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Sexy atmosphere w/outdoor seating and killer wine list

Meeting up with an old friend/ex-boyfriend after six years and want a place with style and atmosphere that serves decent food and great wine. I don't want it to be too romantic... I am aiming for flirty/cheeky, so higher noise and energy levels are okay. If I can't find one place that offers all that, I'm happy to do drinks and wine in one place, to be followed by dinner somewhere else. Any neighborhood works, but I want to keep it in Manhattan. He works in the restaurant industry, and we may soon become colleagues. I am new to the city and have been given the task of choosing meeting place and would love to pleasantly surprise him with my choice. Help me all you fantastic chowhounds! A few places I've been tossing around so far...

Nero (drinks, maybe food)
Barolo (for the patio and vino)
Cafe Habana
Lovely Day (casual and tasty)
Bar Pitti
5 Ninth
Kittichai
Stanton Social (cocktails)
Death & Co. (after dinner)

Random, but haven't had much time to research my task. Thanks for any and all suggestions...I can't wait!

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    1. I like cafe habana and lovely day but theres nothing sexy about the atmosphere. I think you should save those for a casual night.

      Add Pegu Club and Angel share to the drink list.

      3 Replies
          1. re: DarthEater

            thats easy. i trulli. great outdoor garden and massive wine list with excellent food.

      1. Otto. Fun, stylish, loud - decent fun food (meat plates, cheese plates, various other noshes), extensive wine selection.

        1 Reply
        1. re: BaconBits

          OK - so I re-read the title of the post. You want outdoor seating. Go for Malatesta. Great location - you get a breeze off the water - outdoor seating - REAL tasty noshes! Enjoy!

        2. not outdoors (though much of the list so far is not) but public is sexy, has a large wine list, bustling enough to be flirty but not romantic and the has essentially an open wall with couple with an airy space may be close to an outdoors vibe.

          wined up (also indoors -- skylight / airy) has a great winelist and a decent variety of food / small plates.

          la bottega at the maritime hotel has a very large outdoor space... casual but tasty fare... actually not too sure on wine list, but as far as sexy outdoor spaces go, it fits the bill.

          1. I dig Stanton Social, and fun atmosphere. Sharing of plates, too. Not outdoors, though.