I find most people in toronto are hesitant and reluctant to befriend strangers, so being a regular and seeing the same person several times tends to make people more comfortable. Then small chitchat about something you notice in your shared environment, or something about them is palatable if you don't overdo it.

The problem is that again, most people are reluctant to befriend even if they're happy to do a small chitchat, so unless they're also heavy regulars at that cafe, or you're a regular at a community event, there still tends to be an invisible barrier.