I would have sworn we covered this topic recently, but I searched back to '01 and couldn't find it. We did talk a little about favorite servers/barkeeps, but not bars in general.
I love Harry's in Westport, and I go often. The problem, on a Friday or Saturday night in the summer, is that it is... you know, in Westport. With all the craziness that entails. Sometimes that's the scene you're in the mood for, sometimes it's not, and for this weekend, I want something a little calmer. A good friend of mine will be in town, and while people-watching is great entertainment, we'd also like to be able to hear ourselves talk.
So I'm looking for alternatives to Harry's, if we get there and the frat-party ambiance of Westport gets to be too much. It has to be somewhere south of the river and north of 75th - Brookside, Plaza, 39th st nabe, or downtown. Other things I'd like to have, in order of importance: great waitstaff (I think some people have suggested JJ's for this), good/varied beer on tap (a great Guiness would be nice, that's something not every bar has a handle on), good food served late.
When you want a comfortable, friendly place to sit, have a few, and talk for hours, where do you go?