5 Trendy Chicago First Date Restaurants

Whether it's a casual meet-up, a heart-fluttering full-tilt swoon, or a lucky, lucky chance to reveal your true intentions, why wing that first date? We've put together a tidy little list of five can't-miss Chicago watering holes and cozy restaurants to breeze through the ritual.
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First dates, and first impressions on dates, can fizzle or ignite interest in 20 minutes or less, according to a Texas University study. And a 2009 speed-dating survey from the University of Indiana showed decisions about pursuing a love-thing (or sample and move on), are made within seconds. Who pays is still a sore spot: In an NBCnews.com study of more than 17,000 singles, 44 percent of men said they would dump a woman if she didn’t offer to chip in on dates, and 44 percent of women were annoyed(!) when asked to pay. Here’s a novel solution: Settle that up front. 

Those stats shocked us. But we kept wondering where these people coupled up. Now, this is unscientific, but doesn’t it figure that the way to gain some evolutionary advantage on the first meeting-of-the-minds is a stellar venue? Natch. And Chicago has them in spades.

Confession: These selections are whittled from dozens of potentials or this would have ballooned into a Zagat guide; if your favorite is absent, it’s not personal. From the Fulton River District to Lincoln Park, we tried to accommodate a menu of date vibes: hip, young, fun and a wee bit loud is represented; quiet rooms for handholding and gazing; sophisticated cuisine for the experimental; vegetarians, we thought of you, too (you’ll find something delectable and meatless).

One caveat: These five aren’t bulletproof; that is, we can’t guarantee that great food and superb ambiance can overcome date bombs like flirting with the cutie at another table, licking your plate, self-absorbed chatter about your exes, or texting-while-wooing. Barring that (please), perhaps one of these spots could nudge you into the Second Date Finals and not exiled (yet) to the “friend” zone.

Sepia in Fulton River District

Sepia is built in an 1890 print shop and it's filled with Old Chicago memorabilia and photos. This Michelin Star outfit is Chef Andrew Zimmerman's invention and it's an instant classic. Choose this for a big date night dining experience of wine, conversation and an American cuisine menu with striking entrees. Must-tries include the roasted poussini with Roman gnocchi and wilted chicories. Is the date out of the danger zone? Then order the flourless chocolate cake with tequila gelee for dessert. Located at 123 N. Jefferson St.

Sunda in River North

Named after an Asian trade route, it's not unusual for Lady Gaga or Mark Wahlberg or director Michael Bay to drop in Sunda, one of the most popular spots on the scene. Pick this for an adventurous date and the fusion of Southeast and East Asian plates from the talented and funny Chef Jeff DeGuzeman. Vegetarians are covered with this chic, inventive menu (Veggie Q Sushi Rolls). Here's an idea (and you'll score major originality points): Plan a date for the Monday Maki Sake class ($25 a head) and learn to make sushi and sip on TyKu sake. Thinking about it, aren't you? Located at 110 W. Illinois.

Hub 51 in River North

Party central: The menu is a mad sprout of sushi, burgers and tacos. Try the filet mignon steak tacos and charred salmon, and imbibe your pick of sake, wine or a wide beer selection. We'd choose this for a casual "we're just hanging for a minute" date. But if the date has morphed into crash-and-burn, do not despair! This place has a built-in escape hatch during the weekends where you can flee to Sub 51 for lounge action and DJs helping you dance off the date willies. (DJ Koncept spins every Saturday night.) See how that worked out? Hub 51, 51 W. Hubbard.

North Pond in Lincoln Park

You will be burned into your date's memory if you choose this romantic gem on a bluff with views of the gentle Lincoln Park pond. This is a restaurant steeped in the Arts and Crafts tradition, from the 1912 building to the fresh, local, seasonal produce from small farms that are a staple of Chef Bruce Sherman's kitchen. The pan-browned duck breast with charred peaches and compote just rules. This is a place for whispers, private toasts and the clever double entendre. Float right in. Located at 2610 N. Cannon Dr.

Rebar in Trump Tower

Grab neo-Japanese eats in a bar inside the tallest residential tower in this hemisphere. Rebar has the Lake Michigan views, the upscale heat and the prices ($11 bucks for a rancic hand roll, $22 for 8 pieces of shrimp Tempurah). This is the Trump, so we suggest you use this as the perfect launch pad for the evening. (Thinking to self: Yeah, this could work. To date: "Let's head over to ..."), or a pass/fail testing ground to keep your options for the remainder of the night open ("Would you look at the time!"). Nothing wrong with a little strategy deployed with skill. Located at 401 N. Wabash Ave. 

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