Chicago's Hottest Chefs On The Best (& Worst) First-Date Meals

Every first-date pro knows that you pick what you’re going to eat before you get to the restaurant. After all, what kind of impression does it make when you spend the first 15 minutes of the date with your nose buried in the menu? Exactly. Plus, if you're somewhere good, you want to make the most out of the occasion — while managing to sidestep the kind of dishes that could turn your evening into a meet-not-so-cute.

We polled some of Chicago’s top chefs and mixologists on the menu items you should order from their restaurants — plus, the items you should wait to order when you’re further down the relationship road. Then, you can have garlic breath and sauce-covered fingers together.
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Photo: Courtesy of Beatrix.
Executive Chef John Chiakulas, Beatrix
Offering up classic comfort foods with a healthful twist, this industrial yet homey restaurant boasts glass walls that open street-side to the patio for an awesome, summery, indoor-outdoor vibe.

Best Bet: The chili and chocolate-glazed salmon. "Served with corn tortillas, it is an interactive dish that is easy to share and will reveal a lot about your date," Chiakulas says. And, need we mention chocolate is a natural aphrodisiac?

Better To Avoid: "Even though I love the caramelized pork shank with cider reduction, it might look really big and like too much food for one person, which could be a little awkward or embarrassing on a first date," he says. (Seriously, it looks like something they’d eat on The Flintstones.) "Once you've fooled your date into liking you, definitely come back and try it! It really is worth it."
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Photo: Courtesy of Christian Seel.
Beverage Director Micah Melton, The Aviary
The Aviary’s swanky and expert-crafted cocktails are famous both city- and nationwide. The only way you can go wrong here is by overdoing it.

Best Bet: The Porthole, the bar’s custom-infusion device designed by Martin Kastner, is 1) gorgeous and 2) perfect for sharing cocktails, Melton says. Right now, The Porthole comes filled with a drink called "The Hollow," comprised of white whiskey, chrysanthemum, ginger, bee pollen, honeybush, and saffron. The device holds several servings, so, with every pour, the drink picks up more of the flowery, spicy notes.

Better To Avoid: "In The Rocks," a boulevardier filled with bourbon, sweet vermouth, and Campari is super fun — you smash it open with a slingshot — but it's too boozy for a first date, he says. And, probably for a second date, too.
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Photo: Courtesy of The Godfrey Hotel.
Executive Chef, Riley Huddleston, I|O Godfrey
Above The Godfrey Hotel, this indoor-outdoor rooftop lounge serves up small plates that are perfect for a casual date among foodies.

Best Bet: Start off with the charcoal-grilled octopus with fried potatoes and smoked-chili aioli. It's one of the most beautiful items on the menu and will show off your adventurous side. Next, ask for the chocolate bars. "They aren't listed, so you can impress your date by asking for this off-the-menu item," Huddleston says. They come in three variations: coconut jam with almonds, orange marmalade with pistachio, and peanut-butter mousse and jelly.

Better To Avoid: The delicious — but potent! — grilled pork belly. "This particular dish contains a lot of garlic; not exactly something you want to deal with the rest of the evening," he says.
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Photo: Courtesy of Troquet River North.
Beverage Manager Breanna DiMaggio, Troquet River North
A bar-and-restaurant in one, this Paris-inspired locale is perfect for a first date. Start with drinks and, if things go well, move on to dinner. Come on Wednesday evenings for live music.

Best Bet: This summer, DiMaggio recommends sipping on a watermelon mojito. A combination of rum, watermelon juice, mint simple syrup, fresh mint, and lime, it's clean, refreshing, and just flirty enough.

Better To Avoid: Red wine. "You never want red-stained teeth on a first date!"
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Photo: Courtesy of Anthony Tahlier.
Chef Ryan McCaskey, Acadia

This South Loop Michelin-starred restaurant is high-class, but its à la carte price points are perfect for a first date.

Best Bets: McCaskey recommends the beef and broccoli dish. It’s a colorful array of wagyu beef, broccoli puree, water chestnut, oyster, cashew, pickled broccoli stem, broccoli "couscous," and fermented black-bean oyster sauce. It's so darn pretty, you'll be talking about it all night. Oh, and did we mention it's delicious?

Better To Avoid: Although delicious, the bar menu's burgers can be messy — not what you want to eat as someone you just met is staring you down, McCaskey says. And, whatever you do, steer clear of the "Hardee's" burger: It's covered in mushroom ragout.
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Photo: Courtesy of Derek Richmond.
Chef Tony Quartaro, Formento’s
This cozy Italian restaurant, situated in the Fulton Market District, offers a blend of traditional family-style favorites and new American-Italian creations.

Best Bet: "Nonna's relish tray is a great way to begin, as you get to experience six different small bites," Quartaro says. It comes with bagna cauda stuffed olives, melanzane agrodolce, rinforzo salad, radicchio ripieno, sweet potato cannoli, and ligurian beets. "In case you have nothing else to talk about, you can discuss what you enjoyed most."

Better To Avoid: The canestri with Sunday gravy and chicken Parmesan are pretty heavy for a first date, he says. And, since they could leave you feeling stuffed, you might also want to skip this on the third date, too.
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Photo: Courtesy of bellyQ.
Chef Bill Kim, bellyQ
A fun, imaginative take on the traditional Asian barbecue restaurant, this spot even has a karaoke den — in case you and your date get really adventurous. Bonus: It’s a supporter of Step Up, a Chicago charity that works to empower young girls, so you can score brownie points while chowing down on meat.

Best Bet: Dine at a grill table. You and your date sit at your own table for two and the servers prep you with everything you need (ingredients and cooking tips alike) to prepare a three-course menu that changes daily, Kim says. Even if your date is lame, the meal will still be awesome. Sound like too much of a commitment? Opt for the tea-smoked duck breast. After marinating for 24 hours, it’s steamed over tea and herbs for a subtle, smoky flavor.

Better To Avoid: "The baby-back pork ribs. They come in a homemade rosemary hoisin barbecue that's irresistible saucy goodness. It can only be described as finger-licking good, and that's exactly what you'll do," he says.
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Photo: Courtesy of Cafe Ba-Ba-Reeba!.
Chef Matt Holmes, Cafe Ba-Ba-Reeba!
Tapas are about as close as you can get to foolproof on a first date. Hit up this Lincoln Park hot spot, order a ton of items, and you are both bound to find something you like.

Best Bet: Tapas within tapas: The chef's artisanal cheese selection and the plato de la casa, with serrano ham, salchichón, chorizo, and manchego, are perfect for giving you lots of options. Plus, they won’t leave you feeling like you’re about to bust the seams on your dress.

Better To Avoid: This shouldn’t come as any surprise: the garlic potato salad and the shrimp with garlic. "If you choose to ignore my advice, there are mints at the host stand on your way out," Holmes says.
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Photo: Courtesy of Star Chefs.
Pastry Chef Anna Posey, The Publican
Every Chicago foodie knows and loves The Publican, and you can't go wrong at this James Beard Foundation-award-winning restaurant. Plus, if the date goes (really) well, you may even end up holding a wedding here!

Best Bet: "The Vacherin is so light and delicious, but still complex," Posey says. "It's basically an ice cream cake. The 'cake' layers are vanilla ice cream and sweet-tea ice cream, sandwiched between a salty almond meringue. It's topped with tangy kumquat slices, orange olive oil, and roasted almonds. It's the perfectly sweet dessert to end an evening.”

Better To Avoid: "I have an amazing blue cheese on right now from Minnesota. We love it, but it might be a bad choice for a first date," Posey says.
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