In 2005, Michelle Monaghan grabbed our attention when she co-starred with Robert Downey Jr. (Iron Man) and Val Kilmer in Kiss Kiss, Bang Bang and the vivacious actress continues to impress audiences with her diversity and incredible performances. In the last few years we’ve seen her share the big screen with some of Hollywood’s top leading men and now she co-stars with yet another great actor, Patrick Dempsey (Enchanted, “Grey’s Anatomy”). The two paired up for Columbia Pictures’ new romantic comedy Made of Honor, in which Dempsey’s character is quite the player and doesn’t realize he has feelings for his best friend Hannah (Monaghan) until she meets someone else.
CS: Did you look at any other romantic comedies or do you have any favorite classic romantic comedies?
Patrick Dempsey: I didn’t look at any contemporary movies. I looked at a lot of older movies, Cary Grant, that period, screwball comedies of that era I think were what we were trying to do and also the tone was a working title of “Four Weddings and a Funeral,” something like that, so that was what we were trying to do with it. It’s hard because this is a genre that’s been played out so much. You can’t reinvent the wheel, but you just hopefully want to make it entertaining and that people go along for the ride. And we kept inventing and working on the script throughout. I mean, every day was something that we had to kind of go in and go, “Okay, how do we make this fun? How do we find the joke in the scene?” And the other thing that we were really thinking a lot about was “How do we make this visually stimulating?” So that it’s lush and pretty. I think we had a wonderful DP who did a great job with the look.
Michelle Monaghan: I think also what makes it unique from a lot of romantic comedies is that it’s kind of a romantic comedy for guys, it’s told from the male…
Dempsey: The male point of view.
Monaghan: A male point of view. Usually the girl doesn’t get the guy, the girl has a broken heart, the girl goes to the girlfriends and they help mend the broken heart, so I thought it was really refreshing, this take on it. My husband went to see it and he absolutely loved it and I got really excited, because typically guys always refer to romantic comedies as chick flicks and I’m excited because I think guys will get taken to this by their girlfriends, but I think they’re going to walk out of the theater really entertained. Patrick has a unique ability to connect with male guys, as well as women for obvious reasons, but, you know, I think he really appeals to guys as well. So that’s what sort of attracted me to the script.
CS: What’s the trick of playing your characters ten or fifteen years younger?
Dempsey: It was hard to go back.
Monaghan: Yeah, I hate that part.
Dempsey: I do, too. That was really hard. We both hated it.
Monaghan: I didn’t want to go back. We wanted to do something else. Yeah, we didn’t like it at all actually.
Dempsey: I had no desire to go back to that period of my life.
Monaghan: I was so annoyed with myself, I was just like, you’re just such a whiny little I didn’t like it at all. I think it’s probably much easier to play older.
Monaghan: Than it is to play younger.
Dempsey: I would rather look forward down the road, than look back.
Monaghan: Yeah, I do too. Neither that’s funny…
Dempsey: We did not like that. [Director] Paul [Weiland’s] like, “It’s going to be fine.”
Monaghan: And still when I see it, I kind of cringe.
Dempsey: Yeah, me too. I can’t watch that part. I close my eyes. I just flash back to everything in my youth.
Monaghan: Yeah. Yeah.
Dempsey: So thanks for bringing that question up.
CS: Why are people so often slow in realizing they have something great right there?
Dempsey: Oh, because they don’t see it, it’s right there in front of them, they take it for granted, I think. And it’s not until it’s gone that you realize how special it is.
CS: Do you think it’s a fear of commitment, as well?
Dempsey: Well, in his particular case, certainly. And I think it’s because of the dynamic, the other thing we were working on, is like, how do we keep these people apart? Because obviously why wouldn’t they have an affair earlier? But then we wouldn’t have a movie. So we had to stop that kind of questioning, because you just wouldn’t have a movie. But we were like, what’s the deeper issue here? And I think the thing we worked really hard on developing was the relationship with the father. And you see the dynamic with the father really affects him and why he doesn’t believe in marriage because he has not seen one that’s healthy, from his father. So I think that was one of the reasons why he didn’t do it. And also because he was fulfilled on a friendship level and had his physicality, and the sexual and that kind of thing in other relationships.
Monaghan: He had his cake and ate it too.
Dempsey: Yeah. He was eating a lot of cake. But he just didn’t have the depth and the emotion that he has.
