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.
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.
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