The postcard-size photo, with my father on the left, was taken on the street in Sydney, Australia, early in 1941. The reverse side indicates it was taken for the Leicagraph Co, 5 Strand Arcade, Sydney.
The street snapshot was a thing in Sydney, competing companies took photos of people walking in the street, then handed them a card indicating where they could go to view and buy a copy. Read all about it in a post from the Museum of Sydney.
I recall similar casual photographers at seaside resorts in the UK, decades before smartphones and the ubiquitous selfie. You may have encountered the same sort of thing — photographers poised to take photos of passengers joining a cruise. Do they still do that?
Was this a thing in Canada? The Ottawa City Archives guide to photographic collections makes no mention of street photographers. Google “street photography Ottawa” and you’ll find several people taking artistic photos of street scenes.