30 Questions I Still Have After Re-Watching ‘The Holiday’

Thursday marked the 10th anniversary of the release of one of the modern classic holiday movies of our generation: The Holiday.

Even those of us who would like to pretend that we aren’t into Nancy Meyer’s aptly-named depiction of two transatlantic, house-swapping single women can’t help but fall prey to the unabashed HGTV-level house porn, the contempo-casual soundtrack, and the undeniably heartwarming dialogue. It is the movie equivalent of a cashmere sweater that isn’t really in style anymore, but feels too damn cozy to resist.

That said, I still have some very persistent questions about this movie, particularly after my 10-anniversary viewing of the film last night (I had several glasses of wine, so please bear with my questions, here):

1. Okay, first and foremost, does “home exchange” even work like this?

Kate Winslet and Cameron Diaz meet online, exchange names and the bare minimum of basic information, and are promptly like “Dude, do you want to live at my house starting tomorrow??” Are you honestly telling me it’s this easy to screen a total stranger for staying in your house? And what about the financials? What if Cameron Diaz turned out to have a penchant for raucous orgies and Kate Winslet came home to a wrecked cottage full of wine stains and used condoms? I’m just saying, the whole thing seems like a legal issue waiting to happen.

2. What the hell was that fake movie clip at the beginning?

Two people in period garb run up and start making out with one another for a good two minutes with absolutely zero dialogue. I want to watch whatever movie that was and throw popcorn at the screen.

3. Is it standard to smoke indoors in England?

Okay, I actually do have the answer to this: a smoking ban was introduced in England in 2007, and The Holiday was released in 2006. I KNOW YOU WERE VERY CONCERNED ABOUT THIS, YOU’RE WELCOME.

4. But really, how does a single journalist afford an entire cottage?

I should really stop questioning the real estate situations in romantic-comedies, as they are always infuriating. But seriously — an adorable little cottage with amazing finishes and a clawfoot tub? I’m not buying it, Kate! Pun intended!

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5. Sh*t, how did I forget that scene where Kate Winslet tries to kill herself??

Somehow I managed to edit out the part where Kate leans over her stove and starts bleakly inhaling noxious fumes before the *ping* of Cameron Diaz’s message convinces her that life is still worth living. Like, damn, Nancy Meyers — way to introduce this horribly dark plot twist and then say “GOTCHA, NO SUICIDE IN THIS MOVIE, MOVING ON.”

6. Who do these ex-boyfriends think they’re kidding?

This is a huge discussion that probably requires its own post, but Kate Winslet and Cameron Diaz’s respective former lovers are both such despicable human beings it’s almost comical. They both cheat on their girlfriends, then somehow convince both of them that they brought the infidelity upon themselves. Kate Winslet’s former beau, Jasper, is so manipulative that he literally flies across the world to put her back under his thumb, with zero intentions of leaving his fiancé. He then has the nerve to basically say, “Ugh, Kate Winslet, why can’t you just let me live and stop harshing my womanizing mellow?” And yes, I understand that the movie wants me to feel all of these things — but I just need you guys to understand how deeply it frustrates me that these kinds of humans exist, okay?

7. Is “Movie Trailer Maker” an actual job title?

This sounds like a fake job title you give yourself to sound more impressive on first dates because “YouTube Enthusiast” just doesn’t have an impressive ring to it.

8. Does anyone realize the Cameron Diaz’s ex talks exactly like Donald Trump?

Perhaps I’m just traumatized, but it really is uncanny. The accent, the hand gestures — it’s spooky, man.

9. Am I supposed to care that Cameron Diaz can’t cry?

While I understand that a traumatic backstory is necessary for character depth, I feel deeply uncomfortable every time Cameron Diaz “tries” to make herself cry onscreen and it’s supposed to act as a funny metaphor for her cold, bitter heart or something. I’m sorry, I don’t care! Hooray, Cameron finally found a man who makes her cry! Some people would venture to say that’s actually a bad message to perpetuate, but SHUTUP, SYMBOLISM.


10. Why aren’t Katherine Hahn and John Krasinski in more of this movie??

I’m sorry, I just love them and want them around all the time.

11. How is it possible that the LiLo/Franco movie is the most hilarious part of this film?

The fake movie trailer for Deception, starring Lindsay Lohan and James Franco is so funny, I think it might trump any other meta joke in this movie. You could post that trailer to Facebook, give me amnesia, and I would probably believe it was 100% real. You just can’t beat this exchange:

“How do you happen to have two guns?”

“I didn’t think one would be enough!”

Still gets me every time.

12. Why can’t Cameron Diaz’s driver turn around??

I’m just saying, it’s a bold move to have a driver who says “Sorry, I’m done driving.” I mean, I get it: it’s funny to watch Cameron Diaz attempt to traverse snow in stilettos. But like, come on, dude. Do your job.

13. Is there actually a magical place where you can drink from an open wine bottle in the store?

If so, I want to go to there.

