Dear Toronto,

Okay, I’ll come out and say it—I’ve never been your biggest fan. Sometimes you act like you’re the only city in Canada. And, worse, sometimes the rest of the world agrees. While I have family and friends who live in Toronto, I’ve always found you a little disjointed, and, well, cold. With your iconic CN Tower, SkyDome, and Lakefront District, it’s hard to see you as anything but a poser. If you were a character in a movie, you’d be the uptight yuppie striver. But one of the most pleasant surprises in Pretend We’re Kissing was getting to see a different side of you.

We’ve all watched films that are supposedly set in New York, L.A., or Chicago, only to have a Shoppers Drug Mart or Maple Leafs ad in the background give you away. There’s been a recent trend of Canadian filmmakers eager to show you off; Sarah Polley’s Take This Waltz, Atom Egoyan’s Chloe, and Michael Dowse’s The F-Word have been content to just let you be you. In his first scripted feature, Pretend We’re Kissing, writer/director Matt Sadowski seems particularly besotted with you, and he’s not shy about letting it show.

Billed as a “non-rom-com,” Pretend We’re Kissing is about what happens in the days that follow a couple’s first perfect night together. Benny is an introverted artist plagued with nagging self-doubt. When he connects with Jordan at a concert and is too shy to approach her, he figures he’s lost his one chance. But, of course, they run into each other again, and both of them see it as a sign that they were meant to meet. However, after their first romantic encounter, they learn that you can’t force a “happily ever after.”

Blame it on the influence of actual rom-coms, but many of us secretly long to be swept off our feet. Unfortunately, the reality of falling for someone at first sight is never as perfect as the movies make it seem. The dialogue isn’t effortlessly witty, the first kiss isn’t always well-timed, and the sex isn’t always mind-blowing. Sadowski has fun with these genre conventions and lets the scenes between Benny and Jordan play out in a natural – and often uncomfortable – way. It helps that actors Dov Tiefenbach and Tommie-Amber Pirie look like regular, attractive twenty-somethings and not perfectly-coiffed Hollywood glamazons. They fumble, they overreact, they try too hard—just like real people. It would have been easy to play these characters for laughs, but it takes genuine talent to underact as naturally as they do.

Complicating Benny’s life is Autumn, a twist on the Manic Pixie Dream Girl. She’s a childhood friend who’s been squatting in Benny’s living room for the past year, inviting strangers over for random hookups and using all his toilet paper. A self-diagnosed agoraphobic and faux spiritualist, Autumn is kind of a nightmare, but she does give Benny the back-handed advice (“don’t be a Benny”) that he uses to nab Jordan. Zoe Kravitz’ Autumn is adorably kooky and believably annoying. It’s no wonder Benny spends all his time outside the apartment and on your many bustling streets.

And it’s there, on your streets and in your neighbourhoods, that Pretend We’re Kissing overcomes it’s “non-rom’-com” conceit. As a band flyer designer and posterer, Benny’s vocation finds him in various locations around the city. I was charmed by your countless colourful surprises – the Dutch Dreams treat shop, the Cameron House tavern, a retro bus shelter, a brick building with “You’ve Changed” written scrawled in stories-high block letters – and the manner in which they were presented. Sadowski frames his shots thoughtfully and lingers on them. This approach overcomes both the usual indie style (shaky hand-held) and the clichéd rom-com conventions (soft-focus close ups). This works especially well when highlighting the characters’ most awkward and the most vulnerable moments. But at times this effect can be more plodding than pleasing.

Though Pretend We’re Kissing does eventually cross the line into rom-com territory (the cutesy ending is a little pat) your environment feels surprisingly fresh. You can be every bit as charming and exotic as Paris or New York. Even your CN Tower reinvents itself as romantic: a scene in which a snuggling Benny and Jordan make their way back from Toronto Island Park is reminiscent of the Brooklyn Bridge scene in Manhattan.

Like any new relationship, I suppose I was guilty of projecting my expectations onto you. I begrudgingly admit, you grew on me. It is possible to fall in love in Toronto. And with Toronto. But if this film taught me anything it’s that maybe we should wait and see what tomorrow brings.

Hey, if we can make it here, we can make it anywhere, eh?

P.S. Leafs still suck :)