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Think of Ryan Gosling and Emma Stone tripping the light fantastic by a Los Angeles cityscape at dawn in La La Land. Or Woody Allen and Diane Keaton huddled on a park bench under the Queensboro Bridge in Manhattan. Or Hugh Grant mooning over Rachel Weisz in the dirty, pretty streets of London in About a Boy.

Now add Winnipeg to that roster of romantic cities. Yes, Winnipeg... in director Tyson Caron’s romantic comedy Lovesick.

The opening title shot from Lovesick shows Winnipeg's Exchange District in all its romantic glory.</p>

The opening title shot from Lovesick shows Winnipeg's Exchange District in all its romantic glory.

It seems a stretch to be sure. We’ve become accustomed to seeing our city in a more unflattering light, whenever Winnipeg played itself in TV and movies. Remember the frozen urban wastelands of the HBO series Less Than Kind or the delirious, Kafkaesque cityscapes of Guy Maddin’s My Winnipeg.

But as soon as the opening title comes up in Lovesick, showing dejected hero Dash (Jacob Tierney) walking the lonely cobblestone streets of the Exchange District at night, we are confronted with a Winnipeg of soulful beauty and endless romantic possibilities, from funky art galleries to the Assiniboine Park train ride.

In the film, Dash struggles with his attachment to his longtime girlfriend Lauren (Jessica Paré), newly engaged to his romantic rival Mark (Jay Baruchel). Dash is so handicapped by his fixation, he doesn’t recognize the possibilities when he meets Nora (Ali Tataryn), a vivacious woman with her own baggage, including her mother’s penchant for binge drinking.

Tyson Caron</p>

Tyson Caron

Caron, 39, originally hails from Kenora, but has made his home in Winnipeg for the past two decades since attending and graduating from the Asper School of Business. Given that the plot of the film is taken from his own romantic experiences, the city of Winnipeg became inextricably linked with the action onscreen.

"I love Winnipeg," Caron says over a bottled water at the Free Press News Café, just a few steps away from the film’s opening title shot.

"Maybe there’s times when I see Winnipeg through rose-coloured glasses," he says. "But there’s enough negativity about this city that we don’t see there’s also so much beauty, and you don’t have to go far to look for it. There’s lots of great architecture, there’s lots of amazing art, some amazing communities."

The sheer beauty of the city, as captured by director of photography Jonathon Cliff (Brian De Palma’s Redacted) proves to be an ironic counterpoint to Dash’s moping depression.

"You have this character who’s having a real hard time, but the city around him is still beautiful, and I wanted to contrast those two," he says. "I wanted to show Winnipeg in the best light I could.

"I’ve been all across North America and there’s so much beauty here and so much life," Caron says. There’s some hard things about Winnipeg and some challenging things, but we didn’t focus on that."

Simultaneous to settling in Winnipeg, Caron fell in love with cinema, and determined to make a career for himself back in 2002, when he won a $25,000 grant to make a short film. He subsequently has worked in multiple capacities, serving the crews of projects as diverse as production manager on the series Tipi Tales (for the production company Eagle Vision, the producers of Lovesick), an associate producer on the kinky comedy Walk All Over Me and third assistant director on Guy Maddin’s Keyhole.

"Guy’s style may be completely different, but to work with someone like Guy, to see how he communicates with actors, how he communicates with the crew, you learn a bit about how to work on your own set."

Supplied</p><p>The neurotic Dash (Jacob Tierney) gives the lovely and witty Nora (Ali Tataryn) a ride on the handlebars of his bicycle in Lovesick.</p>

Supplied

The neurotic Dash (Jacob Tierney) gives the lovely and witty Nora (Ali Tataryn) a ride on the handlebars of his bicycle in Lovesick.

After writing the script for Lovesick, Caron wasn’t sufficiently confident to claim directing rights himself. In fact, the film’s star Jacob Tierney had been asked to direct once the script started taking shape. The Montreal-based Tierney, who directed the Baruchel comedy The Trotsky, agreed to take the lead role, but insisted Caron should direct. In his capacity as executive producer, he helped the film enlist fellow Montrealers Paré and his childhood friend Baruchel into the cast.

"Jacob is so connected in the industry and he’s built all these relationships," Caron says.

Even if the film started out as Caron’s own story of post-breakup heartbreak, he says it "evolved" to the point where "it became something of its own.

"When I see it now, none of this actually happened to me... maybe a couple of little things — slivers," he says.

It may be that Caron feels the distance because he got his own happy ending. He’s the proud father of a six-week-old boy with partner Winnipeg architect Mamie Griffith.

"He’s the greatest thing I’ve ever seen in my life. I just can’t stop looking at him," Caron says. "When you feel that love for your child, it’s like nothing else."

randall.king@freepress.mb.ca

Twitter: @FreepKing

Randall King

Randall King
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In a way, Randall King was born into the entertainment beat.

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