At the start of last summer, I made a commitment to myself to journal every day for an entire year. My intention was to write daily as a means to hold myself accountable, and to stay on top of my running thoughts instead of letting them get ahead of me. I had been a journaler since my childhood, back when it was still considered a diary and I used a nightlight under my bedsheet past my bedtime. Back then, my writings were incredibly honest and met the page without judgement, as I attempted to make sense of the world around me and wrote lists of ways for boys to fall in love with me (** see end of this article for actual images).
My Year of Journaling
As I embarked on my year-long journaling journey, I began to realize that what was once an unfiltered dumping and reorganizing of my thoughts, was now many pages of “I’m just not sure what to write about today,” or “I don’t feel like I need to write anything at all.” The average brain generates roughly 70 000 thoughts per day, spiralling and bouncing off the walls, yet when tasked to speak on any of them, I often came up short. My writings were less honest and less intentional, and became a sort of box-ticking each day.
On one desperate morning, I started a journal entry with “how are you today?”, as if I was being asked by someone else. I continued to ask a series of questions and closed my journal afterwards feeling as if I had just been on a date, uncovering things about myself I had never written, or realized. Instead of writing about what existed at the very front of my mind, I reframed my own act of journaling as an intentional way to get to know myself better.
I started going on dates with my thoughts, with my inner self.
Over the course of the last year, we have been through a lot together — my journal and I. We’ve weathered tear stains, food stains, and had entire pages ripped out. We’ve moved countries, been through one and a half breakups, torn an MCL, and turned down the job I once dreamed of. My journal has been a coming of age story, a comedy, a romance at times, and a horror at others.
And naturally, we have been on many, many dates.
We expend so much energy and effort when in the initial stages of dating someone new. We get ourselves ready, choose the right outfit, and calculate the perfect amount of travel time to show up desirably late. We sit across the table, asking questions and listening to their answers — their traumas, feelings, weird interests, and pet peeves.
What if instead, we go to dinner and a movie with our own thoughts and feelings, our own weird interests and pet peeves? What if we take our inner self on a date in the hopes of getting to know each other better?
This is my guide to taking yourself out (on paper).
Picking a spot and first-date jitters
To start, like any first date, you have to decide where to go. This can be on your couch, in your favourite coffee shop, by a body of water, or on the train ride home. Ideally, it is somewhere that you feel able to express yourself and write without fear of someone peering onto your page.
At the beginning of the date, you might feel nervous. It can be terrifying to face your thoughts. Fortunately, like any first-date jitters, they often fade after the first few minutes — once you’ve ordered a drink. Oftentimes, the hardest part is showing up. Committing to sitting across from yourself at the table is no small feat, although you may surprise yourself in how much you enjoy your own company.
I suggest starting simply. Icebreakers, if you will. “How are you today?” or “how have you been this past week?”. You are easing yourself into the process of unraveling. It takes time. You can show up for your date exhausted, barely able to form a sentence, or incredibly excited to meet who is sitting across from you.
As you grow more comfortable, you begin to share more about yourself.
You can introduce your family, friends, hobbies, and even indulge in stories about your irritating co-worker who you simply cannot stand. Introduce your book that is never-ending, the strange dream you had last week, the doctor’s appointment results you were so afraid of, and the gift that your mother got you for your birthday (I’m not sure why she ever assumed I was a size small?)
Intimate details and awkward silences
As you soften into your chair, relaxing your shoulders and unclenching your jaw, you slowly embark on the next phase of dating. The intimate details — how you’ve been feeling anxious some mornings, how you’re upset at your longterm friend who won’t return your texts, how you feel like you’re chasing after the world instead of riding its orbit. Ask questions to yourself, and allow questions to be asked of you in return (nobody likes a one-sided date). You likely won’t have all of the answers, you may not even understand the question. Perhaps scribble them into the margin, and return to them on another date.
There may be moments during the date that make you feel uncomfortable — awkward silences as you stare blankly at the page, not sure what to say next. Instead of filling the space, taking a sip of water, a break to the bathroom, or a quick trip to your Instagram feed, try sitting in the silence. In real dates and journal-dates alike, we often dread these moments, although they always pass.
Uncovering memories and the pressure to date “right”
While you continue to gently mine yourself, you may uncover memories that you didn’t realize were buried. When learning more about yourself, you’ll inevitably encounter the many parts of you that led you to the very table you now sit at. These pieces, like your never-ending book and strange dream, are valuable. They create the landscape of your identity, however unsettling they may be to face. Fortunately, you don’t have to share everything at once. These memories, like the unanswered questions, can be left scribbled in the margins for another date.
At the end of your date, you may feel as though you said too much (maybe you didn’t need to talk about your ex-boyfriend for three pages). Or, you may be frustrated by the way that you kept your guard up, the way that so many things were trapped at the tip of your tongue. Luckily, the pressure of dating “right” disappears when you are dating yourself. Whether you overflowed with embarrassing stories or barely got past the initial “how are you today?”, you can always recycle the pages and try again. There are plenty of other fish in the sea, and plenty of blank pages still waiting to be filled.
No matter how the date goes, you are bound to close the book knowing yourself a little bit better. And what a privilege that is — to get to know and understand yourself better. It is terrifying and tender, takes great self-awareness and confidence, and can feel like a bottomless excavation of your inner world. Yet still, you return. You meet yourself again on the page, and continue to chip away.
With every awkward silence, uncovered memory, and scribbled margin, you begin to realize that you are someone worth coming back to.
And who knows? You might even find yourself to be a great catch.





