Trying To Rewatch 27 Dresses, This Time Without The Cynicism

Let us time travel from 1991 (and our last film, Father of the Bride) to 2008, for a movie not about a wedding-impaired dad but a female wedding guest — a frequent, nearly professional, possibly pathological bridesmaid, no less. Yes, I’m talking about 27 Dresses, the rom-com about being in way too many weddings (seriously, this cannot be financially and emotionally healthy) that helped make Katherine Heigl a household name.

I have to be honest with you. I did not like this movie the first time I saw it. I found it belittling to women (though, interestingly, it’s written and directed by women); belittling to brides and grooms and sustaining love and the real hardships of relationships; belittling to weddings in general; and, perhaps most heinously, belittling to the people watching the film. Maybe you feel differently (if so, please, tell me why you like it). My feelings are intensified by the fact that the movie shares a similar kind of structure with that of my book — Jane goes to wedding after wedding, I go to wedding after wedding — and people frequently ask, when I tell the premise of Save the Date, “Oh, like 27 Dresses?” I assure you, they are different.

I had to get over all that, or at least try to, and so I cleared my mind of bias like any good repeat movie-watcher should do, I turned on my TV, and I watched 27 Dresses for the second time.

So, how does it measure up? Click through to rewatch 27 Dresses with us.

Plot Summary: Jane (Katherine Heigl), a woman in her twenties (we never know her exact age but late twenties seems about right), has been in love with weddings ever since realizing as an 8-year-old that making sure the bride has a perfect day is “her purpose in life.” She’s served as a bridesmaid in 27 weddings, keeping each of the dresses as mementos in the closet of her inexplicably giant New York apartment. Alas, this bridesmaid-who-loves-weddings has never been a bride, partly because she harbors a deep crush on her boss, George (she's remained his assistant over the years, ignoring whatever ambitions she might have to keep close to him). When Jane’s sister Tess (a model, obviously) comes to visit, she quickly steals George, the two announcing their own wedding within weeks. What’s to be done? Enter Kevin, played by James Marsden, the wedding reporter who disdains weddings and the whole associated industrial complex, and wants to write about Jane, the perpetual bridesmaid, mostly so he can get promoted out of the “taffeta ghetto.” Antics. Ensue.

The Happy Couple: There are quite a few couples in this movie, but the ones we need to pay attention to are Tess and George, who fall for each other partly because Tess is pretending to be someone else — more specifically, the woman she thinks George wants (a vegetarian, an animal lover, sporty, etc.). Then there’s our countering twosome, Jane and Kevin, the odd couple who, in typical rom-com fashion, think they can’t stand one another until they get drunk, bond over a commonality (they both like to look at the groom’s face as the bride walks down the aisle!), fall briefly in love, and hook up — only to realize upon light of day that, really, they HATE each other. Or, do they? We all know they’ll end up together in the end.

Wedding Logistics: Speed-wedding-planning Tess and George (assisted by Jane) want to have their wedding at the Central Park Boathouse, where Jane dreamed of having her wedding. Fortunately, there’s a cancellation. Tess wants to wear their deceased mom’s wedding dress, which Jane had wanted to do. Tess cuts the dress up into pieces and uses a small part of it, ensuring the dress cannot be worn again by Jane.

Aside: Tess is awful in this movie, a thoughtless bridezilla caricature, to the extent that it’s hard to believe Jane or anyone else would have much to do with her at all. (She forces the child George mentors to clean her apartment!) But, Jane is equally caricatured, a woman who has no idea what she wants or what she can be, aside from her role as the perfect bridesmaid.

Back to the logistics. There’s not a lot of talk of how much things cost or of how Jane can afford bridesmaid duty at so many weddings on her assistant salary. In terms of all the organizational logistics, Jane has them covered by way of her datebook, which Kevin steals and uses as research and a way into her life.

