The Coolest First Date Spots in Chicago

When it comes to a first date, the setting is just as important as your ability to blanket insecurities. Pick a place that's too intimate and you'll look like a desperate Bryan Adams song personified. Choose a spot that's too casual, like the drive-through window of a Carl's Jr., and risk having your Match.com profile flagged for scrubism.

To help our Chicago area daters with that all-important first impression, we've amassed a carefully curated collection of can't-lose, first date spots.

Written by Sean Evans (@seanseaevans)

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Neighborhood: Near North Side
Address: 435 N. Clark St.
Website: threedotschicago.com

Three Dots And a Dash is a tiki themed bar without the cheesy, bamboo-ridden tastelessness of a Jimmy Buffet concert parking lot. This joint has an endearing novelty that makes transitioning between conversation topics easy, which is an absolute luxury during a first date. Like, if you get caught up in a 25-minute-long soliloquy about her CrossFit WOD or how her cat "totally sits on the couch like a person," you can point out the bar's smoldering, punch-filled treasure chests and say, "Whoa, those are cool. Right?" Then, you can interject with a breakdown of your fantasy football team. Just joking. Ask her about her job or whatever.

As an added bonus, this place is sandwiched between Bub City and Paris Club, which are perfectly worthwhile places to keep a good date going, or—if things aren't going so hot—ideal spots to salvage what remains of your Saturday night.

Neighborhood: Lincoln Park
Address: 2001 N. Clark St.
Website: lpzoo.org

First, the Lincoln Park Zoo is totally free to enter, which is a plus for those of you with a Wesley Snipes-like credit limit. Second, it's in the middle of one of the most trafficked parks in the city. So, if you're getting Catfish-ed on Tinder by an ex-con with a violent criminal history, your rendezvous will have hundreds of eyewitnesses.

Besides those first date fundamentals, the Lincoln Park Zoo has a comprehensive animal catalog. Its free-99 price tag might lead you to believe that it's a chain-link storage container with two pygmy goats and a sickly ostrich, but it has a veritable Noah's Ark of wildlife, including lions, gorillas, and polar bears.

Neighborhood: Pilsen
Address: 2119 S. Halsted St.
Website: nightwoodrestaurant.com

To take a date to Nightwood is to say, "I cried at the end of Terminator 2: Judgement Day, but I've also slugged a guy in a mall parking lot for stealing my space." The dining room is more intimate than casual, but it's not so flagrantly romantic that you come across like a hopeless thirst bucket. Nightwood will represent you as the refined adult that you're probably not, which is precisely what you're looking for in a first date spot.

Neighborhood: Lakeview
Address: 3155 N. Broadway St.
Website: dryhopchicago.com

If you're on some third date vibes with an ardent ale drinker, we highly recommend the Half Acre Tap Room. But DryHop Brewers is a craft beer alternative that isn't quite so niche, mostly because of the small plate and full bar options. You can't go wrong by mixing innocuous small talk with a flight of in-house brews; that's the kind of disarming blend that guarantees a second tryst.

Neighborhood: Lakeview
Address: 2833 N. Sheffield Ave.
Website: hqbeercade.com

You have to be careful when picking a bar in the Lincoln Park/Lakeview area for a first date, chiefly because you might walk in on a wristband-fueled shitshow. In sum, bro-to-bro haymakers and sticky pub floors make for bad first impressions. But Headquarters Beercade, a recently expanded arcade bar in Lakeview, is a digitized reprieve from the usual north side debauchery. Headquarters vaunts wall-to-wall retro video games that are free to play, and a pretty expansive cocktail menu.

[Pro tip: Keep your head during a friendly game of NFL Blitz with your date. After taking the lead with a late game touchdown, don't spike your beer like a pigskin in the end zone and deliver an profanity-laced tirade against your opponent. It's bad form.]

Neighborhood: Lincoln Park
Address: 2624 N. Lincoln Ave.
Website: barrelhouseflat.com

Chicago has more than a few places to sip cocktails and table talk (The Violet Hour, Billy Sunday, and The Whistler for example), but The Barrelhouse Flat has a distinctive second floor that elicits an almost palpable sexual energy. If Humphrey Bogart were to go on a first date with Mae West, they'd definitely drink cognac-based cocktails at this joint.

The Barrelhouse Flat has a more casual atmosphere than, say, The Violet Hour, but it's not the type of place to rock a salsa-stained Derrick Rose jersey. Dress nicely and, for the love of Based God, don't sip your drink from a straw. You look ridiculous.

Neighborhood: West Loop
Address: 564 W. Randolph St.
Website: embeya.com

Embeya, one of Esquire's "Best New Restarurants of 2013," is almost too palatial for a first date. This place has all the understated charm of a Saudi oil prince's walk-in closet, so come correct with how you represent yourself (read: don't pick her up in a rented Plymouth Prowler whilst reeking of Old Spice body spray). That said, Embeya is a visually stunning, toothsome addition to the West Loop's already revered collection of restaurants. If you need awe-inspiring scenery to compensate for your lack of social skills, this is the culinary equivalent to a sunset on the beach.

Neighborhood: Near North Side
Address: 11 E. Ohio St.
Website: acmehotelcompany.com

The Berkshire Room is a swanky lounge in the ACME Hotel, and the perfect spot for gin-fueled canoodling. Typically, hotel bars have a shady connotation that you wouldn't associate with a first date, but this place is as amiable a spot as you'll find downtown. Go for the Dealer's Choice—a DIY drink option that puts a cocktail's spirit, flavor profile, and glassware in your hands—because it's the perfect opportunity to kittenishly debate your new plus-one.

Neighborhood: West Loop
Address: 840 W. Randolph St.
Website: maudesliquorbar.com

Maude's Liquor Bar is the first date spot of choice for debonair gentlemen who own artisanal shaving kits and drink whiskey that's aged in an oak barrel. Rock a varsity cardigan and some shoes without glow in the dark soles to this Brendan Sodikoff haunt, and you'll look like you have Cary Grant-like acumen, even if you're some twenty-something bozo with an X-Box Live addiction.

Neighborhood: Logan Square
Address: 2051 N. California Ave.
Website: bangbangpie.com

For whatever reason, "grabbing coffee" has become the informal first date agenda of choice for unimaginative dudes everywhere. We're not saying there's anything wrong the uber casual Starbucks setting, but no one has ever found love in that hopeless a place. Instead, meet for pie because everyone loves pie. And go to Bang Bang Pie Shop because everyone loves Bang Bang Pie Shop. Also, pie dishes really shine on Instagram, and she'll appreciate a guy who knows how to elicit a "22 likes" banger. That's the 2013 hallmark of a gentleman with sophisticated taste.