I can’t stop watching Made Of Honor

Patrick Dempsey can juggle. That’s become an increasingly big part of his public persona over the years, and it’s also the reason I’ve seen Made Of Honor so many times. Whenever I come across this film on TV, I remember there’s a charming juggling scene so I stick around to watch that. And then I remember there’s a pretty good kiss in there somewhere and another scene or two I like, and before you know it, I’ve seen Made Of Honor a dozen times. It’s definitely not a good movie, and I’m not even sure it’s a movie I’m particularly fond of. But it’s a pitch-perfect example of the kind of easy watching comfort food that sustained the rom-com genre through its nadir in the late 2000s.

In fact, I stumbled across a deeply telling moment in a behind-the-scenes featurette about that aforementioned juggling scene, in which Dempsey’s male maid of honor tosses plates in the air as he explains that you can mix and match patterned dinnerware to find unexpected connections. As Dempsey and director Paul Weiland work out the staging, a production designer pauses to ask whether the plates Dempsey is holding actually do go together. Weiland replies, “I don’t think anyone’s going to really question it” to which Dempsey immediately agrees, “No one is gonna listen, really.” They’re not wrong, exactly, but it does speak to how both filmmakers and audiences mutually lowered the bar for romantic comedies in the late 2000s.

Made Of Honor is an interesting case study because it’s neither secretly good nor offensively bad (give or take some gay jokes, fat-shaming, and an uncomfortable runner about Bill Clinton and Monica Lewinsky). Dempsey stars as Tom Bailey, a proud playboy and wealthy inventor of the coffee sleeve. Tom thinks he has the best of both worlds because he gets to sleep around with hot women while spending his Sundays enjoying the companionship of his best friend Hannah (Michelle Monaghan). But when Hannah leaves for Scotland on a business trip, Tom realizes he actually has more than friendly feelings toward his bestie. Unfortunately, she comes back engaged to hunky Scottish royal Colin McMurray (future Grey’s Anatomy star Kevin McKidd). So when Hannah enlists Tom to be her maid of honor, he decides the best way to win her love is by sabotaging her wedding from within.

Made Of Honor was released as counterprogramming to Iron Man, and Entertainment Weekly’s Darren Franich convincingly argues that they’re secretly the same movie—only Iron Man challenges Tony Stark’s entitlement far more than Made Of Honor does with Tom’s. Made Of Honor is too busy pulling inspiration from other, better romantic comedies to spend much time worrying about things like comprehensible character arcs. (Tom’s biggest defining characteristic is that he can only say “I love you” to dogs.) Made Of Honor is a gender-flipped riff on My Best Friend’s Wedding mixed with When Harry Met Sally, a touch of The Wedding Singer in Tom and Hannah’s platonic wedding planning, and a little bit of You’ve Got Mail in Tom’s relationship with his equally philandering father (Sydney Pollack, in his final film role).

In fact, Made Of Honor often feels less like a real movie and more like a rom-com parody that would pop up in something like Tropic Thunder. A few years later, Paul Rudd and Amy Poehler’s They Came Together spoofed rom-com clichés with a basketball scene that was essentially lifted verbatim from Made Of Honor. Though it eventually grossed over $100 million worldwide, Made Of Honor is the sort of generically bland studio rom-com you forget about the minute you’ve seen it. Or, if you’re like me, it’s the kind of film you’ve practically got memorized because you find it to be such comforting background noise.

Because Made Of Honor has nothing new to add to the rom-com genre, it lives or dies based on how likable you find its leads—or, more specifically, how likable you find Dempsey, who’s very much its central focus. By 2008, Dempsey had already been on quite a rollercoaster ride with romantic comedies. He launched his career as a teen heartthrob in 1987’s Can’t Buy Me Love, was reduced to playing the guy who loses the girl in 2002’s Sweet Home Alabama, and then became a “McDreamy” pop culture sensation thanks to Grey’s Anatomy. After testing the rom-com waters again as a leading man in Enchanted, Made Of Honor was designed as his big star vehicle.

