I am no expert but I’m pretty sure I’m a bit heartbroken at the moment. I didn’t think I would be. I actually thought I had gone through this incredibly brave, self-discovering Eat Pray Love kind of journey away from a relationship that ended this summer. As the autumn leaves fall and I can’t stop playing the “Indie Makeout” jams on my Songza playlist, I am painfully aware that I am currently wallowing.

We hadn’t been dating long, but it was instantly a very deep and real connection. The triumph of our busy schedules had been a planned weekend in Chicago – a romantic getaway that would feed our souls and our love. It would give us a chance to escape the everyday grind and discover a new place, hand-in-hand. As an artist, I would plan the theatre excursions; as a total foodie, he would make all the dinner reservations. We had planned this great trip for the end of October but well before that weekend arrived, we were parting ways, returning borrowed sweaters and books.

I was so smart and did everything right after we dissolved our union. I channelled my energy into work, creative projects, and my passion for running. The October date pencilled in as “Chicago weekend” sat there like a neglected pet, staring at me expectantly from my open desk calendar. I would have just erased it but every time I thought about rubbing the marks into faint etches, it felt like I was grinding down a promise to myself. To be fair, I did have the desire to go to Chicago before him and just because he had been a part of its inception didn’t mean it couldn’t live on beyond him, even if it meant going alone.

I have two great girlfriends. They’re the kind of women that must get post-breakup calls from their collection of friends all the time because they are great at dispensing that “You do you, girl!” kind of advice. It is easy to criticize, but when in the throes of panic-attack-level crying intermingled with sharp sobbing inhalations, that advice feels like a tight armour of love protecting your weepy, heaving chest from the world. So, I obviously called them and started crying, and they obviously said, “You do you in Chicago, girl.” It was then, through a teary, snot-filled sob that I said, “You guys are the best,” and booked my ticket to Chicago.

I didn’t think about my ex. I didn’t try to call or text to let him know what I was doing. It was my trip now.

Travelling solo has its perks, best of which is that you get to do everything you want, whenever you want, with no compromising. I touched down in the windy city and, despite a few travelling hiccups, I felt like a strutting Carly Simon lyric, bold and in charge. I saw great theatre that I know my ex would have groaned through. I even explored the subway system, popping up in different neighborhoods, knowing my ex would have wanted to take a direct Uber.

I did everything on my own terms. I wandered through the city, going into coffee shops, taking pictures of landmarks, and talking to people that stopped me on the street. (Okay, it was just one kinda creepy FedEx driver that gave me his business card – but it made me feel like Mary Tyler Moore throwing her hat up in the air, so it still counts.)

On my Saturday night in Chicago, I was down at Navy Pier to see a show, and I had some time to kill so I figured I’d treat myself to a nice dinner. I found the fanciest restaurant within walking distance and asked for a table. A bit of background here, I hate going to restaurants alone – I never do it. To me it feels like advertising to the world that you are super single and clearly don’t even have one friend that is hungry enough to spend time with you. But in the spirit of getting over things, I went in and bravely sat at my table set for one.

At first it was fine, then it felt great having white linen on the tables, my glass of Sauvignon, and a basket of bread – who could find fault in that? I sat sipping my wine, looking out at the pier, noticing the other couples, older couples mostly, ten or fifteen years my senior. I watched them interact: some flirty, some more tired but still friendly, some downright uncommunicative with each other. I watched them because I guess it was easier than looking at the empty chair that sat across from me. In that moment, the armour of love protecting me shattered into tiny metallic projectiles, spraying outwards in slow motion. I finally missed him.

I looked at the menu and knew what appetizer he’d be gunning for me to try, or the entree he’d order and oblige my stealing half of it. I recalled the way he’d let me trade wine glasses with him when what I’d ordered was too potent for my palate. The restaurant is what he’d have loved the most, yet he would have compromised his singular enjoyment of the whole experience to share it with me.

I ate slowly and I’m sure I drove my server crazy looking around the room so much. By the manner in which he continually kept dashing over to me, I assume my eyes looked like that of a panicked, drowning woman scanning the horizon for her lifeguard. “No no, I’m fine sir, thank you, just lonely as fuck!”

Upon my return to Chicago Midway Airport, I felt like the kind of adult so experienced at busy business travelling, taking just a carry-on, walking briskly through the lounge shouting into their cell, “I’m five away from the gate but I’ll call you when we land.” I felt busy and important, even if the only alert on my phone was a push notification for updated emojis.

I don’t regret my relationship with my ex and I don’t regret our parting ways. I know that this is part of the natural grieving process that just happens post-breakup. The Hollywood version of my trip would be: I go to Chicago, come to learn I am my own woman and return home a better version of myself. Another possibility: I go to Chicago, focus on being my own woman, but pull a cute Emma Stone ‘clumsy’ fall where a Ryan Gosling type catches me. We then open up a record shop and call it a Heart Beats ‘cause we’re so in love. In my real life though, it’s just been another shift in the greater movement; saying goodbye to the shared life I had with someone special.