* CrowningMomentOfHeartwarming: the homage to Arthur Abbott by the Writers' Guild of America.
** Arthur consoles Iris over dinner.
* CrowningMomentOfAwesome: Iris seizing control of her life by [[spoiler: throwing Jasper out of the house.]]
* CrowningMusicOfAwesome: The soundtrack, composed by Music/HansZimmer, really adds to the atmosphere of the movie.
** Miles even shills Zimmer briefly.
* CrackPairing: You have to admit that Jack Black and Kate Winslet isn't a pairing you'd ever expect in any movie. That it ''works'' is definitely to the film's credit, unconventional as it may be.
* FandomRivalry: With ''Film/LoveActually''. Even people who don't like ''The Holiday'' think it's a better film.
* HarsherInHindsight: Amanda trying to make herself cry and failing isn't as easy to watch when it's revealed why she can't cry. [[spoiler:When she was fifteen, her parents broke up, her father moved out, and she cried herself to sleep that night, and for many nights afterwards.]]
* HilariousInHindsight: There's a fake trailer for a film starring Lindsay Lohan and James Franco. In ''Film/ThisIsTheEnd'', Franco thinks he is stuck on Earth after the Rapture because he claims to have slept with Lohan.
* TheWoobie: All four leads have hints of this.
** Iris is possibly the biggest example. She was stuck in UnrequitedLove with Jasper ''for three years'', was too in love with him to be angry at him for cheating on her, was unable to move on with her life because of it, and ''then'' she found out he was to be engaged to TheOtherWoman. ''Ouch''. Even though both events are slightly PlayedForLaughs, can you really blame Iris for breaking down in tears and then almost ''committing suicide'' over it?
** Graham falls into this territory too [[spoiler:when Amanda finds out he's a widower.]] Also, when he admits he loves Amanda, he has tears in his eyes and she's not sure how to react. You almost can't help but get teary-eyed at that too.
** Amanda, especially when you find out about her backstory. [[spoiler:Her parents divorced when she was fifteen years old and she has been UnableToCry since because of how she cried herself to sleep the night her father moved out and convinced herself she needed to toughen up. She can't see how a long-distance relationship with Graham will work, trying to keep him at arm's length for much of the film, didn't expect him to actually fall in love with her, and finally breaks down in tears at the end when she realizes she loves Graham and wants to stay for New Year's Eve.]]
** Miles. [[spoiler:He becomes this during the video store scene when he discovers Maggie has been cheating on him. (She ''had'' gone to New Mexico as she said she had done to film for her new indie film, but she had returned after only two days there and she had been staying with the other guy ever since.) What makes it worse for Miles was that he had sent her Christmas gift to Santa Fe the day before because that's where he thought she was, and now he knows she won't receive it. Fortunately for him and Iris, it brings the two of them closer together.]]