CS: Patrick, your character is kind of this player and he has all these rules, but he’s very honest and upfront about it, which I thought was so funny.
Dempsey: We did several passes, it was very harsh early on in those first drafts. We were like, this guy’s completely unredeemable, there’s something about it. And it was an actual rule that someone, one of the writers had. And we were like, let’s use that, it’s perfect. Because he is upfront about it, at least they know where they stand. He’s not manipulating. He’s like, “Here it is. If you want to do this, great. If you don’t, that’s fine, too.” And he’s nice. He’s just very clear in what he likes and what he doesn’t like.
CS: And he won’t break the rules.
Dempsey: He won’t, no.
CS: Do you see a parallel between him and your character on “Grey’s Anatomy?”
Dempsey: I would never do that. I like the fact that he was very honest about it. That he’s a bit of a player, which I couldn’t emotionally handle that. I don’t think. I know I couldn’t do that.
CS: Even in your younger days?
Dempsey: I think, just, it’s kind of empty after a while. I couldn’t do it.
Monaghan: It seems like it would be stressful.
Dempsey: I would be stressed out, yeah. But he’s clear about it, so he’s fine. I don’t know how he does it, but he did.
CS: You have some great physical gags. The restaurant scene with…
Dempsey: That came about right at the last minute. Paul said, “What can we do here? Is there anything physical that we can do? We watched a lot of playback, which was really fun. And everybody had input. We’d watch it and go “Okay, that works, that doesn’t work, let’s try to change it.”
Monaghan: That was really fun that day, that was really great. It all just sort of came up and the gag worked so good. And every time it happened, we really laughed. We did a lot of fun things that day, as far as that scene.
Dempsey: That scene, we tried a lot of different things. Paul would, after each take, we would try something different, and try to get it as realized as possible, because it wasn’t quite there on the page the script wasn’t right there all the time. And we were constantly working on it.
CS: That’s interesting because you were talking earlier about the whole idea of doing a romantic comedy and I see it as a very fragile thing, because it can so easily seem unreal. You’re looking for these touchstones that people can identify with.
Dempsey: You have to have the heart of it, I think. The thing was we didn’t want to be broad. We need to have moments where that would happen, like tiny shorts guy and some of the slapstick and those moment, the beads, I should say. Those are broad moments, but we didn’t want to do there’s a lot of comedies out there right now that are very hardcore, you know, much more aggressive than this one. We wanted to keep it so there was a nice heart to it, a simplicity to it in the performances, and there was more of a chemistry and a camaraderie. And you’re right, it’s fragile, because you have to find that balance and to find the humor in it at the same time. And that’s what we were constantly working on. And we would try things this tonally different each take, which is what it was fun, it was a lot of work, because you never felt like you got it. And at the end of the day, you had more options in the editing room, so that was the key.
CS: You have this great scene with Kelly Carlson as your drunken stepmother.
CS: Did you do a couple of takes on that and how did that go down?
Dempsey: That went very quickly. And I couldn’t believe the day. That was one of my, I think one of the days I enjoyed the most. It was just really playful and really easy. And it was early on in the shoot, I think it was day number two or something like and Sydney was there, too, something like that, so it’s like, wow, he’s over there, she’s great, all you have to do is react off of her.
Monaghan: I got to kick him, so.
Dempsey: It was just a lot of fun. It was playful and easy.
CS: In the film, Sydney Pollack had that great line about when you love someone you let them free and calling that bulls**t. You go after them. What’s your take on that?
Dempsey: I think you should follow your heart and everything. I think when you feel strongly about something you should follow that. You try to instill that in your children and yourself. It’s like what is it that’s passionate. What’s your passion? What do you really want to go after because that’s the goal and that’s what you need to try to always remember.
CS: How excited were you to have Sydney Pollack as your father in the movie?
Dempsey: Oh it was huge. I thought once we got him, the movie was made in a lot of respects. After that and then you [Michelle] came I thought, “Oh great. We’re good. We have great chemistry, fun spirit.” We needed something that was really solid after the father so that when you saw him it was a great character. You were like, “Oh we love this guy.” Once we got him, the whole fit just got really rich.
CS: Did you try to avoid being a fan while working with him?
