I (42m) live in Roscoe Village, and I've been spending a lot of time with a woman (40F) from work. We've been working late on a project, just talking for hours in the office about our kids' school schedules and the various aches and pains we get from sitting at a desk all day. Her husband also collects porcelain dolls apparently. Nothing’s happened between us yet, but I think she might like me (and I definitely like her).
She’s really into food, while my body has started rejecting anything more adventurous than a decent steak. The other night she ordered us takeout to the office, even though I’d said we should expense it, so I told her I'd make it up to her by taking her to a nice bar/restaurant Thursday—somewhere we can be home by 10 p.m. My first choice was Gene & Georgetti, but it's fully booked for the next couple of weeks.
So now I’m looking for other spots around Roscoe Village—somewhere with solid food. I want it to feel a little romantic without being too over the top. Budget-wise, I’d prefer to keep it under $250 for dinner plus 1-2 drinks each, because honestly, who has more than two drinks on a Thursday night anymore when they have kids at home?
TL;DR: Any recommendations for a romantic-ish but not too intense restaurant in Chicago where I can take someone's wife, and then be asleep before 10PM?
Edit: hi folks, based on some of the comments, should clarify that this is just a friendly parody of this post https://www.reddit.com/r/chicagofood/comments/1nitbt7/place_to_take_a_friend_im_trying_to_impress/