We hope you need a cocktail.

Oh, I need one! I was actually dressed up but then I was like, “I’m getting comfortable!” This is the happenin’ spot, it’s gorgeous!

Since you’re staying at Dana Hotel, there’s no better place to have a drink than Vertigo Sky Lounge.

You mean 10 drinks? What are we sipping?

We heard you like your drinks spicy so we’re having Red Stag by Jim Beam® cocktails.

Okay, done and done. This is so fun! Cheers! This is the highlight of my day, I swear. Mmm, is this rum?

It’s a different breed of bourbon spiced with cinnamon.

Oh, damn! We aren’t messin’ around. I love it!

What do you remember most about heading into E! for that first audition?

Oh my God. I was really nervous, you guys. I had done hard news and been in a newsroom but the funny thing is I had always kind of felt like the black sheep because I was the one chick who wanted to cover fashion and celebrities or movies and music. In a real newsroom that’s the easy fluff work while they’re out doing “real” news. I wanted the job so badly and I remember being really nervous. I’m pretty sure I did a shot beforehand! I remember walking out of that first audition, calling my mom and brother then going, you know what? I killed it! So whether they want me or not, whatever is meant to be will be.

Did it take time to learn how to navigate the celebrity interview?

In my early days at E! I was pretty young. I was in my early 20s at the time and nobody tells you how it works, there is no manual so you’re asking the questions and you just go with it. Now having an inside perspective, the most interesting thing about celebrity interviews that the rest of the world maybe wouldn’t understand is that it’s never the one-on-one you think it is. You walk into the room and there’s the movie studio publicist, their personal publicist, there’s a team of 15 people that are looking out for them so you always kind of feel like you’re on the other team and you have to be careful and navigate. It’s definitely an art and I think that is probably what makes people good at what we do. At any given moment you have to be able to roll with any scenario and attitude or personality and mood.

What’s the key to maneuvering the different personalities you encounter working in the entertainment biz?

Hollywood is like a disease for some people. It does things that other people will never have to experience. I know a lot of people don’t have sympathy for some celebrities like, “Hold on. You’re rich, you’re famous. Really?” But then you see what happens. Nobody’s real with people, nobody tells them no, there’s a lot of that that goes on so I understand and make allowances for people. You can interview someone and on any given day they’ll be a different way. Sometimes we have good days, sometimes we have bad days. Sometimes I’m my best self, sometimes I’m a lousy version of myself so I would hate to walk away from an interview and make a whole judgement on who they are as a human being. I try not to take anything personally because who knows what he or she is going through. I really respect the Johnny Depps of the world who walk in the room and look everyone in the eye and say hello to the crew, say hello to the camera guys, say hello to the producers. I dig that, man. There’s a reason certain people are A-list. They get it.

After forming friendships with the people you interview, are there times you have to choose between breaking a story and keeping quiet?

Yes. There’s nothing scandalous about this but I’ll give you an example. I was flying from L.A. to New York just a couple months ago and randomly—trust me this doesn’t happen all the time—E! was like, “We’re gonna fly you on a private jet.” I was like, “Okay! Indiana girl on a private jet! Rough day on the job!” [Laughs] I didn’t know who else was going to be on the plane but I get there and it’s Kim Kardashian, her mom Kris Jenner, Chelsea Handler, Ross Matthews… and me. I was thinking, “Should I be pouring the drinks and serving the food? How do I fit into this?” But Kim is very pregnant and has all of this going on in her life. She is, by the way, one of the nicest people you will ever meet. She’s so awesome. We ended up having this really cool girly conversation. I’m a mom, I have two kids so she told me how she was feeling, how much weight she had gained and she wasn’t editing herself. I could have run to E! and said, “By the way, she’s gained this much and this is what she ate,” but I couldn’t do that. I wouldn’t do that. You have to find that divide. We had a lot of conversations where I thought, “Is this for real?” but that shows how cool she is. I appreciated that because a lot of people shut down when they see people like me who work for E! because they think we’re gonna go run and tell all the goods.

You married your husband, U.K. producer Rhys David Thomas, almost two years ago. Did you make it a point to not date within Hollywood?

I’m still waiting for Ryan Gosling to ask me to marry him, are you kidding? Dang! But I never made it a point actually. I’ve dated people in the industry and actually my husband works as a producer in the film industry but he’s in finance and not really on the artsy creative side. I will say though that I’ve never been in an interview and given my card or shared my number at work. And I know some people who do that. Trust me, I’ve certainly flirted with actors and they have with me, by the way! I’m proud to say! [Laughs] But in the midst of working that has never gone down, ever. And it goes down. A lot of girls I know are like, “Call me later!” and good for them but that has never happened to me.

What was it about your hubby that won you over?

It was one of those situations where we were at a place kind of like this, not gonna lie, on a Monday night. It was Cinco de Mayo and it was a charity event, one of my friends was DJing and we spotted each other across the room early in the night. It took until later in the night before we actually talked. He says I came up to him and I say he came up to me, it was one of those things. But I loved his transparency. I think there are so many people who play so many games and there’s the whole, do you text? Don’t you text? What do you say? How long do you wait? All of that stuff, that has never worked for me. I just don’t have time for that. He was incredibly forthcoming and authentic. He was like, “Oh, your name’s Catt? I have three cats!”—first of all that’s weird but okay, we forgave you for that—and then he said, “My brother’s girlfriend’s name is Catt!” There were all of these little things that were funny in the beginning but the truth is that I sensed we had a real connection. I’ve always prided myself on just being very much “what you see is what you get” and he was that way too.

