The Holiday features the related (though, fortunately, untangled) romances of Amanda Woods (Cameron Diaz) and Graham Simpkins (Jude Law) as well as Iris Simpkins (Kate Winslet) and Miles Dumont (Jack Black). Both romances are unlikely, due to the strange situation presented, but somehow...believable and satisfying.
At the top of the film, Iris is desperately in love. So in love that she can't think about anything else, talk about anything else, her entire life revolves around the man that she had been seeing. A man that had cheated on her in the past, and a man who is no longer hers. The two are still having what would be considered an affair -- at least until she's given the task of writing about his engagement. This sudden news drives Iris to switch houses for the holidays with Amanda, who lives halfway across the world.
One of the first people that Iris meets when she gets to Los Angeles is Miles, who knows Amanda through her ex-boyfriend. Miles and Iris end up becoming friends when the two find themselves invited to an impromptu Hanukkah party thrown by the neighbours.
While Miles has a girlfriend, there's a good amount of friendly flirting going on between him and Iris, though it seems purely innocent and light. It's only when Miles sees his girlfriend with another man, and learns that Iris's ex is keeping her on the hook through his continued contact with her on vacation, that the two vow to help each other get over their former lovers.
Their friendship quickly grows as they share similar tastes in music and movies, and Miles even writes a song for and about Iris to help her realize what an amazing person she is inside and out. The two seem to be falling for one another when Miles gets a phone call from his former, asking if they can talk about their relationship. Miles takes off on Iris to meet up with his ex-girlfriend, leaving Iris feeling somewhat rejected and once again heart-broken.
While Miles is off considering all the ways in which Iris is his ideal woman, Iris finds herself being accosted by her ex-lover when he shows up at her door. He asks her to take a vacation with him, but refuses to break off his engagement, finally allowing Iris to work up the gumption to tell him to get out of her life.
Miles returns to Iris, letting her know that his relationship with his ex-girlfriend is finalized, and asks if she has plans for New Year's Eve. She responds that she'll be in England, prompting him to say that he's never been, but has always wanted to go. When she doesn't take the hint, he asks if he can take her on a date when he follows her to England, and they each have similar reactions of glee.
Amanda breaks things off with her boyfriend when she realizes that he's been cheating on her; when his reason for doing so is that she works too hard, she decides that she needs a vacation in order to relieve her stress. Amanda has actually been heavily stressed since she was a child and her parents divorced, somehow breaking her soul in such a way that she was unable to cry into her adulthood.
The first social interaction Amanda has with a Londoner is Graham, Iris's older brother, who stumbles into her house after a night at the pub. Amanda uses Graham to reduce her stress by inviting him into her bed for the night, assuming that it will be a one-night stand. Her assumption seems on the spot the next morning, when she notices a woman's name flashing on his caller display.
Things between the two of them begin to grow a little more familiar as he invites her out to dinner with his friends and finds himself spending the night with her once again, but she remains stand-offish as she sees yet another woman's name showing up on his phone's display. The two of them end up spending the day together and having a first date that they both find enjoyable...until Amanda ruins things by saying that "[she's] not sure if [she] can handle complicated." Amanda returns to Graham's home that night to apologize, and, in doing so, meets his two young daughters belonging to the names flashing on his call display.
Graham reveals that he's a widower and Amanda ends up spending the evening with the family, telling stories and jokes, and enjoying the interaction with Graham's daughters. It's when the youngest refers to her family as the "three musketeers," a term that a young Amanda had used to refer to her own family before the divorce, that Amanda realizes this sense of family is exactly what she wants out of life.
Even still, Amanda is unable to bring herself to respond in kind when Graham tells her that he loves her, and can only list all of the reasons for which they shouldn't be together. It's when she can't stop crying that she decides the reasons for them to try to be together are much greater than those for which they shouldn't.
Iris and Miles became extremely good friends in a short period of time, in part because of their similar interests, but also because they were able and willing to help each other forget about their heartbreak. Their attraction to one another wasn't immediate, but they seem to work really well together as a couple.
The issue of living across the globe from one another might not be as difficult for them, as Iris is likely to want to get away from her job due to her ex, and could, in theory, find a similar reporting job somewhere in Los Angeles. But I can't imagine Miles asking her to move away from her brother and nieces, and it seems as though he would move a mountain to make her happy, so he's likely to find work as a composer across the pond to suit her needs.
They're the kind of couple that you really root for and just want to hang out with, and if the film had ended on a flash-forward to their wedding it still would have felt genuine to me.
Amanda and Graham's relationship is muddled by the fact that Amanda's job is so important to her. Even though she's likely to want to spend less time in the office if she has her family waiting for her at home, there's still the issue that she could only do her job, which she loves, from Los Angeles, and Graham would have to uproot his daughters in order to move them there.
A long-distance relationship between the two of them wouldn't work because of how upsetting that would be to the children. Both Amanda and Graham seem slightly too neurotic to make things work between them while across the globe, and it feels as though, at least to me, that if either of them were to sacrifice something from their lives for the other, that it would only be a matter of time before their relationship imploded and the children would be left to pick up the pieces.
I just don't feel that either Graham or Amanda could make the necessary changes to their lives to make their relationship work without severely damaging the lives of his children. The only way I can see this being resolved is if both Graham and Iris moved to Los Angeles in order to be closer to Amanda and Miles, because then at least the kids would have some other family in the country to turn to, but that seems somewhat unlikely. Maybe they could live half the year in America and the other half in England?
Either way, I only see one couple making it out of this movie alive.
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