The film was shot in 26 days during Dempsey’s Grey’s hiatus, and he even got a say in its director. Dempsey settled on Weiland after seeing an early cut of his coming-of-age film Sixty-Six. As Weiland put it, “I think Patrick liked the idea of a Working Title director who could bring a slightly European sensibility. He didn’t want it to be a kind of in-your-face, bright, American romantic comedy.” Unfortunately for Dempsey, that plan didn’t work out so well. Still, he admirably commits to doing his signature debonair thing against the film’s broadly comedic background. Dempsey isn’t generally an actor with huge range, but he has a strong sense of what works for him.

As you can see in this cringe-worthy “Stars Of Tomorrow” production number from the infamous 1989 Rob Lowe/Snow White Oscars, Dempsey’s always had a palpable, almost desperate desire to be an old-school Hollywood leading man. It’s a quality that makes him either incredibly charming or incredibly grating, depending on your point of view. I fall into the charming camp, and the first act of Made Of Honor puts Dempsey’s easy charisma to great use in a When Harry Met Sally-style sequence where Tom and Hannah spend a Sunday wandering an idyllic food-filled New York City before attending his father’s latest wedding together. It’s the place where the film feels least like a bland studio rom-com and more like the low-key hangout movie Dempsey wanted it to be.

Dempsey and Monaghan generate some fantastic chemistry together, which is unsurprising given that having great chemistry with people is basically Monaghan’s thing. While she’s never risen to household name status herself, she’s been paired with an impressive collection of A-listers over the years. A non-exhaustive list of her leading men includes Tom Cruise in the Mission: Impossible franchise, Robert Downey Jr. in Kiss Kiss Bang Bang, Jake Gyllenhaal in Source Code, James Marsden in The Best Of Me, Mark Wahlberg in Patriots Day, Adam Sandler in Pixels, and Chris Evans in Playing It Cool. If she were a man, she’d almost certainly be playing a big screen superhero by now. Instead, she’s just on-screen romanced a bunch of actors who’ve played them.

Though Monaghan’s not the focus of Made Of Honor, she’s key to the film’s intermittent success. One of her greatest skills is projecting a “cool girl” sensibility while still maintaining a level of believable humanity to her characters. She manages not to embarrass herself in a sequence where Hannah tries on sexy wedding night lingerie for Tom, but she can also deliver real vulnerability when the film needs her to as well. Made Of Honor’s most innovative rom-com moment comes toward the end, in a scene where Tom and Hannah have a deeply intimate conversation from different sides of a closed door, which demonstrates both how connected they are and the fundamental emotional roadblock between them. It’s not much, but it’s at least more of an idea than the film lands on elsewhere, as it falls back on humiliating its supporting characters (including Busy Philipps and Chris Messina) and attempting a PG-13 version of Apatovian raunch.

Made Of Honor’s biggest mistake is not spending enough time with Tom and Hannah’s relationship in its second half, instead focusing on Tom’s far less engaging rivalry with Colin. (Highlights include Tom being forced into a “mini kilt” during a Highland games event where the crowd is inexplicably wearing Ren Faire attire.) Like a lot of rom-coms from the late 2000s, Made Of Honor prioritizes its heightened premise and slapstick pratfalls over the actual joys of watching beautiful people fall in love with each other. The improbability of Hannah’s whirlwind wedding and the cartoonishly broad jokes about Scotland undercut whatever emotional reality Made Of Honor initially had going for it.

Still, Dempsey and Monaghan are so consistently charming that I keep hoping Made Of Honor will somehow become the better film it could’ve been if it just featured the two of them hanging out (a.k.a. the How To Lose A Guy In 10 Days conundrum). By the time we’ve gotten to the door scene, the film’s almost over anyway, so I usually stick around to watch its lackluster climax. If a great movie is “three good scenes and no bad ones,” then maybe the key to making a bad rom-com halfway watchable is spacing out the good scenes so that you’re willing to sit through the terrible ones to get to them. Now that’s Made Of Honor’s real juggling act.

Next time: Two rom-com titans finally meet-cute in Notting Hill.