14. Why did Kate Winslet leave her adorable dog behind with a total stranger?

I’m just concerned for Charlie’s well-being. He’s one of my favorite characters, and I think he deserved more consideration, especially since I have no idea if Cameron Diaz will remember to feed him while she’s busy “finding herself.”


15. Hey guys, remember The Killers? 

2006 was a time, right?

16. Jack Black, who grabs an eyelash like that?

I dunno, This seems like a super-wonky eyelash-fetching position. If someone did this to me, I’d be like “No, we are definitely not going on a date in England.”

17. Does Cameron Diaz not know better than to open her door to handsome strangers??

A dashing Jude Law shows up in the middle of the night, banging on the door, demanding to be let in, and Cameron Diaz is just like “Oh sure, and also can I get you a drink?” Like, I’m glad everything worked out, safety-wise, but this is legitimately how people get murdered, Cameron.


18. Also, hey guys, remember Jet?

2006 was an especially good year to be a group of white dudes! Oh, and also this year, I guess.

19. Why are there any other relationships in this movie apart from Kate Winslet and Eli Wallach? 

This is, without a doubt, the most charming pairing in this entire movie, and the one that warms even the coldest, most callous heart. Not only does it hold a certain multi-generational Harold and Maude-esque appeal, but it manages to turn film history and the Golden Age of Cinema into an analogy for modern love. Sure, the whole plot might be a shameless grab for my heartstrings, but I don’t care — because at least it bothers to be creative about it.

20. What was the last good movie Jack Black was in?

There is a correct answer, and that answer is Bernie. Also, someone please hire Jack Black for more interesting movies, please.

21. Is anyone else concerned that Cameron Diaz is hearing movie trailers in her head? 

What if the entirety of The Holiday was just a movie idea unfolding in Cameron Diaz’s character’s head?? And then she wakes up from her dream and is like, “I’m done making trailers, cast me as the lead in this movie I just wrote”? What an incredible twist!

22. Who made that amazing goddamn tent fort??

I don’t care how impish and precocious these tiny British children are, they didn’t make this damn tent. A pillow fort architect make this magical freaking tent.

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23. Does Kate Winslet ever call Jude Law back and tell him to stop f*cking women in her bed? 

I mean, as a considerate older brother, it seems like refraining from intercourse in his sister’s bed is the least he could do. Also, I just feel like I was robbed of a scene where Kate Winslet actually gets to yell at Jude Law for having sex with her house-sitter, because I think that would be cathartic for women everywhere.

24. The “best drink in town” is Starbucks?

Jack Black brings Kate Winslet “the best drink in town,” which is clearly a Starbucks frappuccino. And while I will concede that it’s probably pretty accurate for Los Angeles, it just seems like sort of BLATANT PRODUCT PLACEMENT to me.

25. Guys, remember Blockbusters?

Ah, yes. This movie was definitely a peak moment for Blockbuster stores. If more movies featured Jack Black yell-singing in Blockbusters, they would probably still be in business.


26. Is that the best allotted “f*ck” in a PG-13 movie? 

Every PG-13 film is allowed to have one “f*ck” and maintain their rating. The moment when Jack Black listens to Kate Winslet’s long, emotional monologue before saying “Well, fuck. You need this more than I do,” and handing her a drink is definitely one of the best. (Though several people might assert that the one in Anchorman is better, to which I say “Calm down, nobody actually cares.”)

27. Does there need to be sexual tension between Kate Winslet and Jack Black?

I appreciate that their romantic relationship is hinted at more than explicitly explored, as it seems to honor them more as fully-developed characters — but like, does it even need to exist? Could they not merely be friends who help one another through difficult relationships hiccups? Does Kate Winslet have to end up with a dude?

I know, I know, it’s a romantic comedy, and I should get over it.

28 Does anyone NOT cry when Eli Wallach enters the full, applauding auditorium at the Writer’s Guild of America event?

The answer is “No,” unless they are a heartless sea urchin.

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29. Why does Cameron Diaz think running is faster than driving??

I have never understood why Cameron tells her driver to turn the car around before deciding that it would be faster to run across the icy road in her stupid high heels. Once again, Cameron, you’re displaying a flagrant disregard for all safety, and I wish you would just calm down and let that driver just drive because he already does so freaking little of it.

30. But really, what is Kate Winslet doing in this movie?

The Holiday is a perfectly charming and serviceable romantic comedy on its own — but Kate Winslet’s character is leaps and bounds above everyone else in this movie. Her performance alone raises the emotional value of this film by a significant amount, mostly because she just really f*cking commits. The movie ends up feeling like all of the other characters are merely auxiliary fixtures in Kate Winslet’s damn world, because not only is the character of Iris undeniably charming (albeit a tad earnest), she’s also the only person who makes a true character shift that exists outside of her capability to fall in love. If Kate Winslet’s character didn’t exist, it would be much easier to make fun of this movie. As it is, I found my cynical self at something of a loss — because, despite some small, embarrassing creative choices, this movie really does hold up, even ten years later.


Related-ish: Just 12 Things People Love To Hate About ‘Love Actually’

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