Kevin Connolly’s Really Into ‘He’s Just Not That Into You’

In Entourage, Kevin Connolly’s character “E” stays busy managing the career of childhood friend and star Vincent Chase. Week after week, he navigates the treacherous waters of Hollywood, dealing with Vince’s ego-driven agent Ari and his tough-as-nails publicist Shauna. But in his latest project, Connolly enters the most treacherous waters of all — the dating pool. He’s Just Not That Into You (based on the bestselling book of the same name) boasts a cast of Hollywood heavyweights: Jennifer Aniston, Ben Affleck, Drew Barrymore, Jennifer Connelly, and Scarlett Johansson, just to name a few. I spoke with Connolly about the new flick, his worst date ever, plans for the future, and more.

Tell me about the character you play in He’s Just Not That Into You. Connor is an up-and-coming real estate agent who is at that point in his life where he is looking to settle down. He is head over heels for this girl played by Scarlett Johansson who, at the end of the day, doesn’t feel the same way about him. While he looks good on paper for her, it’s just not sort of there. The name of the movie is He’s Just Not That Into You, but Connor is the only one where she’s just not that into him.

How did you prepare for this role? When you are going into work with such heavyweights, the preparation was just being prepared. You want to know your lines, know what the scene is about, and feel like you belong. I just did my best not to be the weak link in the chain because there are some real actors there — Jennifer Aniston, Jennifer Connelly, and the list goes on and on.

Do you feel there are any similarities between Connor and your character “E” on Entourage? Obviously, when you’re on a TV series and people know you in a certain role, it’s a concern you have when you do another project to not feel like you’re watching your character on the show. Personally, from a selfish standpoint, that was one of the things that I was most pleased about with the movie. I didn’t feel like I was watching E. Now, it’s not like I have an eye-patch and a walking stick — I obviously look the same. But I think that it is different enough.

Did you read the book that the film is based on? I had a high awareness of the book. I had an ex-girlfriend who had the book on her nightstand. We would lie in bed watching television, and she would be reading it and would start asking me weird questions. I said to myself, “What is she talking about? I got to take a look at this book.” So, I had read a little bit of it before the movie came around. When I got the role, I went through and read the whole book.

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Your co-stars are the beautiful Drew Barrymore, Scarlett Johansson, and Ginnifer Goodwin. Was it really hard to go to work every day? It was a pleasure. On my first day, I had to kiss Drew, which was fun. The first day that I worked with Scarlett, we had a post-sex scene in bed. By the way, that’s not all it’s cracked up to be. I was a nervous wreck. Strangely enough, I couldn’t wait for it to be over.

In the movie, there are many tech references like “MySpace is the new booty call.” Do you think technology has made dating easier or more difficult? It’s really so debatable. I’m 34 years old and, and when I first started calling girls you couldn’t even leave a message. You called them and either got them or you didn’t. Now, there are some safety nets that I don’t have a problem with, like the “icebreaker text.” But I do believe that you have to move on from the text pretty quick. I think if you really want to get anywhere with a girl, you can only do so much texting. You have to fire in the call rather quickly.

What do you think are the top three reasons of how a guy can show he is not into a woman? 1. Not calling. 2. Not bringing her around your friends and family. 3. If you skip the holidays. If she doesn’t get the invite to Thanksgiving, that could be a big one.

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Have you ever just not been that into a woman? Yeah. Sometimes the bottom line is that if it’s just not there, then it’s just not there.

What was your worst date ever? Years ago I went on a date to a bar. We had some food and a couple of drinks. When we were leaving, we got pulled over, and she got locked up for a DUI. I felt so bad.

Did you bail her out? I tried to bail her out! But it was Memorial Day Weekend, so there was a logjam of people in jail. It wasn’t easy. I tried to bail her out. I made the calls.

What’s one big turn-off for you by a woman you’re dating? I don’t know if it’s a turn-off, but I certainly need a woman in my life that likes sports. She has to be able to sit through a full Yankee game, especially on TV.

One big turn-on for you? I like a girl that can dance.

Do you feel that He’s Just Not That Into You speaks the truth about relationships these days between men and women? Yeah. It could make for some interesting conversation on the ride home for a couple after seeing the movie.

What do you hope that people will take away after seeing this film? It’s not a chick movie. It’s definitely a movie that guys can go see and enjoy. By the way, I didn’t know that at until I walked out of the screening. The first thought I had was that the movie was not a chick flick, which is cool. Not that there’s anything wrong with chick flicks. It’s a great genre of movie, but this isn’t one of those. In terms of what people will take away from the movie, I think that it’s great water-cooler talk.

You’re a successful television and movie star. You’ve directed music videos, commercials, and film. What would you like to do that you haven’t? That’s a good question. I’ve been acting for 30 years, and as an actor you make a checklist of things. The one thing I really haven’t done is theater. I know that it’s a grind, and it’s not something I am looking to do right this second. Eventually, it would be great to do a good run on a Broadway show. It would definitely be very challenging, but I think down the road before I retire from this business that would be something that I would like to take a crack at.

It’s been highly reported that E and Sloan are back in each other’s lives on Entourage. Do you think this is a friendship or a relationship or, in the end, E’s just not that into her? Sloan is back in a big way. There is sort of that friendship, but not really friendship kind of thing going on. And there is another girl in the picture for E, so there is kind of a little love triangle thing happening. I am really excited about my storyline this year because the new season of Entourage is less business-based and more relationship-based for all the characters across the board. It’s more about personal relationships and less about chasing a big movie.

At the moment, you seem to be choosing some great roles. The good thing about being on a successful TV show is that you don’t have to work for the sake of working. For me, it’s a matter of a) waiting for something that I want to do, and b) waiting for the right project. I was so fortunate to do He’s Just Not That Into You. I did a couple of scenes in Katherine Heigl’s movie The Ugly Truth. I just want to continue to try to do the best stuff I can. And if the best stuff isn’t there, I’d rather work on my golf game.

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