9 Awesome First-Date Spots — Chicago’s Experts Dish

You've got a date? Super. The rest should be a cake walk, right? Not so fast. We've all experienced first-encounter blunders — from no-show nightmares to awkward silences — probably more often than we'd care to admit. And while stepping out doesn't come with an insurance policy, there are a few things you can do to go into that initial meet and greet with total confidence.
But, don't take our word for it. We tapped three local experts in matters of the heart, who know more about navigating the world of Chicago dating than your BFF and mom combined. Doling out a medley of useful tips, these doyens of devotion divulge the coolest places to go on a first date in this great big city of ours, plus so much more. Now, what are you waiting for? Your complete guide (and hopefully your true love), awaits.
Stefani Safran, Stef and the City
Safran has 10 years of professional "love connection" experience, including a stint as a contestant coordinator on the Dating Game and working at one of Chicago's top match-making firms. She now has her own business and has been showcased in the press and on television countless times for her expertise.

Top First-Date Spots

1. "The new wine bar Flight 1551 offers a nice atmosphere for wine and conversation. If the weather permits, they also have great outdoor seating. And because it's small and intimate, you can have a comfortable, private conversation."

Flight 1551 1551 North Wells Street (at North Avenue); 312-944-1551.

2. "Take a walk down on Wells Street in
Old Town
! A first date, these days, should be simple. Many people prefer to save a dinner date when they know that they want to spend a second evening with their date. Old Town offers alternatives such as dessert shops, a plethora of bars (like Benchmark), and comedy clubs like Zanies and Second City."

3. "If you want to hit up a place on the way home from working in the city, Quartino tends to be a GREAT place to meet up for pizza and wine. Besides the hip atmosphere, the dishes are Italian tapas and very reasonably priced. Quartino has a great vibe for all ages, whether you are in your 20s, 30s or 40s."

Quartino, 626 North State Street (at Ontario Street); 312-698-5000.

Stefani's First-Date Dos And Don'ts

1. "Every date is a first impression. Even if you’ve gone on a million bad dates, the next one could be the right person."

2. "Make sure to put time into getting ready and try to be relaxed."
3. "Be prepared to have non-defensive answers if you get asked an uncomfortable question."
4. "Don’t interview; the bottom line is that it takes time to get to know someone regardless of how they answer your questions on the first date."
5. "If the person fits 85 percent of what you are looking for, give them a second date. Many clients tell me that the best relationships they have been in, they didn’t have that instant “wow” factor on the first date."

Texting Versus Calling

"I have a three-week no-texting rule. Texting takes out the cues we need to understand people. If someone starts texting you, it’s simple of how to correct this: Call them and let them know you don’t like to text and you prefer to be called. If they don’t follow what you’ve asked for this early on, then they are not the right person for you!"

Photos: Courtesy of Flight 1551, Quartino, Benchmark, and Second City.

Barbie Adler, Selective Search
Adler is one of the biggest names in the biz — and not just in Chicago. Her unique "executive personal recruiter" approach has given her credibility with everyone from The Wall Street Journal to Self magazine — not to mention countless happy couples.

Top First-Date Spots

1. "Balena has a post-industrial Nuevo modern appeal. Come here for some great wine and amazing flatbreads before seeing a show at the Briar Street Theatre."

Balena, 1633 North Halsted Street (between North Avenue and Willow Street); 312-867-3888.

2. "I love how Nellcote manages to be upscale and beautifully appointed inside while offering a menu that is down to earth and easy to share."

Nellcote, 833 West Randolph Street (at Halsted Street); 312-432-0500.


3. "For the best of both worlds, Prasino has a great patio dining and a luxe interior. If you’re sitting outside, it makes for great people watching. Its menu is great for sharing, which is perfect for getting to know your date better."

Prasino, 1846 West Division Street (at Honore Street); 312-878-1212.

Barbie's First-Date Dos And Dont's

1. "Start with a clean slate. Let the past be the past, and look to the present for new opportunities."

2. "Leave a little to the imagination. Guys love a bit of mystery, and it will lead to him wanting to learn more about you."
3. "Listening is just as important as being well spoken. Be engaging, show a genuine interest in his passions, and he will do the same for you."
4. "Don’t forget to smile, and make eye contact."

Texting Versus Calling

"Texting is okay from time to time, but ultimately if he is genuinely interested in you, he is going to call you. Let him know that you prefer to talk versus texting. Conversely, don’t be afraid to pick up the phone and call him."

Photos: Courtesy of Nellcote, Green City Market, Prasino, and Balena.

Bella Gandhi, Smart Dating Academy
Not only does Gandhi run a full-service personal-consulting firm, she's also the head dating coach for Smart Dating. She's known for having an "uncanny sixth sense about people," which has lead to countless marriages. You may have seen her on television or in the paper, dishing advice — The Huffington Post calls her the "Fairy Godmother of Dating!"

Top Dating Spots

1. "Grab a wine flight at Webster's Wine Bar. It's dark, cozy, and has good small plates for sharing. Considered one of the first wine bars in Chicago, it's a nice, classic option."

Webster's Wine Bar, 1480 West Webster Avenue (between Clybourn and Ashland Avenues); 773-868-0608.


2. "For something more new, swank, and sexy, Maude's Liquor Bar is a great option. They have amazing cocktails (like the Smoky Violet), and it's extremely intimate — especially upstairs."

Maude's Liquor Bar, 840 West Randolph Street (at Halsted Street); 312-243-9712.

3. "For a casual option, a sweet treat at Anthony's Homemade Italian Ice on Southport is always great. If it's a warmer fall evening, take a stroll around the neighborhood afterward."
Anthony's Homemade Italian Ice, 3442 North Southport Avenue (at Cornelia Avenue); 773-868-4237.

Bella's First-Date Dos And Don'ts

1. "Be a great conversationalist by staying positive, having fun stories to tell, and most importantly, by being a true and present listener."
2. "Don't talk about how much you can't stand your job, about your strange friends, and never about your exes. In short, leave all baggage at home."
3. "Don't drink too much! You get sloppy and will NOT make a good first impression."
4. "Always take it slow physically."

Texting Versus Calling

"If you are okay with it, it's fine. If you're not, you need to say, 'I'd love it if you called tonight.' If he doesn't respect your wishes, it's probably a harbinger, and he's not worth keeping around."


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