By Christopher Cappiello
From his chivalrous lawyer in “Enchanted” to the seemingly flawless McDreamy on “Grey’s Anatomy,” audiences are accustomed to seeing Patrick Dempsey as the nearly perfect guy – handsome, charming, thoughtful and committed. So when he bluntly informs his latest conquest early on in “Made of Honor,” opening May 2, that she won’t be seeing him tomorrow because he doesn’t “do back-to-backs,” we know we’re in for something a little different.
Dempsey plays Tom, a commitment-phobic entrepreneur with a lot of women, a lot of money and a best friend named Hannah (Michelle Monaghan), an art restorer at New York’s Metropolitan Museum of Art who is his opposite in every way. For 10 years since graduating college, this odd-couple duo have enjoyed Sundays together, hitting their favorite Manhattan cafe, strolling in the park and sharing news of their week.
When Hannah leaves for a six-week business trip to Scotland, however, her absence awakens long-denied feelings of attraction in Tom. When she returns, just as he is ready to tell her how he really feels, she shocks him by introducing her Scottish fiance, Colin (“Rome’s” Kevin McKidd), the “perfect guy” normally played by Dempsey. To make matters more awkward for Tom, Hannah also asks him to be her maid of honor.
“I wanted to do something old-fashioned,” Dempsey says about the classic romantic comedy structure of “Made of Honor,” “where it’s funny, but it’s rooted (in truth).”
The film’s energetic spontaneity is real, too. “We were constantly searching while we were shooting to make the scene funnier,” Dempsey says. “And Michelle was just so easy to work with and just ready to try anything – she was fearless in that.”
In an extended sequence where Tom is fully embracing his role as maid of honor in order to stealthily impress Hannah, he goes shopping for china patterns with her, expounding articulately on plate designs before ending by juggling a setting of precious china plates at a high-end store.
“I started off as a professional juggler,” Dempsey explains with the easy laugh that peppers his conversation. “I had my own show in high school and won second place in the international jugglers competition in ’82 or ’83. Paul (Weiland), the director, knew that, and he was like, ‘This scene’s not working. I was thinking, let’s have you juggle.’ And I said, ‘OK. Let me go find some plates that I can handle. And then let’s find a number of plates in case I drop any!'”
As Tom performs his various maid of honor tasks – from helping to pick out wedding night lingerie to stuffing the gift baskets for the luxurious shower he hosts – there is ample opportunity for jokes about his manhood. But when Hannah’s parish priest assumes Tom is gay, he just rolls with it, without making it a big deal. And while some of his buddies balk at helping with the baskets, Tom just assumes his duty without hang-ups.
“There was a fine line,” Dempsey says about the inevitable gay jokes associated with a male maid of honor. “How far do you push it? What is OK and what is distasteful? That is the thing we really wanted to make sure – that we could push it, but not be disrespectful. We tried all kinds of different things, and sometimes we were like, ‘Ah, we went too far.'”
In the days before the wedding, Tom competes with the burly Colin in traditional Scottish Highland Games, cavorting in the Scottish countryside in such outlandish activities as the “tree throw,” all the while dressed in a ridiculously small kilt.
“It was funny because at first I don’t think the locals, the Scots, realized it was a comedy,” Dempsey recalls, laughing. “So they were all laughing at me, making of fun of me and snickering. And it’s funny, because on (the) ‘Grey’s Anatomy’ (set), Friday is kilt day, so all the Scots wear kilts.”
In addition to Dempsey, Monaghan and Kidd, the “Made of Honor” cast boasts Oscar-winning director Sydney Pollack as Tom’s father, who we first meet as he is still negotiating a pre-nup in the back of the church before his seventh wedding.
Seeing the disastrous marital record of Tom’s father gives Tom’s issues with commitment a deeper meaning. “You can’t just say, ‘Well, he’s a guy. It’s male energy gone crazy,'” Dempsey says. “It’s got to come from something true. And you see it with the father. … We need to see that and have it be fun.”
Pollack’s presence added a lot to the film, on and off camera. “We had a really classy movie once (Sydney) came on board,” Dempsey says. “To work on those scenes with him, I couldn’t believe it. … He gives it so much weight, but at the same time keeps it entertaining. I was thrilled when we got him.”
While they never worked together on the show, Pollack and Dempsey share memorable credits on “Will & Grace,” with Dempsey’s turn as Will’s closeted sportscaster boyfriend providing an important turning point in his career.
“It really changed my career profoundly, I think,” he says with appreciation. “By doing that, people discovered me in a whole different light. And that was the beginning of a big turn.”
So what does the handsome, likable star with the impossibly thick head of hair think of his big gay following? “Oh, it’s great,” he says, with another big laugh. “I think the important thing is everybody just needs to be true to themselves. And I think that’s the key. Who are you? Embrace that and be open with that and not hide it. And I think people live a much better life when they can do that, (even though) sometimes it’s very hard to get to that place.”
Advice his character could have used in order to avoid a long, embarrassing, but delightfully hilarious journey in “Made of Honor.”