Dear Preskott*, my first in so many ways. First love is probably too generous but as my first boyfriend, you’ll always hold a special place in my heart. You were older and so much cooler than I thought I could be. I'd barely kissed a boy and somehow you were into me. They said you were a player, maybe I wanted to be played. I know now you weren’t always kind, once telling me the acne on my back meant I’d be horribly hirsute in later life. This hasn’t come to pass. I can still see those chunky highlights, “diamond” earrings, smell the mix of cologne and cigarette smoke. I remember how I lost my virginity to you while the Grammys played in the background. Céline Dion was having mic problems, I was having flexibility issues. I made you wear that powder blue baseball hat, turned backwards. It helped fulfill all the straight boy fantasies that would disgust me today, but in that moment it was hot as hell. You proceeded to cheat on me with my nemesis, whose spectre I'd fought since high school, first day. Callum, tall and willowy, pink skinned and self-possessed with that perfectly straight statue’s nose, everything I couldn’t be. This betrayal gave me a complex that went on for years, might still be going on. Last I heard you married a man, had kids. You’re probably a good dad. But maybe try not to make fun of their bacne. I still wonder why your name was spelt with that ‘k’...
Dear Jack, baby you dodged a bullet. Though it probably didn’t feel that way at the time. There was so much going on in your life and you still picked up, moved two provinces at my urging. I can admit now I was scared, didn’t want to go alone. I needed a steadying presence in my life and you were happy to provide. When I gained confidence in the new city that need ran out and I tossed you aside, for that I’m sorry. No other relationship has soured so quickly, and no other break up has felt quite as concentrated in its implosion. I still can’t listen to those yearning first notes of Hero and Leander from Myths and Hymns without seeing your sweet snaggle-toothed smile, without thinking how I shut you out, how I couldn't support you in your family difficulty. I cried and cried to that album, convinced every word was about us, but really about me because that's as far as I could see. The way I sobbed and sang in our empty apartment by the docks, "my lighthouse on the shoreline, my passion on this lonely sea..." The way I stared across the harbour singing, “my loving you was meant to be...” Ludicrous now, but at the time, oh at the time… I know we’re good now - you sent me that note. It was lovely to hear you stayed in the city on the island and found a life that leaves you fulfilled.
Dear Matthew, you got me at my worst. Maybe we should’ve known from the way we started it would be a rough ride. I went home with you the same night I broke up with my boyfriend who’d moved across the mountains for me, the same night I’d run back and forth across my building alternating makeout sesh with you and a classmate, the same night I kicked everyone out of my house in a rage. We had stars in our eyes, blind to everything that wasn't us. That's never a good sign. You were the first person I ever told my biggest secret. I remember crying in your arms on that pile of pillows in the acting studio. You cried too. My concept of time has always been junk, but it feels like only a little while after that you proposed. Or was it me? Lying in bed together all giggly, somehow we decided we’d lived enough life on our own. Everything about you made sense. In the morning that was terrifying. My plate was already full of terrible memories and I’ve never been good at accepting good in my life. I spent the next few months dodging your questions. I also spent those months spiralling further and further into depression. The day you found me in a heap on the floor, crying uncontrollably, totally unable to accept comfort is still the deepest sadness I’ve felt in my adult life. But you sat by me, waiting. You waited a lot. We broke up and got back together so many times, we lost count. Do you consider that time a waste? I still remember your kisses and hugs, the way our bodies entwined throughout the night. I wonder, if I hadn’t been so off the rails, would we have survived? Last we spoke you’d been with the same guy for awhile, possibly heading toward marriage. I know that’s what you always wanted, to settle down, have kids. If my madness hadn’t ruined us, that probably would have. I hate to admit, I'd probably still make out with you.
Dear Sean, your shine persists. We had our problems, I know, but our relationship felt stable in a way no other has. Maybe it was my year of sobriety, maybe it was being stuck in the Prairies… really though, I think it was you. Your caring spirit was like none I had encountered before. Your non-judgemental kindness surprising me from the start. Though we had a deadline, nesting with you was easy. I remember how you'd stay up with me and my unsettled mind despite having school the next day, I remember how we’d sit and leaf through your giant atlas while getting baked, I remember how you would give me space to disappear into my writing for hours on end, then make us an amazing meal. I ate like a king in those days - I’ve never been so chunky in my life. You were even willing to give non-monogamy a try. Something about the fact you couldn't go through with it was terribly romantic. When you proposed, though it made no sense, I accepted. It was probably unfair to do so. I didn’t want you to give up on moving to Asia, I didn’t want to compromise on moving to Toronto. You used to say it didn’t matter that our paths were divergent, we could make it work. Maybe I was cynical, less prone to Big Romance. All I know is that everything that had come before taught me to be cautious, taught me that really loving someone sometimes means letting them go. We were no longer engaged. We moved apart. A while back when we messaged each other about I don’t know what you said you’d move here in a second… I actually considered it. It's still a bad idea.
