Five Romantic Movies to Watch on Valentine’s Day

For this Valentine’s Day edition of W Movie Club, our editors share some of their favorite films about love, in all its forms:

Uptown Girls (2003)

While Uptown Girls does feature a turbulent romance between Brittany Murphy’s character Molly and Jesse Spencer’s Neal, the real love affair is between Molly and Ray, played by a young Dakota Fanning. The unlikely duo come into each other’s lives after Molly discovers that the trust fund her late rockstar father left her was drained. In need of money to support her lavish lifestyle, her friend (played by Clueless castmate Donald Faison) connects her with a nanny job. Enter Ray, an eight-year-old hypochondriac who clashes with Molly’s carefree attitude. Throughout the film, you see Molly and Ray learn from each other: Molly learns responsibility and Ray learns to let go a little. No rom com would be complete without some sort of serenade, so stay tuned for a swoon-worthy number. Another romantic aspect of the movie? Watching scenes that were filmed on the streets of a pandemic-free New York City. ––Jenny Oliver

Indiscreet (1958)

After the beautiful opening title sequence, feast your eyes on nearly two hours of Carey Grant and Ingrid Bergman. Indiscreet is visually stunning (it’s one of the first to use split screens as a cinematic effect), and so are Grant and Bergman, who play a helplessly in love pair who embark on affair of sorts after Anna (Bergman), an actress contentedly resigned to single life (she is introduced in the film putting on her cold cream and eating some night cheese…with a glass of milk? It was the ‘50s, I guess), has a meet-cute with Philip (Grant)—only to discover he’s married. Indiscreet is clever and sophisticated, and available to stream on the Criterion Channel. —Brooke Marine

Howl’s Moving Castle (2004)

This movie always gets me more misty-eyed than any run of the mill rom com, and since it’s been trending lately on TikTok, I gave it another watch while I was snowed in a few weeks ago. It’s not the most typical love story: girl meets mysterious sorcerer, girl gets turned into an old woman by a jealous witch, girl goes on an adventure through her war torn country to break the curse. While often considered the least original story of the Studio Ghibli films—it was loosely adapted from the novel by Diana Wynne Jones—the intricate animation makes up for what it might lack in plot structure and pacing. The original voice acting and English dub are both excellent—with the latter including Billy Crystal, Lauren Bacall and a young Christian Bale. It’s a sweet tale about true love and inner beauty, but it also reflects the love we develop for our chosen families. —Tilden Bissell

Romeo + Juliet (1996)

As a less saccharine alternative, Baz Luhrmann’s ecstasy-tinged take on Shakespeare’s greatest love story is a fun option whether you’re spending Valentine’s alone, with your SO, or just drinking wine with your friends (over Zoom, of course). Chaotic and campy, it’s a who’s who of ‘90s movie stars, with Leonardo DiCaprio, Claire Danes and Paul Rudd all speaking in iambic pentameter as they run around “Verona Beach.” The costuming is still referenced in pop culture to this day (see: Jules in Euphoria’s Halloween episode), plus it has all the lavish production design you’d expect from the creator of Moulin Rouge and Strictly Ballroom. Cultural impact aside, the whole thing doesn’t totally hold up 25 years later. But Romeo and Juliet’s iconic meet cute at the fish tank alone makes it well worth a watch. —TB

While You Were Sleeping (1995)

My first celebrity crush was Bill Pullman. I can’t explain why, at age 10, I wanted to marry him, but the hearts wants what it wants. And that’s the central theme behind this vastly underrated 1995 romcom, which stars Sandra Bullock as Lucy, a lonely single cat lady. As in, she owns one single aloof cat, as if to highlight her deceased dad and lack of a boyfriend. She’s a Chicago Transit Authority token taker, passing the time between coin jangles and rush hours by crushing afar on El train regular Peter Callaghan (Peter Gallagher). One day, he’s mugged on the platform and falls into the tracks — Lucy springs into action to save him from certain death, and accompanies the comatose Peter to the hospital. There, she pretends to be his fiancé so she could visit him in the ER, when his entire very Midwestern family shows up. Lucy gradually becomes accepted into the Callaghan clan, and becomes especially close to younger brother Jack, played by Pullman. Naturally, Lucy’s feelings for Jack become conflicted as she tries to keep up the ruse as Peter’s betrothed. It’s a quiet, wintry film that examines why we love the people we do, even when we’re not “supposed” to love them, and how loving someone means loving every aspect of their lives, beyond the two-second glance as you wait for the train. — Meagan Fredette

Related: W Movie Club: ’90s Rom Coms, Real-Time Experiments, and Artsy European Fare