Small prairie towns are no place for a fervid skateboarder. “The roads are crappy and there are no hills,” says ColeNowicki of his hometown Lac la Biche, Alberta.

The 24-year old came to Vancouver four years ago in pursuit of greener pastures (AKA smoother concrete) and settled in the Commercial Drive neighbourhood—in great proximity to the city’s skateparks, but also in prime people-watching territory.

In September 2013, Cole started documenting his “run-ins, pass-bys and overhears” with Vancouverites—capturing their quips and quirks, using them as a platform for reminiscence or introspection. He posts 2 or 3 original sketches each week on his Tumblr, “Portraits of Brief Encounters.” It’s what might happen if you placed Humans of New York in Vancouver, and replaced its photos and overt sincerity with a sharpie and a healthy dose of irony. Cole’s keen observations and wry sense of humour make Portraits a resonant visceral experience. The result is poetry, both written and visual.

“I’ve always liked making things—drawing painting, making figurines out of twist ties. And I like storytelling so this combination of art and text seemed like a natural progression,” he explains.

Inspired by fellow skateboarder and contemporary artist Ed Templeton, Cole loves the connection between skateboarding and art: “Skateboarding is my passion—the longest relationship I’ve ever been in—but it’s also where I gather creative inspiration.” He combines the two on his skate/art site: sundaydrivedigest.com

Cole will be creating an original sketch for Sad Mag once a week, but in between you can follow his Brief Encounters project on Tumblr and Instagram.