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The F Word, a new romantic comedy opening Friday, covers familiar romcom territory – about men and women and friendship (or more). But it does so with a rich contemporary quirkiness, and a Canadian perspective. The film was shot in Toronto – proudly playing itself; directed by Canadian Michael Dowse (Goon); and written by Elan Mastai, who was born and raised in Vancouver. He adapted it from the Fringe Festival play Toothpaste and Cigars, by Canadians TJ Dawe and Mike Rinaldi, which Mr. Mastai saw in Vancouver in late 2004.

It also features a superstar actor in the lead role: Daniel Radcliffe plays the heartbroken med-school dropout Wallace to Zoe Kazan's unavailable (but happy to be friends!) Chantry, an animator.

"I think Elan Mastai … is a very funny, very clever man," Mr. Radcliffe told me during an interview at the Whistler Film Festival in 2012. "He writes women very well as well. Which is I think obviously very important for a romantic comedy."

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Mr. Mastai, 39, is now based in Toronto (where he's now writing a screenplay based on an episode of the radio show This American Life). We reached him in B.C., on vacation with his family.

Where were you in your screenwriting career when you saw that play?

When I was growing up in Vancouver, it felt like more of a place that people from Hollywood came to shoot their movies, but it wasn't really a place where people wrote movies. The idea of being a screenwriter seemed very far away. I didn't know anybody in the business, I didn't have any connections, I was really starting from scratch. So when I was starting out I was very much open to whatever job came my way. I was still in university when I got hired to write my first movie. It was a kids' movie for Keystone, who had done the Air Bud movies; it was called MVP: Most Vertical Primate. That was in late 2000. And in 2005 I'd been working relatively steadily, but it was mostly on work-for-hire jobs. I didn't feel a huge amount of personal ownership over the material; I was more of a hired gun. So The F Word was the first project where I was going to pursue my own voice instead of writing the version that someone was asking me to write.

How did you become screenwriter-for-hire?

This friend of mine from university was working for this producer. She said, I can't get you a job but I can get you a meeting. He often looks to meet with young writers and I can at least get you a phone call with him. The phone call went well and the followup meeting went well and I ended up getting hired to write a draft on this kids' movie. I wrote three drafts in five weeks and every step of the way I assumed I was going to get fired because I didn't know what I was doing. But there was enough raw energy in those pages that I ended up sticking with it and that movie ended up getting made. The funny thing is, I don't think this woman totally explained to this producer that I had never written a movie before. I think he just thought I was a screenwriter who had done some stuff and he wouldn't be on the phone with me if I didn't know what I was doing. My approach was fake it 'til you make it. In fact, I knew so little that I didn't really even know how to format a screenplay. I went to a bookstore and I bought the published screenplay for Pulp Fiction. I modelled my first screenplay off of what Quentin [Tarantino] had done. To the point where Pulp Fiction was 134 pages so I made my screenplay 134 pages – which is way too long for a kids' movie about a skateboarding chimpanzee. In fact, the producer described it as War and Peace with chimps.

Mr. Mastai began writing The F Word in 2005, by 2008 it was on The Black List (the best unproduced scripts in Hollywood). It was acquired by Fox Searchlight, but did not get made by the studio. Then Mr. Dowse and other producers from Goon got involved.

The script for The F Word was in flux for years and next thing you know Daniel Radcliffe has signed on to play the lead. What was that like for you?

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When you kind of step back it seems like a huge deal. But at the time a lot of different names had come up and hadn't worked out for various reasons sometimes about money, sometimes about schedules, sometimes they'd taken another movie that was too similar. These names get floated around all the time. And Daniel's name came up and we were interested and of course we had that fundamental question which was: is he funny? But what we discovered is Daniel wasn't messing around. Sometimes you get actors who voice some vague interest and you can waste months chasing after them and they decide not to do it or they decide to do something else or maybe they'd do it some other time , could you wait for them for a year or two? But with Daniel, he read the script and [later] told me he decided on page two that he was going to do it. Michael got on the phone with him and then flew to London to meet him and when he came back, he said this is the guy. He's totally Wallace. He's hilarious, he's self-effacing, he doesn't take himself too seriously and he gets the character, he gets the script and he wants to make the same movie we do. As soon as I met him I knew he was right for the part. And it's very exciting because you need to get someone who can close your financing and open your movie around the world. You want people to see your movie. He's a movie star and that's fantastic, but more than that, he totally embodied the character much more thoroughly than I had any reason to hope we'd find. Because when I started writing it, Daniel was a teenager doing Harry Potter movies. The idea of him starring in this movie would have seemed ludicrous; I just wouldn't have thought of him in that context. But once we actually met him and got to know him it became impossible to imagine anybody else playing the part. And because he's super famous, that helps.

What was he like to work with?

Mike and I joke that he has more experience on set than pretty much the entire crew combined. He's incredibly gracious and thoughtful. You see that on set all the time. One day we were all sitting around shooting the breeze between setups and we overheard this extra complaining to another extra that she had a splitting headache. And Daniel just goes up to her and he's like, are you okay? He mentioned that he gets headaches sometimes too and he always keeps medication in his trailer; does she need anything? And you should have seen the look on this girl's face. She's just, like, an extra in a party scene and the last thing she expected was the star of the movie to come up and check if she's okay. That's just an example of what he's like.

The film has had its title changed for the U.S. to What If. How do you feel about that?

It wasn't ideal. Obviously I love the title The F Word. I think it captures the kind of cheeky edgy charm of the film. But when we sold it for U.S. distribution they were very candid about it, that the ratings board would have an issue with calling it The F Word. I don't think anyone thinks American civilization is going to crumble just because of a cheeky title. But the honest way I look at it is that most Canadian movies struggle to even get seen on Canadian screens, let alone to get distribution across the U.S. and around the world. So if a title change is the price we have to pay for that, then it's well worth it. The fact that on our side of the border we have this cheeky, more evocative title is unique. And we just take it as a banner of pride – that Canadians can handle it.

I understand there were some changes made to the script – the end in particular.

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We didn't actually change the ending of the movie, but we added an epilogue where we return to the characters 18 months laterand check in with everybody. After screening at TIFF and paying attention to the reaction of the audiences and having conversations with people whose opinions we trusted, we started to wonder if there wasn't a little more closure we could provide the audience. When we sold the movie to CBS Films, our U.S. distributor, they felt very strongly that the movie needed just that little burst of closure at the end; that the audiences had become so invested in the characters that they wanted to know what happened to themin a way that we hadn't laid out quite so clearly. We all loved the original ending so we wanted to make sure that we weren't going to screw up our own movie. It was something we went into with open eyes, but also with a lot of care to make sure we crafted something that felt of a piece with the rest of the movie, but provided a little more closure and just that kind of burst that you want at the end so everyone walks out of the theatre on a high.

This interview has been edited and condensed.

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