Romancemas Day 12: The Holiday

We're at the end of our 12 Days of Christmas Rom Coms and watching a favorite starring, among others, Kate Winslet and Jack Black.

By Trisha Bartle

Updated 18 hours ago, December 25, 2024

On the 12th and final day of Romancemas, we’re watching arguably one of the best Christmas (and Hanukkah) rom-coms–especially if you ignore one half of the storyline.

Merry Christmas! If you celebrate the holiday, you may have already opened gifts, ate yummy treats, and are now trying to decompress after all the hustle and bustle. Since this is the last day of Romancemas, I thought we’d watch something classic: The Holiday (2006). At this point, it’s become a staple of my and other’s annual holiday traditions, so of course it had to make the list.

Check out the full Romancemas schedule here!

Let’s watch The Holiday!

Official Day 12 outfit: The coziest thing I could find–plaid pajama pants and a “Santa Paws” holiday puppy t-shirt.

I’ve seen The Holiday so many times over the past 21 years. Although I love it just as much as I did in the beginning, what I loved has morphed and changed. See, this story is split into two. As Amanda (Cameron Diaz) and Iris (Kate Winslet) swap houses for the holiday, we alternate between each of their stories. Amanda meets handsome Jude Law and they fall in the typical rom-com insta-love. Iris instead becomes friends with Jack Black’s Miles while she spends most of her holiday helping her elderly neighbor get physically fit for his event.

In the beginning, I liked both stories pretty equally. It’s almost like Amanda’s story is the fantasy while Iris’s is the reality. While I identified more with Iris, I still appreciated parts of Amanda’s story, too. Finding out that Jude Law’s Graham isn’t dating multiple women but is instead an adorable single father was a nice touch. Plus, when he puts on glasses after their first night together? Swoon.

But now? I have to say, I have lost almost all of my love for Amanda’s side of this movie. While Cameron Diaz is great, the style of her acting doesn’t seem to fit the rest of this movie. And, I’m sorry, but the fact that Graham is telling her he loves her after, at most, two weeks is not the green flag it used to be. Their love story lacks substance. But Iris and Miles? They’re what make this movie so great.

At this time, Hollywood hadn’t really realized how much of a stud Jack Black truly is. He’s perfect. When Miles says that he used “only the good notes” for Iris’s song? When he listens and empathizes with her story of unrequited love? When he befriends her group of old Hollywood men and joins them for Hanukkah dinner? When he’s silly in the best way while they rent movies? And, best of all, when he waits for both of them to be emotionally available to make his move? This half of the movie is everything.

Spoiler alert. (But at this point, you should have already watched the movie anyway. Let’s be real.) When Miles asks out Iris at the end of the movie, after they’ve become friends, after they’ve gotten closure from the people who didn’t deserve them in the first place, you see Iris looking so thrilled. And it’s so believable. Because Iris and Miles are on the same level. Kate Winslet and Jack Black are both catches, and may we all have a love like theirs. (Or their characters. You know what I mean.)