A broad suggestion: Make it look like a biz dinner.

Hi there.

In my experience, one runs the risk of bumping into friends / colleagues / wives friends / etc REGARDLESS of where you go. Regardless of whether you are at an intimate little bistro or a more bustling establishment.

So why don't you and your lady friend "dress the part" of people on a biz lunch or dinner? I will wear a pencil skirt, blouse, tasteful heels, etc, slap a "wedding ring" on my hand, and (sometimes) even take my laptop case with me. And then my friend and I can still flirt and get romantic during our meal ... But we keep the petting to discreet touching under the table and dirty banter. We refrain from making out at the table or doing other things colleagues wouldn't do. lol

Oh yes - and have a cover story which you both quickly memorize ... lest you run into someone and need to quickly explain it away.

These may seem like great lengths, but they really have (in my presence) saved the hides of a few people I know.

Best of luck to you!

Ooohhh, nice topic! I love, love, live...

Geja's Cafe!  It has live soft music and a soft candlelit ambiance and if you reserve early enough you can procure a sweet little private table in a one of their few nooks.  Also, after the kitchen closes, they put away the tables and open up a dance floor for flamenco dancing

I also love Sabatinos, cafe Absinthe and Emilio's Tapas.  Man, now I'm hungry!  Anyone want to take me out to dinner?

XXX-Giselle

I guess it would be considered West Loop area, just north of Greektown. I think it fits the bill. Great food and it is intimate.

If it is still there, it would be perfect.  It's on Mannheim in Rosemont.   Very dark and romantic.  If you saw someone you knew there it was no problem because they were with their "someone else" also!

I haven't been there in years.  You could the Google thing to see if it's still in business.

Untitled located in downtown chicago.  It is an old speakeasy - style restaurant with a main dining room and a few offshoot dining rooms.  I was in one of the offshoot rooms which featured private booths with cloth that you could pull across and completely seclude your party from the rest of restaurant,Once in your private booth you can order drinks, meals, etc at will, enjoy the music from the main band, and still have a secluded and special atmosphere for your friend.  After having a great time in your private booth you can expand into the restaurant's bars where there is a great dance floor, another large bar, and live music.

I would really recommend it, it is a fun time for a group of friends to start drinking and eating in the private quarters, then move to the dancing later in the night.

http://untitledchicago.com/

It's under a collapsed roof due to a few tons of snow! Oops!

Xoxo
VC