and down the river highlighting views of the city at sunset. He filled my ears with compliments, and I sipped my oversized cocktail, gazing upward reading his lips as he spoke highly of my energy and the love I seem to have for creating purposefully.
My thoughts slipped to the few messages exchanged prior to this date being arranged, and his voice faded as I wondered how he knew enough to be so impressed.
Maybe it didn’t matter if he meant it. Maybe I just needed to hear it.
Finding him used to be a priority - different ages housed different milestones, and when I wasn’t married by 25 I said 30 would be nice but by 28, more than anything, I just wanted to be left alone.
My fleeting visits to the world of dating grew more scarce. I was too busy with myself to be with them. All my space was filled with all my things, there was no room for what would come with them.
I was living deep in my own world, focused on what I can control and leaving what is meant to be up to the powers that be which meant catching flights with no concerns for catching feelings.
But I still felt him there. He wasn’t at the forefront, but he was still in my mind. In my dreams. In one of my favorite visions of my high hopes for my life.
I was catfished but he was sweet.
He covered both our admission to the Observation Deck of the Willis (Sears) Tour, and captured decent content for me. If he had looked like his photos, I would have spent more time with him.
But he didn’t, so I didn’t.
Instead, I strolled along the Riverwalk solo and fully immersed in Summertime Chi. Seeing the people, the boats, feeling the energy, the music, I almost lost track of time. I took just a piece of the energy with me as I rushed back to the hotel to freshen up for dinner.
I just wanted to see. I just wanted to learn how to strike a balance between all the extremes.
Being open to being found while discovering myself. Being intentional but remaining detached. And being grounded in reality while still embracing the fantasy, because it exists. I just can’t let myself get lost in it.
He was late, and the sea bass was delicious.
My calabrian spritz was cold, and the conversation flowed over a delightful meal at Acanto.
He expressed earnest toward his profession, however there was an undertone of insecurities present. I don’t judge as we all have them, but how do I know I am capable of truly helping him with those? I’ve known the seat underneath me longer than I’ve known him, and I haven’t even finished my matcha gelato.
But we did stay in touch. And it might’ve had potential but that’s not enough. I’ve already learned my lesson there.
I flew in and danced atop the breezes of the Windy City ready to receive things for what they are, and my luggage for the two days was too small to bring back anything that didn’t fit.
And to end the final night, I stood amidst a sea of smiling eyes on Navy Pier, and allowed the fireworks to hypnotize and seize my mind.
Sometimes we’re meant to share a moment, sometimes we're meant to merge worlds. Not every connection is created to last, but they always provide something that is.
And I can be open to meeting him without seeking. He will find me when it’s time, and even then, I will keep myself in the spotlight of my mind. But I’ll make space for him beside me.
Que será, será.
-A
thanks for reading! if you’re more into the trip logistics than my love life lessons, check out this Chicago setlist. a curated list of cultural, social, and lifestyle recommendations for your trip to Chicago, IL.
