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Suggestions of where to grab a first date drink...

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I'd love some suggestions of where to grab a drink for a first date on Friday. No time has been set but I'm imagining 8 pm.

He's new to the area and I'm relatively new as well (6 months) so I need a little bit of help. We're both foodies with a penchant for things that are a little more gourmet or upscale, but not necessarily creme de la creme. (Not that this intimidates me but going too fancy on the first date to me seems out of place.) We're also both in our late 20's/early 30's if that makes a difference.

Ideally I'd love a place that:

A) Has something unique going for it - a cool atmosphere or expertise. Something with more of a touch of special than your average pub. I am definitely drawn to great wine bars or places that have prohibition themed cocktails.

B) Isn't going to be TOO loud or crowded. A bit of a scene is okay but I'd like to be able to grab a table and hear him or it defeats the purpose.

C) Isn't just about beer. I don't personally drink it (though a good artisan hard cider or cocktail is a-okay) so if something is exclusively a brew pub I'm going to feel a bit odd.

Any suggestions. He's in Old Town & I'm in Lincoln Park but I'm completely open to anything that is reasonably cabable if it's good. (I'd offer up suggestions of what I normally like but given they are places in Boston they might be meaningless. However, in the off change anyone has I'd love the Chicago version of a place like Drink or OM.)

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  1. Go to Sable Kitchen or Balsam at the Elysian Hotel. Sable has a young, yet still upscale and gourmet, vibe and if you guys hit it off the food is yummy. Balsam is a bit more private, the cocktails are to die for! Oooh, or Violet Hour in Wicker Park- super sexy and all hand crafted cocktails. Good luck!

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    Violet Hour
    1247 N Damen Ave, Chicago, IL 60622

    1. Carag's suggestions are spot on. The Violet Hour will be tough at 8 p.m. on a Friday night. You'll easily have a wait, possibly up to an hour which is a downer on a first date.

      Two other options: Gilt Bar right near Merchandise Mart. A more funky, off the beaten path option is California Clipper in Humboldt Park. Great cocktails, no tvs.

      Have fun!

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      Violet Hour
      1247 N Damen Ave, Chicago, IL 60622

      1. For a first date I would have to say the Trump Tower outdoor rooftop bar... Well, it's not actually rooftop, but rather the 16th floor. It does have a little scene but my boyfriend and I went once soon after relocating to Chicago and we were in awe. With the weather so nice, it's a great place to sit outside and admire the lights, the architecture, etc etc. It's romantic/sexy without being fussy.

        They have a full bar so of course they have your typical martinis and whatnot but also have some delicious in-house recipes.
        If you do go, just note that the two bars adjacent to one another (one inside, and the deck) are different bars and don't allow you to take the drinks to the different areas (kinda lame).

        1. I'm from Boston, where did you used to go? My suggestions would be Tiny Lounge in Lincoln Square (which has a bunch of fun bars in the area for further drinking). Violet Hour is great, but hard to get into sometimes. I love Delilah's, which is a "rock" style bar (has great drinks and is unique, but might be loud). There's also Zed 451, which has a fun rooftop (which I've found to not be loud compared to many rooftops, like the Wit), and it's across from Clark St Ale House (I know, but it's a good beer bar).

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          Tiny Lounge
          4352 N Leavitt St, Chicago, IL 60618

          Zed 451
          3000 Finley Rd, Downers Grove, IL 60515

          Violet Hour
          1247 N Damen Ave, Chicago, IL 60622

          1. If you don't mind going down town, try the bar at Sepia (near Randolph and Jefferson). Like Violet Hour they specialize in classic cocktails. They have a great menu of drinks, but the bartender is quite willing to make you something off-menu if you give him your likes and dislikes. It is more a restaurant than bar, but it still has a nice bar area. It definitely meets your desire for a cool space - it's an old printing building.

            If a wine bar is what you are looking for, I think Bin Wine Cafe in Wicker (on Milwaukee) park would be quite nice for a first date - and there of plenty of other dinner and drink options right around for later in the evening. They have a nice selection and the space is quite nice and welcoming. They also have nice cheeses for snacking - not sure if that's a good first date idea though!

            I think the previous suggestion of the Gilt bar is also good. The Sable bar can sometimes be dead, which could make a first date a little more awkward I would think.

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            Bin Wine Cafe
            1559 N Milwaukee Ave, Chicago, IL 60622

            Violet Hour
            1247 N Damen Ave, Chicago, IL 60622