good bar 14th st to 30th st, par avenue - ish
i agree flatiron lounge is nice.
there's also sugarcane, attached to sushi samba on park ave btwn 19th and 20th. good cuban/brazilian/latin drinks
has a nice bar and great sangria. 19th btwn bway and park ave s
good cocktails at the bar in this restaurant on madison ave at 29th
20th btwn bway and park ave s
although it's a restaurant, they have a nice, large lounge area
and of course bar jamon on 17th at irving but i suppose that's not very fair to your friend! :)
I'd highly recommend Flatiron Lounge. They do high-end (quality) drinks a la Milk and Honey and that scene, it is usually not horribly crowded, and the crowd leans away from drunk kids and more toward people on dates or grabbing drinks before dinner. I've never had a bad experience. Even on weekends, the place is manageable.