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Where to Have the Dinner Date of Your Dreams (or Nightmares)

BY: Aimee Algas Alker | Feb 11, 2014

Certain restaurants seem designed for getting to know someone special. Dipping sweets into molten chocolate at a fondue spot almost guarantees your fingers will touch, and dinner at a restaurant lined with mirrors ensures that you won’t have to get up from the table to see if you have food stuck between your teeth.


But sometimes it’s not so obvious.

So let us, the Guide Staff, share our tales of romantic restaurant triumphs and shortfalls.Here are our recommendations for where to bring a date—and where you might be better off inviting someone else.


Henri (The Loop | 18 S. Michigan Ave.)

Why to bring a date: My boyfriend surprised me with a reservation for our five-year anniversary, and as soon as we sat down, the staff wished us a happy anniversary, presented us with personalized menus memorializing the occasion, and handed us a complimentary champagne toast. The food was spectacular, and the personalized service was the cherry on top—I still have those menus. – Sarah Gorr

Hopleaf (Uptown | 5148 N. Clark St.)

Why to bring a date: Hopleaf's selection of countless craft brews, both on tap and by the bottle, allows me to properly judge how much of a beer snob my date is. If nothing else, I know I'll be leaving buzzed on delicious beers. – Shannon Jewitt

Quesadilla La Reyna del Sur (Bucktown | 2235 N. Western Ave.)

Why to bring a date: The hours are completely unpredictable, and the staff celebrates holidays I've never heard of by taping an apologetic sign on the door for weeks at a time. That means, on every visit you either experience the exciting team-building exercise of finding a new restaurant with no notice or an amazing vegan taqueria feast. – Cody Braun

Boiler Room (Logan Square | 2210 N. California Ave.)

Why to bring a date: Two days after I met Tom, I found myself walking toward him at a then-newly-opened pizza joint called Boiler Room. I was nervous, but it was easy to bond over undeniably great cornmeal-dusted pizza and Jameson ice cream. We’re engaged now, and still share ice-cream cones during date-nights at Boiler Room. – Halley Lawrence

Pitchfork (Albany Park | 2922 W. Irving Park Rd.)

Why to bring a date: We used to live just around the corner, and Pitchfork became our go-to spot for a quick bite to eat. Those ribs are delicious, and good for seeing whether your date can handle a faceful of barbecue sauce. But there are neater options if you happen to visit during the honeymoon phase of your coupledom. And if things take a turn for the uncomfortable, a vast menu of whiskeys is scrawled on the chalkboard behind the bar, just waiting for your nod and point. – Aimee Algas Alker

Sabatino’s (Old Irving Park | 4441 W. Irving Park Rd.)

Why to bring a date: This is an Italian restaurant of the old guard. Dim lights, cushioned seats, generous pours of wine, all make for an ultra-romantic night. Snag one of the curtained booths and get a little private time, or swoon to the sounds of the violinist who traverses the room on some nights. – Aimee Algas Alker


Cafe Iberico (River North | 737 N. La Salle Dr.)

Why not to bring a date: I adore Cafe Iberico, and I'm especially fond of the skewers and the potato salad. But this dude would only talk about himself, which made conversation—and therefore sharing every damn plate with him—super awkward. – Aimee Algas Alker

Who to bring instead: Your best friend with whom you’re comfortable sharing everything, even potato salad.

Mitad del Mundo (Logan Square | 2833 W. Armitage Ave.)

Why not to bring a date: We were there early, and the restaurant was completely empty. During each long, awkward pause in our conversation, you could hear papel picado banners rustling overhead, like some obscure indoor species of cricket. – Nathalie Lagerfeld

Who to bring instead: Anyone else, as long as it’s karaoke night, which we hear is hoppin’.

King Crab Chicago (Lincoln Park | 1816 N. Halsted St.)

Why not to bring a date: The place is jaunty and loud, just like a pirate, not the best place to take someone you're trying to impress or get to know. – Aimee Algas Alker

Who to bring instead: Ideally, an actual pirate, but a boisterous group of friends will also do.

Kuma’s Corner (Avondale | 2900 W. Belmont Ave.)

Why not to bring a date: It's dark, although that's probably good because you'll more than likely end up covered with large quantities of whatever is topping your ridiculous burger. [The real problem is the music.] They dig way deeper than the sort-of-ironic Iron Maiden cuts you hear at faux metal bars and into really bleak Scandinavian stuff. Your date will not be louder than it. – Cody Braun

Who to bring instead: A platonic friend with a megaphone.

Photo by Andrew Nawrocki, Groupon

Guide Staff Writer
BY: Aimee Algas Alker
Guide Staff Writer