This Is Your Sign to Date Yourself

by Keira Johannson


design by Michelle Leung


I can still remember the first date I ever went on. It was to the local skating rink and I wore my favourite burgundy long sleeve with buttons on the front, the top one unattached – hoping to impress the middle school boy who I had grown an intense liking for. For years I had been romanticizing what my first date would look like: what I would wear, what I would do. But the thing my mind was focused on the most was what the other person would think of me. I had almost been programmed to feel the need to impress, to be liked, and to not disappoint. So two weeks later, when that same middle school boy decided he was bored with me, of course, my thirteen-year-old self became heartbroken.


Growing up, it was undeniable that every TV show, movie, or book that I consumed gave the main character a goal of being in a relationship with another person. And only after they fell in love would they be happy. It wouldn’t be until about five years later that I discovered that they had it all wrong – that the most important relationship is not with another person, but with yourself.


Despite my boy crazy phase in middle school, for my entire life, I have been independent – finding contentment in my quiet solitude. Obviously, there were moments when I longed to receive a bouquet of red roses on Valentine’s Day or share an intimate kiss to ring in the New Year; however, I learned to enjoy those occasions even when I had to celebrate with just myself. There is no shame in going to the supermarket and buying flowers alone or entering a restaurant and telling the host “table for one.” In fact, one of my favourite monthly rituals is taking myself out for lunch, just me, to the restaurant of my choosing, on my own schedule. There’s no pressure to wear the right outfit or stress about who will take the bill at the end of the meal – the only person I want to impress is myself and in this scenario, the act of treating myself to a nice meal is simply enough.



I have had my fair share of self-esteem issues and it took a long time to get to a place where I felt truly comfortable with who I am. In middle school when I went on that first date, it was with another person – my thoughts were always consumed by theirs. What are they thinking about me? What if I say the wrong thing? Do they even like me? These were all questions that filled my scattered brain. These thoughts followed me into high school like the bright moon on a drive home – even when I thought I lost sight of them, they managed to find a way to present themselves again – stumbling into those first interactions with strangers and even friends.


The best act of self-love (in my opinion) is devoting an entire day to celebrating you. And I’m talking about something other than your annual birthday. Oftentimes, on social media, we will see “happy boyfriend/girlfriend day” posts but rarely is there any talk about celebrating yourself. I find this absurd. Contrary to what people might say, being selfish is not always a bad thing. My mom always taught me to put myself at the top of my to-do list. As someone who tends to put others before me, this can be very difficult but it is by far one of the most valuable lessons I have ever learned. What started out as monthly self-care rituals have transitioned to a weekly habit where I spend an entire day doing the things that I love, with just myself. Not only is it good practice for being independent, but taking yourself out on a date also helps your inner confidence too.



The first self-date I ever went on was on the day I got my driver's license. April 22 – I’ll never forget it. It was the perfect spring day: warm enough to wear shorts but not too warm that your legs would stick onto the leather car seats. I drove myself to my favourite spot in my small city; a lake surrounded by tall evergreens and snow-capped mountain peaks. I ended up walking around the entire lake, listening to the wind’s soft sway and the music of the birds’ chirps. I had brought a bag full of art supplies and books with me, found a spot on the dock to lay my blanket, and began to paint and write and read. Art was always something I enjoyed doing by myself – being alone gave me the opportunity to truly reflect and feel at peace. Afternoon hikes in the sun then turned into coffee shop dates with an iced chai or spending hours searching the bookshop shelves for my newest read – all the things I loved to do and because I didn’t have anyone to join me, I did them by myself. It became my favourite part of the day. I would go on evening bike rides, indulge in a double scoop cone of cookie dough ice cream, and bathe under the sun with my toes in the sand.



Ultimately, when faced with the solitude I tried for years to avoid, I learned to become the person I was searching for – the person I could laugh with, cry with, talk with. The person I could turn to when every other message or phone call was left unopened. I could always rely on myself to show me a good time. The most important and the most long-term relationship we will ever have is the one with ourselves – engaging in activities alone, valuing our thoughts, respecting and taking care of ourselves, knowing what our boundaries are – all the things that should be celebrated instead of avoided. Even when on a date with another person, try and focus on what you think about them and not the other way around. Do you like them? Do they compliment the qualities you like in yourself? Do they challenge you to become a better person? And if all else fails – if you’re not a good match or the date doesn’t go well, remember that you can always make the next one better by making it with you. Here are some ideas that I would recommend for a good time: