Connick said it wasn’t at all difficult to play a guy who’s a bit of a dork and very awkward around women. “It was very easy to tap into. I didn’t have to tap at all, as a matter of fact. Well, we were dealing with a character who could have been borderline being controversial in that he’s got Asperger's syndrome, and to be funny without laughing at that syndrome was sort of the challenge that Richard had, when I came to the process that I had too. But, you know, this guy just says whatever’s on his mind. I don’t know what you’ve seen of my work, but in personal situations I’m probably more like that guy. I’m really good onstage. I like to get out there and perform for people. But I’m a pretty quiet person otherwise, you know? I think if there was somebody like Hilary that I fell in love with, it would be difficult to communicate with her. It was hard for me to sort of communicate with my wife when I first met her. It’s just intimidating. I would never be a big player like that.”
Playing a character with Asperger’s required a little extra work on Connick’s part. “I knew what it was but I certainly couldn’t have played a character of a guy with it,” explained Connick. “I had to do a little research about that. And subsequently I’ve done more, just because I’ve become fascinated with it. Yeah, but it’s profound. It really is an interesting disorder.”
His character, Dennis, doesn’t filter what he says and at times acts inappropriately, something Connick says happens to people with Asperger’s. Dennis even goes as far as to ask out Holly (Swank) at her husband’s memorial service. “Well, that’s the whole point of Asperger's,” said Connick about Dennis’ lack of social skills. “It wasn’t [too] soon in his mind. He just doesn’t pick up on the social etiquette that normally occurs when people meet. He just says what he has to say, and then has to deal with the consequences which is, from what I know about the syndrome, is probably very debilitating for people with it. The fact that they say things and then can’t understand why they’re being treated the way they’re treated, why they’re looked at in an awkward way… They just say whatever comes to their mind. They’re at the memorial service and he’s hitting on her so I would think that’s too soon. But this guy doesn’t.”
Most of Connick’s co-stars were female and that's pretty fine with the actor/singer. “My life is chick powered. My manager’s a woman. My wife’s obviously a strong, intelligent woman. I have 3 daughters. I’ve got 3 dogs, they’re all female. I’ve got so many women in my life, running my life, I wouldn’t know what to do with a guy so… In fact, I’m probably gay and I don’t even know it,” joked Connick.