What I Learned From Dating Myself

Photographed by Rachel Cabitt.

I have a strong aversion to walking into places first.


It’s true — if I’m out with family or friends, I’ll always try to be the first to the door, so I can open it for the other people I’m with, forcing them to walk in ahead of me. It’s fucking weird, I know. But after spending a good deal of my 20s alone, I came to realise that my reluctance to step through doorways first stemmed from a bigger fear I used to have: being alone in a crowded room. Or worse, having people assume I was alone, and then feeling bad for me.

I know that this is ridiculous, because no one really notices (or cares) whether or not a person is by themselves at a bar, or in a restaurant. But, for a good part of my life, my singleness was something I tried desperately to hide. It was my least favorite feature about myself, so I tried to cover it up. Walking into a place behind another person signaled that I was there with them, so no one would make the mistake that I was waltzing into a social venue solo.

As I got older, my fear of being alone seeped into other parts of my life. If there happened to be a Friday night when all of my friends were busy, and I was stuck home by myself, I’d dissolve into a pool of tears. I have no friends! I’d wail. I’m never going to meet anyone if I’m always sitting at home on a Friday night!

I tried to calm this anxiety and fear by swiping on my dating apps, desperately trying to line up plans for nights when I knew I didn’t have anything going on. That, of course, made me feel even worse, which eventually made me decide (with some gentle prodding from my therapist) to ceremoniously delete my dating apps and take a dating hiatus.

Dating app burnout is a real thing, and I hit the wall hard. But the void that was left in my life — one that I used to fill with mindless dates with men whose faces started to blur together — was one of the scariest things I’d ever faced. My friends filled that hole most of the time. But every so often, there’d be a day when everyone had plans, and I’d be left to fend for myself. Once, after a friend turned me down after I invited her to go see an exhibit at the Metropolitan Museum of Art, she offhandedly suggested that I go alone. I almost burst out laughing. “That’s something friends and couples do,” I said. “I can’t go to something like that alone.” The thought of being seen standing by myself in a crowded museum was enough to make me panic.


So I tried to fill my days the best I could. I picked up a huge stack of books and started spending my down time reading alone in my apartment. I became a total hermit — I’d spend Friday nights reading, or scrolling through Tumblr, or watching Netflix. Eventually, I got to be okay with the idea of spending time alone — as long as no one could see me.

One day, I was flipping through the book How To Be Parisian Wherever You Are, and came across a passage called “Off The Radar.” It talks through a pretty romantic-sounding scene of a woman sitting alone in a café with her coffee. I started noticing that, throughout the book, there were little mentions of how French women don’t mind being alone sometimes, be it on park benches, at cafés, in bars, wherever. It sounded kind of nice — and kind of sexy, to be honest.

It was in that moment that I realised that being alone wasn’t just something I could tolerate; it could actually be kind of nice.

Now, I am a self-proclaimed Francophile. There is nothing I’d love more than to be a fabulous French woman, and I have absolutely zero shame in admitting that. So I thought that if being alone was trés Français, then dammit, I’d try it. (I’d like to take this opportunity to point out how absurd it is that a book romanticising French women was what inspired me to change my thinking, but at least I’m self-aware.)

I started off small. I grabbed a coffee and went on a walk by myself through Central Park, taking some time to sit on a park bench and look out over the Azalea Pond. I was surprised by how much I enjoyed myself, and just how nice it was to be alone with my thoughts for a while. I can do this, I thought. A few days later, on my walk home from the subway, I decided to pop into the bar a few doors down from me, order a vodka, and chat with the bartender. It was terrifying at first, but the vodka helped calm my nerves, and I was pleasantly surprised to find that the other people at the bar were friendly and chatty.


I started taking myself out on a regular basis, slowly testing my threshold for being alone. I saw the aforementioned Met exhibit by myself, and I found that I actually preferred going to museums solo. The biggest test, though, came one night when I decided to take myself out to an early dinner. I’d done this before, but I usually opted to sit at the bar so that I’d have people to talk to. But it was a particularly gorgeous night in early October, so this time I asked for a table for one outside. Not only would I be alone, but I’d be alone in plain view of every pedestrian who walked down that sidewalk. And being in New York, that meant a lot of people.

I sat down, ordered a glass of wine and some pasta, and then tried to relax. I’d brought a book, but instead of reading it, I sipped my wine and forced myself to people-watch. I expected people to stare at the girl eating alone on a Saturday night, but most people breezed right by without a second glance. And it was in that moment that I realised that being alone wasn’t just something I could tolerate; it could actually be kind of nice.

So now I try to date myself whenever I get the chance. I actually prefer to go to my neighbourhood bar alone now, because I’ve made friends with some of the bartenders and regulars there. I’ve had great conversations with random people on park benches, and have silently stood next to strangers in museums, staring at beautiful pieces of art. I do still feel lonely from time to time, but I’ve realised that I’m never really alone — there’s always someone around to strike up a conversation with. As for my aversion to walking into places first? I’m still working on it. But lately, if someone holds the door open for me, I find myself thanking them and walking in first.

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