The 10 Sweetest Moments In The Holiday (2006)

Christmas movies are generally full of romance and sweetness, but few of them are as romantic and as sweet as the 2006 cheesy classic The Holiday. Starring Cameron Diaz, Kate Winslet, Jude Law, Jack Black, and Eli Wallach, the story of two women swapping places for the holiday season is one of the most beloved Christmas movies of all time, no matter how corny and cliche it may be.

But though the film relies heavily on conventions of both romantic comedies and Christmas classics, The Holiday also manages to be uniquely its own movie, thanks in large part to the strength of its main characters. Here, we take a look back at the ten sweetest moments in this movie full of feel good scenes.

10 Mr. Napkin Head

Single dad Graham gets plenty adorable moments with daughters Sophie and Olivia, but few of them are as hilarious and goofy as the reveal of his alter ego: Mr. Napkin Head. After Amanda arrives at Graham’s home unexpectedly, Graham is forced to introduce her to his daughters, who quickly enjoy revealing new parts of their father’s personality to his girlfriend.

Despite initial protests on Graham’s part, he is easily convinced to reveal his Mr. Napkin Head alter ego by his enthusiastic daughters. And of course, it’s quite simply what the name suggests: Graham “wearing” a napkin on his face, beneath his glasses. Adorable, ridiculous, and exactly the kind of joke a dad would make.

9 Iris & Miles composing together

While many fans of The Holiday gravitate toward the romance between Graham and Amanda in England, the Los Angeles-based friendship turned courtship between Iris and Miles is actually the source of many of the film’s sweetest moments.

In one particular scene, Miles casually tries to impress Iris with his composing skills, revealing that not only has he created a composition inspired by their friend Arthur, but also a sweet love melody inspired by Iris, too. What follows is a hilarious symphony of “doodly-doos” and “schmoodly-doos” as the two friends laugh and compose side by side.

8 “Don’t blow away”

Speaking of Iris and Miles, when it comes to the romantic meet cutes in the movie, these two have the market cornered. When Miles, a friend of Amanda’s ex-boyfriend, comes to collect some of said ex’s things from Amanda’s house, he’s instead greeted by holiday guest Iris.

The two meet in the middle of a Santa Ana wind storm, resulting in Iris getting something caught in her eye, and Miles gently (and quite adorably) brushing it out for her while explaining the Santa Ana wind phenomenon to her. His parting words of advice to her? “Don’t blow away.” Sweet, adorable, and swoon-worthy.

7 Graham & Amanda reunite

Amanda’s emotional journey in the film is driven by many things, but one particular theme that runs throughout the movie is her inability to cry. No matter her attempts to be moved by things, she’s never been able to shed a tear since her parents split up when she was younger. But all of that changes when she meets, and briefly loses, Graham.

As she prepares to leave the countryside to head back to LA, Amanda has a change of heart, weeping in the back of her cab before she literally runs back to Graham’s cottage to find him, adorable and weeping as well. The elated hug they share is one of the film’s most romantic moments of all.

6 Iris helps Arthur get in shape

Though The Holiday is a romantic comedy, arguably the film’s best and strongest relationship is the one Iris develops with her temporary neighbor, the elderly Hollywood legend Arthur Abbott (played by actual Hollywood legend Eli Wallach). During their time together, Arthur learns that he will be honored with a lifetime achievement award during a ceremony he feels unfit to attend due to his old age.

That’s where Iris comes in, determined to whip him into physical and emotional shape so that he feels the award is one he’s earned and a ceremony he can look forward to. What follows is an adorable montage of their friendship, including playful back and forth exercises, and laps in the pool.

5 Amanda meets Sophie & Olivia

Amanda and Graham’s romance is never officially given any labels for the first half of the film, given both of their levels of discomfort with relationships. But everything changes when Amanda finds herself unexpectedly meeting Graham’s two young daughters, Olivia and Sophie.

Having previously believed that the two names belonged to other girls Graham had been seeing, Amanda is totally stunned by the revelation that he’s a father. But the girls are immediately taken with Amanda, and eager to invite her into their little world, no matter how awkward the first encounter may be for their father.

4 Iris meets Arthur

As we’ve already established, the relationship between Arthur and Iris is the real highlight of the movie, and that’s beyond clear from the first moment these two interact. In their own bittersweet but undeniably sweet meet cute, Iris comes across Arthur when he’s lost his way on the way home.

Knowing where he lives, Iris is able to swoop in like his own knight in shining armor, offering him a ride home and quickly establishing an adorable rapport as they bond over their histories and interests on the way.

3 “You’re supposed to be the leading lady of your own life!”

Iris is dealing with some pretty heavy emotional baggage at the start of the film, having been manipulated and taken advantage of for years by Jasper, the not-quite-love interest who was never really truly interested in her. Arthur is the first person to get through to her regarding this issue, succinctly summarizing Jasper as a schmuck.

But beyond that, Arthur sees through to the heart of Iris’s problems in only the way a writer would be able to: “Iris, in the movies, we have leading ladies and we have the best friend. You, I can tell, are a leading lady. But for some reason, you’re behaving like the best friend.” His keen observation leads Iris to make her own: “You’re supposed to be the leading lady of your own life!”

2 The tent scene

The relationship between new couple Graham and Amanda, and Graham’s young daughters Sophie and Olivia, is one that the film doesn’t explore until it’s nearly half over. But as soon as it does so, the sweetness and cuteness are almost unbearable, and that’s the most clear in the sweet sequence that finds all four characters snuggling in the lofty tent set up in the girls’ bedroom.

Between the girls admiring Amanda’s lipstick and telling her she’s lovely, to Graham and Amanda’s furtive smiles and secret hand holding, everything about this scene works, and every moment is even sweeter than the last.

1 Arthur’s award ceremony

The Holiday is a movie that’s determined to give all of its characters happy endings. But for all its romantic drama, there’s no character who deserves a happy ending more than Arthur. After his lifetime of work, and the efforts he’s undertaken to prepare himself to be honored on a night all about him, Arthur is nearly overwhelmed with emotion when Iris brings him to the award ceremony.

But from start to finish, Arthur is more jolly, more sprightly, more loved and vibrant than ever before in the film, as he finally allows himself to be the leading man in his own story.

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