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Where to meet a group for drinks?

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We'll be in New York (visiting from DC) in a few weeks and would like to meet up with a group of friends for a post-dinner drink around 11 pm on a Saturday. Ideally we don't want to pay a cover or for an overpriced table with bottle service. Just somewhere laid back, nice (ideally not a dive), and not packed to the gills with people where a decent-sized group of us (15-20?) can gather. A wine bar or lounge would be great.
Our friends primarily live in Union Square, Chelsea, and Gramercy, but we can certainly pick somewhere outside of those areas.

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  1. I think that Flatiron Lounge on 19th between 5th and 6th would work - great atmosphere and terrific cocktails. It can get somewhat crowded but it should still be okay, though you probably won't be able to get many seats (that that may or may not be important).

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    1. What about: Cibar, Candela

      1. Flatiron Lounge is a good choice. Another laid-back and nice place is CiBar on Irving. If you want a slightly larger spot you could check out Slate. Downstairs, there are pool tables, and upstars are large booths for seating. I've been there a few times and had a booth without having to pay for any kind of bottle service... Good luck!