10 Diary Entries I Never Wrote (But Wish I Had)

In celebration of our upcoming ten year anniversary we are publishing a Top 10 list by a carte blanche editor once a month. This month’s list is brought to you by Chalsley Taylor.

Like most writers, I journal. These days, however, my entries are pretty infrequent (and that’s a generous estimate). When I was young—younger—I journaled as if my life depended on it. In a way, it did depend on it. In every notebook I reigned supreme. Outside of those books I had little, if any, power over my day-to-day reality.

When I am feeling particularly brave, I’ll go back and flip through some of those books, and whether the experience leaves me amused, misty-eyed, or mortified, they always seem sort of incomplete. I think I now know why that is. Part of it is the fact that not everything that happened to me made the cut. Some things were too shameful, and some I just never took the time to ink. In my diary I performed myself to myself, and it all had to be just so. The other reason is that there were some adolescent landmarks I just never hit. (Too bad, so sad.)

What follows are the entries I wish I’d written: some real, some fictive. Names have been changed to protect my own hide.

1. The First Kiss
My first kiss was…unspectacular. Which is not a value judgment on the boy who gave it to me; it was no failing of his. It was the circumstance: a game of truth or dare atop a jungle gym we’d all long outgrown. Jason was instructed to kiss me “on the lips”—so romantic.

Dear Diary: Today I got my first kiss but it was pretty boring.Teresa dared Jason to kiss me on the lips. Dorito breath Jason!!! I took out my gum and faced him and kept my mouth closed and he puckered his lips really tight and closed his eyes. It was quick and didn’t feel like anything. After he pulled away I put my gum back in my mouth and Teresa and everyone burst out laughing and yelled “DRYYY!!!” Jason looked embarrassed. I just wasn’t done with my gum.

2. The First Crime Spree
My early thefts went unrecorded. At the time, I didn’t see my little habit as criminal; it was just a function of my ongoing quest for candy. When I was 8 or 9, my grandmother’s bedroom was next to mine and, like most grandmothers, she kept sweets around. Not always the ones I liked, mind you, but the inconsistent quality of my haul was no deterrent. Real “Fuzzy Peaches” or no-name brand “peach slices,” I had to have them. While my grandmother was out, or downstairs in the kitchen, I would crawl (all stealth) into her room and gently pry open all the candy caches I knew of. The top dresser drawer always rendered a profit. I did this almost daily for months, and for a while I was pretty sure I was getting away with it.

Dear Diary: Today Granny told Aunty Phyllis that I’m a “klepto” and I think she knows I’ve been taking her movie candies so I guess I have to stop. It’s ok though. Lately all she’s had in there are those weird candies that look like chocolate chips except they’re different milky colours and don’t taste like chocolate AT ALL.

3. The Second Crime Spree
My next bout of law breaking was years later, though my goal was no different: steal all the candy. It was sixth grade and kids my age were not permitted to leave school property during lunch without written permission. This wasn’t hard to obtain for most, but my own mom refused me the holy note that would let me step beyond the field and onto the catwalk that led out to the street. Every day I watched and I moped—until I realized that no one was really keeping tabs on me while I skulked around the borderlands of the field. As long as I was back in time for the bell, no adult would be the wiser. Except I had no money—“allowance” was a foreign concept in our house. I could sit in the pizza place, but I couldn’t buy pizza. I could, however, troll the over-crowded and poorly laid out convenience store with an equally crafty accomplice, and slip whatever I pleased into a plastic shopping bag.

Dear Diary: I got a bunch of stuff with Jenny again today at lunch. Can you believe that place only has ONE camera and it’s pointed at the REGISTER?! Soooo dumb, like, they don’t even have mirrors at the back and there’s only ever one guy in there. Anna still says I “shouldn’t be doing that stuff with Jenny” and it kind of makes me feel guilty but I just love Fun Dip so much!

4. The Fist Fight
I’m a pretty non-confrontational person by nature and a pretty un-athletic one by choice, so I’ve never been the fighting type; I’m more the sit-and-fume-in-silence-while-scribbling-about-how-awful-you-are type. I’m mostly OK with that, but some small part of me can’t help but think I’ve missed the boat. Getting into an all-out, throw-down brawl is kind of frowned upon once you get out of high school, no matter what the case may be on The Real World. If I had been in a fist fight I probably (definitely) would have lost it, but I’m confident that I would have at least come away with a good handful of my opponent’s hair. I’m nothing if not well-taloned.

Dear Diary: Today in gym class Courtney called me Roger Rabbit for the bazillionth time and I totally flipped on her because I was in the worst. mood. ever. (gym class + a visit from aunt flo = a very angry me) If I was paler I’d probably have bruises all over.

5. The Slow Dance
In the seventh grade, everyone but me had rhythm. In a setting where choreographed dances were acceptable class assignments, this was a real problem for me. For my first seventh grade dance I volunteered to man (girl-man) the concession stand, a little kitchenette type room with a window over-looking the dance-floor. I was in my glory at that counter, doling out cans of pop and mini chip bags. No awkward two-stepping for me, no trying to nonchalantly watch my own body, to sync it with the beat of that Ludacris song booming out of the sound system (whatever Ludacris song you just thought of, yes, that one). In my little room, I feared nothing. Then a slow song came on, and I distinctly heard someone shout “Where’s Chalsley!”

