Before getting into broadcasting you played football for the University of Colorado Boulder. Why journalism?

I knew I wasn’t going to play professionally. My twin brother did, but I knew I wasn’t going to be able to play at that level so I wanted to do the next best thing which was talk about it. Little did I know it’s not the next best thing. It’s a great job, but it is very demanding and there is definitely a burnout factor. I think there is a burnout factor with whatever you do.

Where was your first reporting job?

I started right out of school at 22 years old. I got my first job in Great Falls, Montana if you really want to go that far back. There was more livestock than human beings! You didn’t know whether to laugh or cry when you looked at your paycheck.

Do you remember the moment you found out you got the job to co-host ABC 7’s “Windy City Live”?

I remember exactly where I was at. I was at spring training covering the Cubs and my general manager called me. She doesn’t call very often so when I picked up the phone I was thinking, “I’m either in trouble or I got the job.”

Who was the first person you called to share the good news?

I couldn’t say anything! When my general manager called me and said that they would like me to co-host the show I said, “Absolutely! Can we talk about the money?” [Laughs] Then when we agreed on the money she said I couldn’t say anything for a couple of days. It was the hardest thing not to tell anybody. The story broke in the morning which was earlier than they wanted it to. It was on the front page of Yahoo in the Midwest with my picture and Val [Warner]’s picture and it said, “Oprah, here are your replacements,” which I didn’t like. I wanted to downplay that as much as possible because– let’s get this out of the way right now– there is only one Oprah.

What was it like getting that kind of national exposure for the first time?

I had a million phone calls and text messages to the point where I returned every single text message, but it took me four or five days. I’m talking people who I went to grade school with that I hadn’t talked to in years.

Ex-girlfriends reaching out?

A lot of that too! I didn’t have a problem getting a date at all after that. [Laughs]

Have you ever had any embarrassing on-air moments?

I’ve had a lot of embarrassing moments. Thank God the only thing on YouTube is the kiss with Jenny McCarthy from a couple of weeks ago.

Windy City LiveWindy City Live

How was it getting to kiss Jenny McCarthy?

Every friend I had across the country was envious. It was incredible actually because it was really… It was interesting because… See, I’m at a loss of words now! I covered sports for so long that no matter how many athletes you met there were only maybe a few athletes where you’re like, “Wow, that’s really Michael Jordan.” Other than that they just become regular people so you didn’t get starstruck anymore. Jenny was this goddess when I was in high school. It was Pamela Anderson and Jenny McCarthy and there was always the debate on who was sexier. When I was told she was going to fill in on the show I thought about MTV’s “Singled Out” and then for some reason there is this image of her squirting the hot dog with mustard. I think she’s very Chicago; she’s not pretentious. She says she hates L.A. and everything that L.A. stands for. She was telling me she could see herself moving back here.

Tell us something about Val that nobody knows.

That’s tough. I don’t want to divulge anything that is going to get me in trouble! Val has a lot of guys who really want her and they tend to think if they get in with me that I’m going to hook them up. I just have to break the news to everybody that she is engaged to be married.

You and Val have great chemistry on air.

We’ve developed a brother-sister type of relationship which is great. I remember when I first got the job my Dad was like, “Ry, you better not, you know, date her or anything like that,” and I’m like, “Dad! Don’t worry about it!” Now we joke about stuff like that because we really are like brother and sister.

Are you single?

Single and dating. My mother wants to know why I’m still single at 34.

And what do you tell her?

That’s a good question. That’s a complicated question. You know, I think it’s because I’ve been so career-driven. I know that sounds like a joke, but I’ve been so career-driven that sometimes I’m not the best at dating. Let’s just put it this way… I’m in no hurry to get married.

When it comes to dating, what’s your biggest turn off?


Where do you like to hang out?

This is one of my big spots; I really like Rockit. I don’t like the club scene. Studio Paris is about as much of that as I’d ever want to do. I don’t like [EDM] music with no words; I don’t really know what that is. I like a good bar. I love a piano bar too.

Are you a picky eater?

Yeah. The thing I cringe about most on the show is the cooking segments because I always have to try something that I know I’m not going to like.

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

Oh, that’s easy. Elvis Presley. I’m a huge Elvis fan. If I could die and come back as anybody it would be Elvis.

Windy City Live
Photography by Neal Agustin

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