Before you groan at another Union Square request, hear me out.
Seems I always have friends come into town who I end up meeting near Union Square. Always trying to figure out a nice, non-stuffy location to take them for a drink that is nearby. Above all it should be a low-maintenance, non-imposing place.
That's why I have been avoiding the hotels ... I know that they might provide what I need, but am daunted by the stuffy hotel setting (maybe I'm wrong? if so, tell me).
I always do fine if I have time to take them to other locations of the city, but get stuck right around Union Square.
Usually end up going to First Crush (Cyril Magnin @ Ellis) ... but after my last trip there, I would prefer not to go back. I don't like their food or the vibe that's there. They provide wine flights, which are fine, but nothing about it reflects the things that I love about San Francisco: individual, comfortable, not snobby.
Requirements: Wines by the glass, full bar, good snacky appetizers. Quiet enough to have a conversation. Could be a restaurant if they don't mind you just going in for a drink and a snack. Preferably open in the afternoon and late at night.