When it comes to rom-coms, I’d say I’m a happy medium. Sure, I’ll cry at The Notebook like any self-respecting millennial, but come movie night, I’m just as likely to choose a murder-y thriller over something with a meet-cute and a montage set to everyone’s favorite pop song from three years ago.
And yet… I have a soft spot for the 2008 romantic comedy 27 Dresses, starring Katherine Heigl as the consummate bridesmaid Jane and James Marsden as Kevin, the ultra cynical wedding reporter who secretly writes about her. The plot? Jane has been a bridesmaid 27 times (yes, she keeps the dresses), is secretly in love with her boss George (Edward Burns) and gets swept up in a whirlwind of wedding-related chaos when her younger sister Tess (Malin Akerman) swoops in to marry said boss.
No, it’s not exactly a Nora Ephron classic, and yes, it has a 40 percent score on Rotten Tomatoes. But there’s something comforting about it. Like the cinematic equivalent of ordering mozzarella sticks at a fancy restaurant: objectively bad, yet deeply satisfying.
So I rewatched it to figure out what exactly keeps pulling me back to this decidedly mid-tier rom-com. My 27 thoughts about the film, in chronological order, below.
- How is Katherine Heigl supposed to be the underdog in this movie? She’s gorgeous, emotionally available and funny as hell. She’s a catch.
- Getting your friend to stand in for you at your wedding dress fitting is completely unhinged behavior. I don’t care how busy you are or the fact that you’re the same size, that’s crazy!
- These purple bridesmaids dresses look like they were cut out of construction paper. Everything is so…angular. Jane needs new friends.
- Why does Judy Greer always play the bestie? She has lead-role energy.
- James Marsden is so smug. And so cute. And so obviously the guy she’s going to fall for. (Oh, also I should really rewatch Jury Duty. Marsden playing himself is too good.)
- Maybe one of the reasons I love this movie is because of the ‘00s energy. The flip phone! The macarena! If this movie were made now, would Jane really have hailed a yellow cab for the night or would she just have Venmoed someone $300 and trauma-dumped in the UberPool?
- Going across the Brooklyn Bridge on a Saturday night for two weddings? What a nightmare. Jane is a very good friend. And a serious people pleaser. And definitely the oldest child.
- As someone who has worn a wedding dress and been a bridesmaid myself multiple times (though nowhere near 27), I can attest that the bride does not need a friend to help her pee. It’s becoming abundantly clear that Jane needs better boundaries and better friends.
- Oof, Jane being desperate to catch the bouquet so she can finally be happy is so problematic. But let’s move on.
- Jane’s planner is a mess. This woman needs a digital calendar (and a therapist).
- The real fantasy here isn’t the romance—it’s the Manhattan apartment with closet space for 27 bridesmaid dresses!
- The bosses in this movie are a lot. Kevin’s editor gives serious girlboss energy but I’m not sure her threats are HR-approved (“Alright, one chance. And if I don’t like it, you go back to commitments for the rest of your life with a big smile on that ridiculously handsome face of yours!”) Meanwhile, George leaves his dry cleaning on Jane’s desk? Toxic.
- Jane may be a Type A, people-pleaser but dropping the F-bomb at a 50th wedding anniversary party is objectively funny.
- That apartment though. Jane is a glorified assistant and somehow has giant closets, a separate dining area and natural light? Make it make sense.
- The sister drama is so real.
- Yikes, Kevin writing in Jane’s planner is kind of a red flag. It’s so intrusive!
- The twist: Kevin is actually Malcolm Doyle, Jane’s favorite wedding columnist. (“I feel like I just found out my favorite love song was written about a sandwich” is a great quote.)
- OK, I take back what I said about rom-com montages. The montage of all 27 dresses is probably my favorite scene of the film. And wait, do people actually have themed weddings like “Gone with the Wind”? If so, please invite me.
- The way Jane lies to protect her sister isn’t endearing. It’s enabling.
- “You’d rather focus on other people’s Kodak moments than make your own” is a killer line.
- Actually, the “Bennie and the Jets” singalong is my favorite scene. It’s fun, it’s flirty, it’s rom-com perfection.
- Nooooo, Kevin’s article about Jane, aka the forever a bridesmaid and never a bride, hits the stands. Hold up, can a newspaper actually publish a feature like this on someone without their permission? This feels like a defamation suit waiting to happen. Lawyers, weigh in.
- The real betrayal? Tess cutting up their mom’s wedding dress. I gasped then and I gasped now.
- Jane’s takedown of Tess at the rehearsal dinner may be deserved but I still cringed. It was so… messy. But Kevin’s response? “I saw what you did in there and I thought it was amazing. Was it absolutely certifiably nuts? Yes it was. But you did something Jane. For the first time you were not just the perfect bridesmaid!” Swoon.
- George comes across as Mr. Nice Guy but calling on Jane to be his last minute date after he’s called off his wedding to Tess is bizarre. Thank goodness there was no chemistry in that kiss!
- Yes, Jane! Be the main character in your own life! Jump onto that boat! Get the guy! And the look that Kevin gives her is so dreamy.
- I can’t decide if making all 27 former brides wear the bridesmaids dresses at her own wedding is sweet or petty. Either way, I love it.
Honestly, the slow pan to Kevin at the end as Jane walks down the aisle still gets me. 27 Dresses may not go down as one of the greatest rom-coms of all time but there’s something about its chaotic charm and comedic sweetness that makes it so rewatchable. 27/10 would recommend.