Dear Diary: I almost managed to avoid dancing at all, but Jessica and them dragged me out of the kitchen and MADE me slow dance with Derrick. Like, I know we’re going out and whatever, but it was SO EMBARRASSING!!! I didn’t know what to do, I rested my fingers on his shoulders and he put his on my waist and we kind of waddled slowly like robots. Jessica just HAD to point out how stiff we were and ask why we were standing so far apart. She couldn’t stop laughing. Worst. All the other couples in class were, like, hug-dancing, and hardly even moving at all, so I guess that’s what a slow-dance is supposed to look like? Ugh I still don’t even know.

6. The Boat Cruise
The plan for my school’s eight grade grad celebration was to grace the stage in our glittery gowns and ironed suits, stuff our faces at a nearby restaurant, then head down to the harbour front for a romantic cruise on Lake Ontario. Unfortunately I never attended grad at all, feigning illness to avoid facing a recently estranged friend. It seems so silly now, of course, but at the time, a night out sans her company was a torture too great to bear. So, through no fault but my own, I missed out. On the plus side, from all accounts the cruise was less than we’d hoped for.

Dear Diary: Just got home from the boat cruise and I’m still shivering. We weren’t allowed to turn up the music and the lake smelled nasty. Greg pretended to hold Teresa’s phone off the side and then he dropped it of course and she attacked him and we all had to get off early. PS, the food at Hot House was gross, why do so many people eat there?

7. The Summer Fling
I never had one of these, not a proper one anyway. Although I did have a two-month affair the summer I was 15, it was a rather uneventful three-way with Martha Stewart and Anna Olson. Every day I would roll out of bed just before noon, pull my favourite slouch-chair in front of the TV and watch Martha Stewart Living, followed by Sugar with Anna Olson, followed by From Martha’s Kitchen. Every. Single. Day. (In case anyone’s wondering: no, I did not learn anything from these shows except that I can, in fact, drool without noticing for quite some time.)

Dear Diary: I’m going back to the little cliff that overlooks the bluffs with Jimmy again today and I’m freaking out because mom didn’t wash my black overalls (the pair she thinks is “too small”—yeah RIGHT). I should probably wear pants anyway, ’cause last time my legs got all scratched up from the thistles and mom made a face when she saw and asked what I was doing and I don’t think she believes that I was with Lisa.

8. The Bachannal (better known as Caribana)
Another never-was. To this day I have never attended Caribana, the great Caribbean parade held every summer in Toronto. When I was too small for “the jump up,” I got to participate in Kiddies’ Carnival, a kind of mini pops version of the real thing held the day before. I had a blast walking the pavement in my costume, so it would make sense that once I outgrew the kids’ parade I’d move on to the real thing, right? Not so. Historically the event has, at times, included violent incident. To be fair, violence isn’t a consistent feature of the parade from year to year, but as far as my mom was concerned that detail was irrelevant. (Not long after the 2012 shooting at the Toronto Eaton’s Centre, she looked at me with genuine horror when I headed to the same mall. You get the idea.) Under no circumstance was I permitted to attend Caribana, which still makes me feel like a counterfeit Caribbean-Canadian. Now that I am technically an adult I could right that wrong but, to be honest, it just wouldn’t be the same. I won’t ever be able to “jump an’ wave” with the abandon I would’ve indulged in my teens.

Dear Diary: I went down to Caribana with Anna and Gina and them today, and I have the most intense tan lines ever. I felt so lame for the first half ’cause I can’t wine my waist to save my life (unlike Gina, holy shit) but then we met some guys and one of them danced behind me and held me so you couldn’t really tell. I bought a Trinidad & Tobago flag to wave even though we had towels with us—when “LEMME SEE YA FLAG INNA DI AIR” plays it sucks to have nothing but a towel. The guy charged me TEN DOLLARS though! Worst.

9. The Pool Hop
To my knowledge, pool hopping was something that happened on TV, in teen movies, and in the states. Only in my twenties did I discover that this was a local phenomenon as well, that kids who lived in my city, who went to my high school, climbed fences for illicit swims. It was a revelation. How could I have been so unaware? Was it my indoorsy disposition? My chronic fear of the police? Most likely it was a combination of the two along with the fact that I just wasn’t that cool.

Dear Diary: Tonight we hopped the fence to go swimming at Christie Pitts but then security showed up and I panicked so hard that I forgot my towel on the other side! Ugh my pants are soaking and I’m sniffling from being all wet the whole the trek home.

10. The Club Night
My first nightclub experience was far from unique, especially for one in Toronto: an all-ages event held at the soon-to-disappear Guverment night club down by the lakeshore. After applying liners, glosses, and glitter, a gang of us spilled out of Anna’s house and down to the massive building encircled by kids as young as twelve, and men as old as forty. We were fifteen.

Dear Diary: We went to Guverment last night—it was so packed that you couldn’t really dance. I didn’t see any cute guys but I also didn’t really look around because every time I accidentally made eye contact with some guy they would try to grind on me. GROSS. I mostly just stuck by Kelly and kept my hands on her shoulders. We wanted to check out the techno room upstairs and made a chain to get through the crowd. Sheila was at the end and some guy grabbed her wrist and we all had to yank her free. He was holding her pretty tight, her wrist was sore after. We walked home with a group of guys we met in the parking lot and one of them told me his name was Santana (but his friend said that was a lie, whatever). He kept asking me out and I was too scared to say no so I just kept laughing and I think he thought I was crazy. I don’t think I like clubbing.



Chalsley Taylor is on the very brink of graduating from the Creative Writing program at Concordia University. Her short fiction was recently published in The Void. She hopes to finally attend Caribana this summer. Chalsley is the managing editor of carte blanche.