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How did you coin the term ‘cheeky’?

After we came up with the idea for the website we decided we wanted Chicago in the name because we wanted it to have a very local feel. I thought, “There has to be alliteration! I just have to have it,” and literally I just spit out the words ‘Cheeky Chicago’ and Jessica was like, “Oh my God, that’s it!” We loved the word cheeky because it’s so underutilized. The definition we found that embodied it was definitively bold, impudent and saucy. That’s exactly what we wanted it to be.

Did you know you were onto something big?

I think when you start something you have to think it’s going to be something big otherwise, what’s the point? We wanted success and we realized there was really nothing else out there like it. There are a million city guides and there are a lot of female-focused websites but there was not a city-centric, female-oriented guide or magazine out there that combined both of those things. Jessica and I, as the demographic of who we wanted to capture for CheekyChicago.com, didn’t have that resource so we thought we would create it.

You recently celebrated CheekyChicago‘s third anniversary. How does that feel?

It was surreal in the sense that they say if you can sustain a business for three years you are pretty much, not good to go because there are a lot of things that could happen but it’s a really good place to be. It was a huge milestone for us, it’s very exciting.

Do you attribute Cheeky’s success to your friendship with business partner, Jessica Zweig?

The basis of what CheekyChicago.com really is about is women helping women. It’s about fostering a community of women, helping one another out, becoming more friendly and less competitive. If we weren’t friends our whole business wouldn’t survive because that’s the foundation.

Cheeky Chicago

You’re a big foodie. Being Chicago’s staple, what is your favorite pizza place?

I love Gino’s East for Chicago pizza. Oh my gosh, Gino’s is the best. It’s the cornmeal crust and the sauce ratio that makes it really good. I love La Madia for a more upscale, flat crust. And I love Quartino’s pizzas, I think their mushroom pizza is the best.

Favorite place for a night out?

Naha is one of my favorite places. I’m biased because my boyfriend is the general manager but the chef, Carrie [Nahabedian], is one of the very few James Beard Award-winning chefs in the city. From a culinary standpoint, it’s one of the best for sure. The bar gets really lively at night so it’s really a fun, high-end experience.

How did you meet your boyfriend, Terry Kane?

We met on the 22 bus. I was standing on the corner of Armitage and Clark waiting for the bus and this guy drove around the corner with his convertible top down and was yelling from the car. Terry used that as his way to talk to me. He goes,”That guy is crazy!” and then we just started talking. I do believe in fate because he was actually walking to work that day, which he never does. In the three years we’ve been together he’s never walked to work. So single people, take the 22!

If you could have a drink with anyone, who would it be?

As an actress, I would hands down pick Susan Sarandon. I love everything about her. I could say so many people. Liza Minnelli is my absolute favorite. That’s so dorky of me but I absolutely love her. Robert Downey Jr. I should probably name more intelligent people, like presidents or something! I would love to meet Bill Clinton. Princess Diana. That’s good. That’s a good list.

Cheeky ChicagoPhotography by Natalie Probst

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