Ed & Mary's, over near Hamilton Park. It's a dive with a big beer menu, but unlike a lot of dives (I'm thinking of Lucky 7 and the like) they also have wine, cocktails, and a full bar, so if you don't know what your date likes it's a good option. They also have great, simple food if you get peckish. I almost hesitate to call it a dive because it's very clean and comfortable, but "dive" is pretty clearly the ambience they're aiming for.

Staff is awesome, and highly likely to make up for any gaps in conversation. The vibe is something like casually intelligent dirtbag leftist. I've seen a bartender cuss out an athlete on TV for sucking shit at the sports game that was on, then pivot and air his concerns about Universal Basic Income being a one-size-fits-all solution when it comes to minors, dependents, the mentally ill, and victims of domestic abuse.

If you're looking for something closer to the pedestrian boulevard and/or less casual, I'd say Hudson Hound. Not cheap, but if you're just getting drinks it's doable. Cocktails are unique and beautiful, the old wood and furnishings provide a real nice atmosphere, and again, great staff.