I may be 40-something, and married with kids, but I still love my rom-coms like I love chocolate, and the holiday flicks the most. In fact, I wrote my first novel to the tune of the holidays, watching my favourite rom-coms and crying into my Kleenex boxes. So, I’m so excited to share my favourite holiday rom-coms with you here. Put on your coziest PJs, grab some Christmas cookies and a blanket and don’t forget that Kleenex box—for the happy tears!
Obvi! This one tops my list, and not just for Cameron Diaz’s wardrobe and the house envy: Kate Winslet’s charming little cottage or Cameron’s sprawling Hollywood pad? I’ll take both. This movie has a best friend feel that I love, even though the two protagonists don’t meet until the end. (Spoiler alert?) Jack Black and Jude Law are swoon-worthy as the love interests, and the two location settings make for great armchair travel. A pitch perfect holiday flick by the master of rom-coms, Nancy Meyers.
Get ready for the ultimate holiday love fest with this ensemble comedy. Hugh Grant is brilliant as always as the Prime Minister of England, and totally believable as he falls for his adorable new assistant. An awkward Colin Firth falling for his non-English speaking cleaning lady is also sweet to watch, as we cheer the two hapless lovers on. But it’s the Keira Knightley story line that steals the show, with her as the object of affection for a pre-Walking Dead Rick (yes!), played by a then-baby-faced Andrew Lincoln.
Bridget Jones’s Diary
Hugh Grant and Colin Firth also star in this hilarious flick, featuring Renée Zellweger as the Bridget Jones. Bookended by the holidays from start to finish, the film starts with Bridget walking in the snow on New Year’s Day, in her “32nd year of being single.” She travels home for her family’s holiday party, where she reunites with an awkward childhood friend, Mark (Firth), ugly sweaters and all, and slowly falls in love with him. Trouble comes in the form of her charming boss (Grant), who strings her along. The real love story, though, is between the audience and Zellweger, for her honest, hilarious depiction of Bridget, a 30-something single woman searching for a “nice, sensible boyfriend to go out with.”
This one features another stellar cast, and Reese Witherspoon and Vince Vaughn are a match made in comedy heaven. A young couple in love visit their divorced parents over the holidays. The twist comes from the fact they are happily not married—or are they? As they go home for Christmas, visiting with their less-than-perfect families and past, they begin to wonder: How much do they really know and love each other? And should they get married? A ton of cameos, including Mary Steenburgen, Kristin Chenowith and Jon Favreau, round out the laughs.
When Harry Met Sally
Meg Ryan’s hair sure is looking dated these days, but still this classic stands the test of time. Exploring the Men Are From Mars, Women Are From Venus dynamics between men and women, Meg and Billy Crystal are friends who try (and fail) to not let sex get in the way of their friendship. Besides the will-they-won’t-they tension, there are so many great one-liners in this gem.
Meg: “I’m difficult. I’m too structured. I’m completely closed off.”
Billy: “But in a good way.”
Meg: “And I’m gonna be 40!”
Meg, crying: “Some day!”
When it comes to one-liners, it’s hard to beat Ryan Reynolds’ quick delivery. His pre-Deadpool rom-com film Just Friends is packed with them. Featuring Amy Smart as Ryan’s high school crush, the story follows Ryan (“Chris”) as he returns home for Christmas, hot and successful, and tries to win back his former bestie who turned him down back in high school (“You’re like a brother”), turning him into a big-time womanizer. It’s a hilarious trip down memory lane we can all relate to.
A Bad Moms Christmas
Okay, so this isn’t a rom-com per se, but what kind of holiday flicks for moms round-up would this be if we didn’t include it? This holiday, the grandmas come home to show the moms how to do the holidays right. The moms won’t take their Christmas hijacking lying down, though, and there are plenty of hijinks, and cute guys (including This Is Us’ Justin Hartley as a dancing Santa), to keep us entertained along the way. As Kathryn Hahn says, “Let’s put the ass, back in Christmas.”