The guy who ran WordCamp Toronto 2008 was sort of doing the meetups in Toronto. I signed up on that meeting site (it gave you a chance to rsvp and get updates), I had bad luck as I had work related issues/events dumped into me last minute for a few months. Eventually he gave up/quit/left.
I tried to take over the "group" but the website asked to pay to manage the group.

Anyways, no one too over the meetup (i think that's the name of the website), it went the way of the dodo bird. I would love to start a WordPress meet up - monthly maybe?
I have no idea how to start it, I could talk to the people running WordCamp Toronto 2009 which are Toronto's open source culture group. I just don't know how to go about it.

By the way, why are you not speaking at WordCamp Toronto 2009? This fact alone is making me cry in my bed night after night. Man I need a new pillow cover.