I can't imagine it would, at least not without some (a lot of) social lube. Even bars might prove hard, since a lot of people there will be the regulars and other fixed groups who probably aren't interested in making friends. If you could join the smokers for a fag that might work out, but that doesn't happen any more since you can't smoke outside public establishments (which is fair, but it does remove a potential social arena).

It's reasonably possible at events. Cars and Coffee works great, since everybody wants to talk about their car. I doubt it will work at the dentist, since nobody really wants to be there in the first place. Maybe if they're wearing a shirt or something you can compliment or ask about and then can use that as a springboard?

If you're the dictionary definition of an extrovert you can probably still make it work, but you'll really stand out, and you'll be rejected a lot.