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Casting The Film
From the very beginning, the filmmakers saw "The Last Kiss” as an "actor's film,” one that was filled with interesting roles that attracted the interest of some of the finest young talents. As Goldwyn recalls, "When we were casting the movie, the actors in their 20s that we saw said to me, ‘It's so amazing to read a script that is honest about what it's like for us trying to figure out this relationship thing.' They told me they'd never read a script that doesn't cutesy it up, idealize it, or dump on it. It reinforced that we could make a film that is a very loving, but painfully honest look at the ridiculous struggle that we all go through as we come of age.”

For Goldwyn, casting was essential – the actors they hired would determine what the final film would be like. "There's sort of a group of 29-year-old guys who are out there in our pop-culture actor sphere,” explains Goldwyn. "But every time a name was brought up, the actor just didn't seem right to me. And then when Gary and Tom mentioned Zach Braff, I said, ‘That's the movie you want to make.'”

The reason for that, according to Rosenberg, is that Braff is an actor who is adept at eliciting sympathy from the audience. "It was a difficult line for Zach to walk in the role and he does things that audiences normally won't forgive,” comments Rosenberg. "Michael has to be likeable and sweet, but without saccharine. There aren't many actors who could do this role; Zach knew it was a great role for him and he played it perfectly.”

In fact, Braff was the first choice from the very beginning. "He's a very interesting actor,” Lucchesi says. "The role calls for him to be funny with the guys and charming with women, but also serious, focused, tender, loving, and committed in his scenes with Jenna. Zach is absolutely convincing.”

Goldwyn says that casting Braff helped him frame his vision of what the film would be "Zach Braff gives the film an identity in terms of reality,” he says. "He's a real person; he also has a very distinct kind of wit and sense of humor, as well as intelligence and an offbeat quality. He makes you feel that there's a real guy on the movie screen, but of course, he's still a leading man.”

Braff was particularly drawn to the ways the role rang true to real life. "I just turned 30 and was starting to ask the same questions of myself that Michael asks: what do I want my 30s to be like? How do I imagine my life going? The characters in this film are all in a period of self-examination. I think all of us in the cast found something in common with the characters we played.”

"Michael's in love with his girlfriend and has great friendships, but he's a little afraid the surprises are going to stop coming in his life,” Braff continues. "He's terrified that the rest of his life is going to be programmed out according to all the societal conventions. When he panics and runs back to the freedom and innocence of being in his 20s, he finds that his choices have consequences that didn't exist five years earlier.” 

One key to the role, for Braff, was making each relationship in the film seem real. Not least of these was the relationship between the four guys: Michael, Chris (Casey Affleck), Kenny (Eric Christian Olsen), and Izzy (Michael Weston). "These four guys have known each other forever – when I talk about ‘The Last Kiss,' I often describe it as a modern-day ‘Diner,' a film about a group of friends at a crossroads who are all going through the same thing,” says Braff. "It was important for the four of us to bond, and it was easy, because all of us got along so well.”

Braff felt it was equally important to portray a real relationship with the two women in his life – Jenna, the mother of his child, and Kim, the woman with whom he has an affair, played by Jacinda Barrett and Rachel Bilson, respectively. "With Michael and Jenna you see that there is this great love

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