Dear Kyle, I was blindsided by your jawline. I suppose I’d had too much stability in my life for too long and I needed to be upended. I broke a cardinal rule for you and probably deserved exactly what I got. But you were so charming and handsome and broad-shouldered and had that long hair and those lips. On our first date when you drove us out to the beach and we made out on that log and laid in the grass under the stars, I knew I’d been hooked. When you picked a small flower and gave it to me with that smile; when you pretended to look over your shoulder in the car and instead gave me a quick kiss… boy, I could see all the moves. I could see how you were playing me. But it didn’t matter. I’d already decided I’d give in and let myself Feel. To my dismay, I became that kid who waited by the phone, who thought about you always. I could see myself careening toward that wall and let myself crash right in - I’ve always had a self-destructive streak. Then that day when you visited between rehearsal and work and we napped in the sun, I came to my senses. Somehow in that afternoon light, the heat, I faced the truth: I was more into you than you were into me and that simply wouldn't do. Our last night together, at that party where my phone got stolen, your friends kept asking, as if we were in high school if I “liked you," if I "wanted to be your boyfriend." One of them even pulled me into a room and grilled me on my intentions. Yes, I’d let myself Feel, but I knew it wasn’t serious, I knew we weren’t meant to be. How could I make it work with someone I only made out with to avoid listening to their stories? We went back to your place and the heat had been so dispersed I could barely put your dick in my mouth. We stopped texting after that night. Then you moved away. Your current boyfriend recently liked a post of mine on Instagram, then followed and unfollowed. Maybe he was upset I hadn’t followed back. Maybe he knew we once had a thing.
Dear Charles, I had to take a pause before I wrote to you. Not because the feelings are hard to deal with but because you’re the last, so far. There have been flings, one night things since you. But nothing serious. We weren't together for a long time but you taught me a lot. Or maybe it’s best to say, you finalized a lot. I was finally able to admit after you that, despite wanting something long-term, I really, really don’t want monogamy, I don’t want kids, I don’t want to settle down in the traditional ways people settle down. It wasn’t easy to admit this. I remember looking through your Insta after you asked me to get a soda and visit the cherry blossoms. There was a photo of you smiling in your fave flannel, holding a baby. It reeked of sweetness and I hope it's not offensive to say, but I swear I straight up grew ovaries and started ovulating on that day. I remember lying in the grass in High Park and talking about whether or not we saw kids in our futures and I lied. I lied because I thought I’d be more attractive to you if I said I did. Because that’s what all the nice boys - the ones worth anything long term - seemed to desire. I made every effort to be the kind of man I thought you wanted. Pretty sure I tried to become my ex, Sean. But very few people can be that good. My mom had come to visit while you had a show on. I was making you a gift as she watched. She shook her head said I was sweet, that I fall too hard, that I'm prone to exposing too much of myself for those I deem worthy. I scoffed. But when it took you three days to acknowledge the gift, I realized she was probably right. I was reliving a pattern I’d lived several times before. Despite the self-centeredness of youth, you were a sweet, kind boy who checked a lot of the boxes we're supposed to want checked. Maybe I thought I could change for you. But I’m not that guy. Not really. Someone told me you’ve been with the same guy for the last few years. I’ll admit I think about you often, your name is everywhere in the city and we covered the most area in our wanderings. The thoughts are warm, with no bitterness. How could there be? Our breakup inspired me to write a whole play, and that play set me on the path I’ve been travelling for the last few years. I wonder sometimes why I don’t see you in more things, conveniently forgetting how little theatre I actually see, then tell myself I should write something for you. But, despite those previously mentioned warm feelings, I don’t think I’ll ever really trust you. Doesn't help that you think Beyoncé is only so-so (!) but you stan Taylor Swift hard. I'll see you around again, no doubt. The city is too small not to. I'm pretty sure I'll be nice. If I'm not, say something nice about Queen Bey and I'll probably warm up.
Dear Future Love, as you can probably tell from the above, I’m a bit of a mess. I’ll probably fall too hard for you too quickly and then proceed to ignore you when I get into my fits of creativity. I still don’t quite know how to be part of a family or how to not be socially awkward. But maybe, like me, you’ll think it’s okay for us to keep our friend circles separate so my inability to have meaningless conversation in large groups won't be an issue. Or maybe, like me, you often think you’re an alien left behind to observe and we can loom on the edge of parties, quietly judging or praising sartorial choices. I’m still a terrible cook, but I don’t mind baking. If you cook but hate to bake, we’re equally matched. If you also bake, I’m sorry my dear but you are up for elimination. Not really. I’m totally down to make muffins together as long as you’re not one of those non-allergy gluten-free crazies. I’m prone to overly chaotic workflow, I’ll never know where anything is. I’ll want to talk over wine about movies and TV shows until all hours of the night. I'll want to get baked and drag you to shitty action movies in 3D. I love celebrity gossip, will always want to watch the Oscar's red carpet, and will probably hush you when Nicole Kidman or Angelina Jolie show up. I still use too many words to say something simple causing me to forget what I’ve said two minutes before. Somehow, despite this terrible memory, I will remember many things you say and then use them against you at a later date. I’ve retained my love of cuddling and getting all tangled up in each other, but when it’s time to sleep, I’ll probably move as far from you as possible. This isn’t because I’m mad or suddenly don’t like you (most of the time). I’ve lost my disgust for feet so I’ll be willing to give you foot rubs. In fact, I’ll probably rub you a lot. Your cheek, your head, your back - it’s a thing. I also give random squeezes. Usually of the bicep or thigh. I hope you’ll be comfortable in your femininity and accepting of mine, I hope you’re able to hold hands in public, and okay when I put my head on your shoulder at the movies. I hope you’re ambitious and creative (just don’t be an actor) and that you teach me a few things. Like where to find good vintage sweaters that don’t smell like old men or where to get the best deal on rhinestones. I hope the people who came before me were as wonderful as those who came before you. These gents taught me a lot and I'm grateful to them. Maybe, if things don't last between us, Future Love, you'll make it onto this list. Or maybe our story will be so long and full of stuff it'll take a whole book. Oh, that's another thing: if you date me you better be okay with showing up in my writing, 'cause it's already happening. Kisses!
*Names have been changed.