Dempsey: I was so nervous the first time I sat down with him. I had so many questions I wanted to ask him. I was like, “Should I? I know what it’s like to be on the other side of the table. Oh what the hell. I’m going to ask him anyway.” He was really gracious about it and wonderful and very supportive. We talked about a lot of different things. Once you got comfortable, you realized he’s just a nice guy and it was easier to talk about. For Paul he was very nervous about it.
Monaghan: Paul was very nervous.
Dempsey: He would go, “Can you tell him?” I’d go, “I’m not going to tell him.”
Monaghan: It was sweet. He was like, “How do you direct Sydney Pollack?”
CS: I found so many parallels with “Harry Met Sally.”
Dempsey: With the flashback?
CS: Well, not just with the flashback, but the sense of a relationship and the idea “Can a man and a woman be friends?” And not be romantically involved. And I wonder how you approach that? The idea of creating the Hannah the relationship that they had because, as they said in “Harry Met Sally,” there’s that sex thing that comes up, even with your best friends. You never have that out of your mind.
Monaghan: I think it’s, how much do you value a relationship? I mean, I think that is the age old question, “Can you have sex with your best friend and still be best friends?” I have a best friend who is a guy and we haven’t had sex, so you know.
Dempsey: But does he want to?
Monaghan: No! I don’t think, I don’t think so, no, he was my maid of honor actually. He was my maid of honor. So that works. I can attest to that. But I think it’s a matter of, if you’ve got a great relationship and you can be honest with each other and say, you know, let’s give it a shot, let’s take it to the next level, if it doesn’t work out, you know, I hope you’re really, really good friends because that could be really, really awkward, you know? And if it does work out, then that’s just like the best scenario ever. I mean, what could be better than marrying your best friend or falling in love with your best friend, so I think it’s an individual case for each couple.
CS: Did you make him go through the same sort of rigmarole?
Monaghan: No, absolutely not. I just made sure he could make a stiff cocktail.
CS: Was the juggling in the script?
Monaghan: No, he did that.
Dempsey: No, Paul came up [to me]. We were like, “We’ve said this in all of these scenes. How do we move the exposition? He’s like can you juggle? Go juggle these plates?”
Monaghan: He did it. I turned around and he was juggling these plates.
Dempsey: I hadn’t juggled in awhile and that’s something that came up that morning.
CS: So you have juggled before?
Dempsey: Oh yeah, I was second in the international juggler’s competition in ’83 in the junior division. I wanted to join the circus. That was my first thing and I had my own show.
CS: Why didn’t you join the circus?
Dempsey: I was too young. They wouldn’t let me in.
CS: Your own show? Where did you perform at that age?
Dempsey: In Maine. I did juggling, slapstick comedy, unicycling and magic. That’s what I did in high school. That was my job.
Monaghan: He’s too much. I can’t take it.
CS: Was that a good training ground for you?
Dempsey: Yeah, Cary Grant started off as an acrobat and we talked about that and what we liked about those movies and Paul was like, “What’s your background?” and I told him and he’s like, “Oh that is good to know” and then he just sort of let it go. Then he would just start pulling that stuff out as he went along.
CS: Michelle, Patrick’s character sleeps with almost everyone you know and she sees how disconnected he is from women so why do you think she still falls for him?
Monaghan: Because I think he’s probably pretty good in the sack. I’d be crazy not to find out.
Dempsey: (Laughing) She has the best sense of humor. The characters, the characters. We’re in trouble now.
Monaghan: She really does have feelings for him and she’s had feelings for a long time. She knows that he’s not ready to commit, but they certainly have a connection and they’re best friends because they can laugh at each other, they’re honest with each other and I think if you have that foundation then no matter what you’re always going to feel connected. I think that when she starts to realize that he’s now coming around, I think it’s that poignant moment, it’s before the taking out and your helping me with my vows and I think I realize in that, there’s a slight moment where my character realizes that he’s maybe talking about me. Then the kiss gets her as well. What would you go with, somebody who you just met on a whim ultimately and made a really hasty decision or somebody that you have a real history with? Obviously you go with the one you have a history with.
CS: You’ve set the standard for working with the hottest men. Where do you go now?
Dempsey: There’s no where to go now. This is it.
Monaghan: Exactly. I’ve plateaued. Maybe I’ll be lucky enough to do a sequel with him. I don’t know.
Made of Honor opens in theaters on May 2.