bars/pubs/lounges/places for drinks where 40somethings aren't out of place, where conversation is possible without straining your voice, and the music isn't turned up to nightclub levels between 10:30 pm and midnight....

Did something of a crawl a couple of months back with some friends in that demographic and tried a number of places on Ossington. Foxley, Reposado and Bellwoods Brewery all have decent patios and didn't seem to count the wrinkles. Decent apps (Foxley's whole menu is small dishes). From the point of view of decent places where you won't be treated as soylent green, The Saint, Salt, Boehmer, and Hawker Bar are decent places to sit down and nibble with a bevvy or two.