Wedding “Disaster:” In the beginning of the film, at one of the two weddings Jane alternates between in one night, there is a bouquet toss in which she jumps for the bouquet and is knocked out by another (painfully) eager guest. This is her meet cute with Kevin, and it says a lot about this movie that their romance begins in unconsciousness. The other main disasters are Kevin’s article about Jane (and Tess), which comes out after he’s kinda sorta fallen for Jane and threatens to destroy all. And, then, of course, there’s the scene when Jane, finally infuriated to action after her mom’s wedding dress is destroyed, reveals at Tess and George’s rehearsal dinner that Tess is not what she seems. Later, after George breaks off that wedding, he and Jane kiss, and she feels nothing, which, in rom-com language, means he’s not for her after all. There are no hard feelings. It’s time to chase down Kevin on a boat!

Film’s Ability to Transcend Time: The biggest timeliness issue I see with this film (aside from the really trope-y “goth wedding” in it) is that viewers are more sophisticated about weddings than the characters are. I think there’s an evolved or at least evolving sense of what people want in a wedding today, and I hope there is also a greater respect for bridesmaids — that they needn’t give up everything to attend to a bride — than is seen here. At one point, Jane says, “The perfect bridesmaid always does what she’s asked,” and that really makes me cringe.

Maybe 27 Dresses is perfectly fine as light fare in the background on a lazy Saturday, but the core of it — the idea that most of all women desperately want to be married and better do what they’re asked of brides lest they foul up their own chances — is a problem for me. Oh, also, Jane would never use a datebook if this movie were made in 2014. She’d keep track of her duties via a cloud-based program.

Mistakes: Jane picks up Tess at the airport. Who picks anyone up at the airport in New York City? Also, as mentioned earlier, the size of her apartment is ludicrous (and I want to live there).

Attention to the Wedding Guests: This movie is all about the wedding guest, or at least, all about one of them. Of course, in the end, she’s also the bride, and therein, again, is the problem. Guests don’t always want to be the bride, nor do we need to see them only as early iterations of such; they bring plenty of other feelings and thoughts and concerns to each event they attend.

Cheesiness Level: High. In the end, after the revealing kiss with George, when Jane confronts Kevin at a wedding he’s covering on a boat (she scales a closing bridge to get there), she gets up on stage, taking the mic from the bride, and tells him, “Fighting with you is the best thing that’s ever happened to me.” He stares at her like he’s got something stuck in his eye and growls, “Get over here,” and she does, and they kiss. The next thing you know, it’s a year later and they’re on the beach getting M-A-R-R-I-E-D.

Surprises: Judy Greer is great as Casey, Jane’s “I love you but get yourself together!” BFF. I would prefer the movie in which Judy Greer is the recurrent bridesmaid, however, because she would not take the crap Jane puts up with. Also, Melora Hardin is fun as Kevin’s tough boss. The other surprise with regard to this movie is the apparent belief that a bunch of drunk people at a dive bar would happily rock out in unison to “Bennie and the Jets.”

Anxiety Production: Oh my god, this movie stressed me out from the very beginning, when we learn from Jane that you can be in two weddings in one night in New York City so long as you pay a cab driver to transport you back and forth throughout the night and change your clothes in the cab each time, and dock him the money you’ve promised him when he ogles you. Also, the consistency with which Jane keeps her true feelings and emotions to herself gives me hives.

Similarity to Going to an Actual Wedding: The movie evoked a range of emotions in me, from argh to blargh to a laugh and smile — hey, I like the montage in which she tries on all the dresses — to, in the very end, a few actual tears. But, most of the weddings I’ve been to have been more entertaining, and the couplings involved have made me significantly happier than I felt watching this. I guess, the truth is, I’m just not all that invested in Jane and Kevin (nor Tess and George), and being invested in the couple and really caring about them is what makes or breaks a wedding.

Tears: I am a sap, and when the screen pans to all those women for whom Jane was a bridesmaid now being her bridesmaids (and wearing those wackadoo bridesmaid dresses she wore for them) at her own wedding, I got a little weepy. Yes, it’s a corny scene, but the element of interwoven friendships with regard to the weddings we go to gets me every time. And, I am happy that Jane gets what she always wanted in the end. I am not a soulless monster.

Overall: D+. I’m sorry. I haven’t really changed my mind. I still don’t like this movie. But, I do like the bridesmaid-dress montage!