39 Thoughts I Had While Rewatching ‘27 Dresses’


Spring is in the air (sort of, depending on where you live), and as more and more people receive their COVID-19 vaccines, it’s possible that nights out will soon be back on the horizon—which means, of course, the return of the Hungover Sunday Rom-Com Viewing Experience. This is a time-honored tradition that is best enjoyed with a bagel and iced coffee in hand, and the schmaltzier the rom-com, the better. To that end, today’s rom-com recap revisits the 2008 classic 27 Dresses. Let’s dive in, shall we?

  1. Will I ever be able to watch a wedding scene in a movie again and not think of it primarily as a potential super-spreader event?
  2. Katherine Heigl plays Jane, an always-the-bridesmaid-never-the-bride-type who we know is not living up to her full potential because she has brownish hair. Yuck!
  3. Question: How do you fit this many weddings (27, even!) into normal life? Does Jane have a job?
  4. Hey, Judy Greer!
  5. Jane sailing across the Manhattan Bridge in a cab is making me realize I haven’t been to Manhattan in forever. I should fix that.
  6. James Marsden plays Kevin, a wedding columnist (?) who is immediately spellbound by Jane, the Wedding Helper.
  7. Not to be a knee-jerk capitalist, but Jane should really be getting paid for her wedding doula work. Take a hint from J. Lo in The Wedding Planner, queen!
  8. Seriously, if I plan my friend’s entire wedding and all they do is thank me in a speech, I’ll be pissed. Where’s my floral arrangement, at least?
  9. Classic rom-com moment: Jane passes out and hits her head at one of a parade of weddings, and Kevin gets her back on her feet. They share a cab, she forgets her day planner, and he realizes she’s a wedding nut. Voila, we have a premise!
  10. Okay, yes, Jane does in fact have a full-time job. Interesting.
  11. Kevin pitches a front-page story about Jane, but his mean boss, played by Melora Hardin (Jan!), isn’t into it. He gets his way, but the stakes are high.
  12. Oh God, just to complete sad-girl bingo, Jane is in love with her boss, George. Judy Greer encourages her to go for it, as Judy Greer is wont to do, but Jane is too focused on picking up her baby sister, Tess (Malin Ackerman), from the airport.
  13. Tess is blonder than Jane, so clearly she’s happier, better-adjusted, and more popular.
  14. Man, only in a late-aughts rom-com is Katherine Heigl framed as the ugly duckling.
  15. Oh no! George falls for Tess! Scandal! Jane is clearly pissed, but suppressing it (not very well).
  16. Kevin correctly questions how Jane manages to pay for so many wedding gifts, and calls it “sad.” (Yep.) Then he asks her out, she says no, and he keeps trying, in that persistent way that’s cute in rom-coms and annoying-bordering-on-creepy in real life.
  17. Being the ultimate Nice Guy, George is a member of the Big Brother program, and Tess is very weird and racist to his “Little Brother,” Pedro. They all go to Pedro’s baseball game, and Tess pretends to be a vegetarian who hikes, because George is those things. Oy. The one thing I learned living in L.A.: Never pretend you like hiking to woo someone, because you’ll eventually be found out.
  18. Oh wow, Tess is even pretending to like dogs. The outrage!
  19. George proposes to Tess in a big, humiliating restaurant scene (or, I suppose, a “romantic” scene, if you like that sort of thing), and Jane is devastated, but literally plans the whole thing, because she’s a huge masochist and clearly does not have a therapist.
  20. Aw, man, it is actually kind of sad when Tess and Jane’s dad gives Tess their mom’s wedding dress, which Jane clearly wanted. Still, I’m unsympathetic. Speak up for yourself, Jane!
  21. Jane finally goes out with Kevin, and explains she can’t say no to her sister, so she’s helping to plan the wedding. He (and I) don’t buy it.
  22. Why are women in rom-coms always walking fast and talking in parks? Were there no bars or coffee shops in 2008? Did they predict COVID-19 socialization?
  23. Tess plans to recreate her and Jane’s parents’ wedding, which… is creepy?
  24. Another classic rom-com gal pal activity; Jane and Judy Greer do yoga. I don’t think you’re actually supposed to loudly discuss your personal life in a group yoga class, but I digress.
  25. Montage time! Jane tries on all five million of her bridesmaid’s dresses for Kevin, and it’s a fun scene, but I cannot get over the psycho Miss Havisham energy of devoting a whole closet in her New York apartment to old bridesmaid’s dresses. Yikes!
  26. “Twenty-seven dresses,” marvels Kevin. Hey, that’s the movie title!
  27. We’ve arrived at my twenty-seventh thought, which seems…on-theme. Unfortunately, it is “I have to pee.”
  28. Okay, I’m back. Kevin accuses Jane of wanting a big wedding and being Miss Helpful Wedding Girl to distract from her own desires, and we find out his wife left him for his college roommate. They’re both broken!
  29. Kevin realizes Jane is in love with George, she’s pissed about it and denies it, and then they…sing “Bennie and the Jets” at karaoke? It’s a pretty iconic scene, to be honest.
  30. God, I miss being inside of bars. And don’t even get me started on karaoke.
  31. Hookup time! It is a law of rom-coms that if two people are rain-drenched, they legally have to make out.
  32. Just as things are looking good for Kevin and Jane (Jevin? Kane?), she sees his front-page Styles story about her wedding addiction, slaps him, and storms off. Kevin is a real weenie to Melora Hardin, who correctly points out that he got a big story and should just thank her. Is she the real hero of the movie?
  33. Last straw time: Tess “forgives” Jane for shit-talking her in the story, then reveals she’s totally altered their mother’s wedding dress. Jane flips out. Fair enough.
  34. Wow, this is a bit of an overcorrection! Jane presents a whole slide show at the rehearsal dinner about what a non-vegetarian, non-hiking, non-chill party girl Tess is. Scorched earth.
  35. Okay, this is so mean. This is what I hate about passive-aggressive “martyr” types: All that bottled rage has to go somewhere! Tess and George call off the wedding, but Jane is still miserable.
  36. Kevin tells Jane, “I think you deserve more than what you settle for.” I don’t know if she does, personally, but to each his own.
  37. Tess and Jane eventually patch things up, and Jane cleans out her bridesmaid-dress closet. Symbolic!
  38. George and Jane finally smooch, but there are no sparks, because she’s totes in love with Kevin. She runs off to yet another wedding to tell him, and they kiss after a big public speech, thereby ruining some nice couple’s reception in the process like the selfish monsters they are.
  39. One year later, Jane and Kevin are getting married on the beach, with all of the various brides Jane has helped in the exact dresses they made her wear. Okay, thats kind of a good ending. Mazel!

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