This is outside of your parameters, but I'm a huge fan of
Dram, right over the Williamsburg Bridge in Brooklyn. A cheap, quick cab ride from lower Manhattan.
Jeremy makes outstanding cocktails and is just an all-around friendly guy, who made great drink suggestions and also suggestions for other bars and restaurants to check out. On our last visit to NYC, in November, it was the only place we visited multiple times. It's a small bar with serious cocktails, a relaxed atmosphere, and ample seating. Even on a weekend night, it was full, but not terribly crowded - - and no lines.
If you want to impress your friend with serious cocktails, I think this is a good option. However, if you're looking for a scene, this ain't your place. For a Chicago comparison, I'd say the vibe is similar to Whistler, with an interior akin to Avec.
There are also plenty of good restaurants nearby, if that's of interest.
Ronna