While You Were Sleeping
Sandra Bullock has never been more endearing than when she plays Lucy, a lonely transit worker who saves the life of her crush as he falls on the train tracks. Trouble is, his family mistakenly believes she’s his fiancé as he lays in a coma afterward.
The only one who’s skeptical is Peter’s brother, Jack (Bill Pullman), who doesn’t think Lucy is what she seems … and also seems to be falling for her. The Bullock factor, the crazy misunderstanding, and the funny family make this one a holiday favorite—not to mention the chemistry between Lucy and Jack.
Giant Mechanical Man
The twist is Tim is a performance artist, the Giant Mechanical Man who disguises himself in silver paint and stilts to pose around their city that winter to make others feel less alienated. He warms Janice’s heart, but she doesn’t know he’s also the sanitation guy at the zoo where she works. This romance is a win for those of us who love quirky love stories with a blend of humor and poignancy.
Love it or hate-watch it, no holiday season is complete without seeing this ensemble film all about love, snow, and Hugh Grant playing the British prime minister in a pre-Brexit world. Sure, it’s got its issues and about fifteen too many fat jokes, but where else can you find such a fabulous British cast and a nativity play with lobsters?
It’s such a medley of emotions, characters, and modern love, you’re bound to find at least one storyline that makes you tear up or smile.
You've Got Mail
Rom-com royalty Meg Ryan and Tom Hanks are at the top of their game in this 90s retelling of The Shop Around the Corner. Kathleen and Joe are both in the bookstore business, except Joe’s part of a big corporation that threatens to put small bookstores like Kathleen’s out on the street. So in real life, they’re nemeses.
But on their computers they’ve been talking over AOL and growing closer without knowing each other’s real identities. Though the film lasts through multiple seasons, there are particularly fun scenes set around the holidays, including when Joe first realizes the person he’s been emailing with is actually the woman he refers to as “a pill.”
The Cutting Edge
Enemies-to-lovers romance has never been so fun as this 1992 movie about two people who can’t get along, but somehow become magic on the ice together. Kate (Moira Kelly) is an uptight figure skater who reluctantly teams up with injured hockey star Doug (D.B. Sweeney) to compete in the Olympics.
Unfortunately, they hate each other. If you haven’t watched this one in years, it might be time for a rewatch, if only for the ice-melting moments between these two opposites that attract.
If you’re dreaming of escaping somewhere else for the holidays but have spent your money on one too many peppermint mochas, watching 2006’s The Holiday may give you a vicarious thrill.
In it, Englishwoman Iris (Kate Winslet) and American Amanda (Cameron Diaz) decide to swap homes for the holidays and wind up finding love with men played by Jack Black and Jude Law, respectively. It’s funny and adult and lovely, and Jack Black is especially charming as an unconventional romantic lead.
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Winter love has never been so magical, or so frustrating, as this Kate Beckinsale/John Cusack romance about destiny and choice. Jonathan meets Sara, and sparks fly. Unfortunately, Sara is a hardcore believer in fate and all signs point to making the two wait years and the audience over an hour for them to end up together.
Good thing there’s a fun supporting cast of friends like Jeremy Piven and Molly Shannon to prop up the would-be lovers as they schlep across the county, up and down elevators, and across ice rinks in search of a soul mate.
Bridget Jones's Diary
Though this rom-com covers a year in the life of the Bridget we know and love, it’s bookended with brilliant holiday scenes, starting when Bridget (Renee Zellwegger) meets Mark Darcy (Colin Firth) while he's wearing a horrible reindeer jumper.
Through the hilarious movie, Bridget’s feelings for Mark grow from dislike to grudging respect to finally love. And in one of the film’s most romantic moments, Darcy admits to liking her “just as [you] are.” That’s worth braving a turkey curry buffet for.
Holiday in Handcuffs
Mario Lopez is kidnapped by Melissa Joan Hart and brought home to her family for the holidays. If that isn’t enough to add this movie to your holiday romance rotation, I don’t know what is.
Holiday in Handcuffs takes the popular fake boyfriend trope and tosses in two actors we grew up watching, family dysfunction, and a whole lot of awkwardness by gunpoint. It’s like the Christmas you’ve always dreamed about.
There’s no better way to ring in the holiday season than by putting on White Christmas while you shop online. There’s so much to love about this classic, and it’s got double the romance as two showgirl sisters (played by Rosemary Clooney and Vera-Ellen) fall for two former soldiers, Bob (Bing Crosby) and Phil (Danny Kaye).
Along the way, the 50s film packs in much nostalgia with musical numbers, a heartwarming story, and a final snow scene that’s worth waiting for.
Featured still from "While You Were Sleeping" via Buena Vista Pictures