How did he propose?

Well, that wasn’t the most romantic part. Mind you, I was married once before so for me this was kind of phase two in my life. I have two kids and my ex-husband [Kyle Boyd] and I are absolutely great friends. We were college sweethearts and got married really young, that chapter was over. Rhys is British and was living in London at the time. He was traveling back and forth and we were falling madly in love. We knew we wanted to be together but in order for him to even stay in the country we had to get married, like tomorrow! We knew we were going to get married but we were like, “We gotta get this goin’!” For one, so he could work in the film industry in Los Angeles and two, for him to be able to stay more than two months at a time. So we were like, “Should we just go to Vegas? Should we just do it?” And we did! I never thought in a million years that would be me. But it wasn’t about the production, it wasn’t about the dress and the ring. I did that once and every girl should or could or whatever, I’m down with that, but for us it was just us on the 50th floor of the Palazzo in Las Vegas. We had champagne and candles and it was really intimate. I’ll never forget it.

Have your two boys, Arion and Austin, started to take note that their mom is on TV?

They get it. It’s funny now they play on it because they know how embarrassed I get. We’ll be in the produce section of the grocery store and they’ll say, “Look, it’s Catt Sadler!” and I’ll be like, “You guys! Seriously. Stop it!” Then people will look up. Which, by the way, 99 percent of people don’t even know what that means but the boys get such a kick out of it because I get so embarrassed. We just went on a trip to Barbados for spring break and it’s a small country so they only have maybe 11 channels and E! is one of 11 channels so it’s all anybody watches. You would have thought I was the president, it was crazy! My kids were like, “Um, what’s going on?” I was like, “I don’t know but this is awesome!” [Laughs] Everyone was so nice. It was really cool! Very odd, but cool.

What’s one part of your day that you wish you could eliminate?

We do a lot of voice over work. You’ll see us in the studio when we’re on camera, you’ll see us in the field doing the reporting for the stories and I like the voice work a lot actually but the tricky thing about doing news and also the cool thing is that we try to be current. I might track a story at 10 in the morning but we don’t film until 2 and the story might change four times if so-and-so tweets or so-and-so breaks up. So you have to go back and forth to the voice over booth all day. That’s a little annoying. The producers say, “Come back for a re-track!” and you’re like, “I was just there!” That would be the only thing I would eliminate. I’d like to only do it once!

When you’re working in such a fast-paced industry, do you make it a point to sit back and take it all in? 

This tattoo right here is about that very thing. It’s my reminder to focus on the moment. This [on the left] is the past and, eh, that’s over and this [on the right] is the future and we don’t know if we have tomorrow, right? So I like to see this because it just reminds me to be very present. I do pinch myself often because I love my life, I love my job and then I look at my family and everybody’s healthy and everything’s cool and all that I have is all that I need. I just think practicing gratitude is very powerful. I learned that from Oprah, she was my mentor growing up and I have my gratitude journal.

What brought you to Chicago for the weekend?

I’m here because I’m an integral part of Simply Stylist, which is an event that was started in Los Angeles by my good friend Sarah Boyd. She had this genius idea to bring all of the components of the fashion industry together in one room so we as women, and some men of course, can get together and learn from one another. The whole idea is to really inspire people. Some people are already in the industry and some want to be in the industry but it’s about hearing the real talk of what it takes to pull off and survive a pretty competitive and tough but also glamorous and fun job.

Who has been one of your favorite interviews or people you’ve connected with along the way?

Can I take one sip before I answer that?

Of course, we’ve been sipping.

I’ve got to get a couple more sips in while we’re talking. Then while I talk, you drink! Do you guys have a drinking game with this little segment?

Why have we not thought of that?

You should incorporate a game into your “drink with”. You could ask a question and then you have to hurry and if you don’t answer it right or on time, you drink.

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

And you have to only pick one? It’s so hard!

Have you ever interviewed someone and thought, “I’d like to have a few drinks with this person”?

For sure! But who? Gosh, they all kind of run together, it’s so sad to say. Matthew McConaughey for example; here’s a guy that wouldn’t be my dream guy on paper aesthetically but I find him so intriguing. He’s from Texas, he’s a man’s man. I know he likes his beer and I love that he’s a family guy. I would like to go to drinks with him and talk and get real because it seems like he knows what he’s doing. I twittered one time that I really, really wanted to do sake bombs with Anderson Cooper because I think that he’s so funny and so smart and he’s seen the world. I also feel like he has this responsibility to be on TV and be so perfect and together all of the time so I’d like to maybe give him some shots.

Anderson has to know how to let loose.

Exactly! That would be cool. There are certain girls where I just know we’d be really good friends, you know? There are so many! I’m trying to think of who off the top of my head. I mean, Beyonce duh. But she’s a really busy girl, I don’t even know if she has time for drinks. Michelle Obama is another woman I think is so inspirational and powerful. I am just in awe of people who are smart and intelligent and do really good stuff. Jessica Alba and Gwyneth Paltrow both don’t know that I should be their best friend. They are just so normal! Completely unaffected.

KIRSTEN MICCOLI PHOTOGRAPHY