News Pop Culture and Entertainment The 14 Best Movies to Watch on Valentine's Day An entire movie marathon of romance. By Christopher Luu Christopher Luu Instagram Twitter Christopher is a Southern California-based editor and has been with InStyle since 2018. He covers all things entertainment, celebrity, and culture. InStyle's editorial guidelines Published on January 29, 2021 @ 01:00PM Pin Share Tweet Email Valentine's Day got you down? No matter your relationship status, the hearts, and flowers can push just about anyone to retreat from the over-the-top celebrations — whether there's a stay-at-home order or not. If you're looking to check out some holiday-appropriate rom-coms, romantic movies, or throwback favorites, here are 14 of the best. Always Be My Maybe Ali Wong, Randall Park, and Mariah Carey? It's the only love triangle to hope for this Valentine's Day. Oh, if that wasn't enough, there's a Keanu Reeves cameo, too. This Netflix rom-com is clever, charming, and has so many '90s throwbacks that it belongs in the canon alongside just about every Julia Roberts and Sandra Bullock classic. To All the Boys: Always and Forever The third installment of Lara Jean's erstwhile love letter-writing campaign, Netflix's To All the Boys: Always and Forever (out on February 12) follows To All the Boys: P.S. I Still Love You and To All the Boys I've Loved Before. The series may lean a little young, but that doesn't mean that it's not the perfect trilogy to watch during Valentine's Day weekend. It's saccharine-sweet and feel-good in the best way. Sleeping with Other People Allison Brie and Jason Sudeikis star as two people who happen to have issues with monogamy and meet at a sex-addicts anonymous support group. No, this isn't your usual rom-com. Instead, it replaces tired tropes with raunchy jokes, sex positivity, and all the charm and laughs that you'd expect from comedy vets Brie and Sudeikis. Valentine's Day The cast reads like the guest list at the Vanity Fair Oscar party — Jennifer Garner, Julia Roberts, Jessica Biel, Ashton Kutcher, Topher Grace, Shirley MacLaine, Bradley Cooper, Taylor Swift, Jamie Foxx, and Anne Hathaway — but the film focuses on one Valentine's Day in L.A. All the faces are familiar and so are some of the situations, but that makes for a fun romp through some classic V-Day moments that'll make viewers reach for those chalky heart-shaped candies. 50 First Dates Drew Barrymore and Adam Sandler's instant classic brings a slapstick twist to rom-coms and romance. Think: Groundhog's Day meets Valentine's Day plus plenty of tropical vistas and Barrymore's signature cute, girl-next-door charisma. Laughs and love come standard — and so does the desire to watch The Wedding Singer and Blended, two other Sandler-Barrymore gems. The Princess Bride This romantic romp through fantasy and fairy tale settings stars Cary Elwes and Robin Wright. It's a cult favorite for a reason. Namely, people love it because it's funny, heartwarming, and it's now available on Disney+. Anyone bored of the usual romances and rom-coms can escape to this classic. Failure to Launch Sarah Jessica Parker leaves New York and her Manolos behind to star alongside Matthew McConaughey in this tale of a man-child living at home and all the hijinks that come with that not-so-unfamiliar situation. This is McConaughey at his rom-com best and fans of Sex and the City can find plenty to love from SJP, even when she's not Carrie Bradshaw. 10 Things I Hate About You '90s teen romances were a bonafide trend, but the crown jewel is undoubtedly the Julia Stiles and Heath Ledger classic 10 Things I Hate About You. A modern (well, pre-2000s) take on William Shakespeare's The Taming of the Shrew, there's a bad boy, a reluctant cool girl, and, yes, a prom to top it all off. The Proposal Come for Sandra Bullock and Ryan Reynolds in two very typical roles (high-strung, high-powered female C-suite type-A and six-pack good guy with a quirky family), stay for Betty White. Now that Sandy B and Reynolds have stepped away from romantic films, this time capsule of laughs and love is a favorite no matter what time of year it is. This Means War A love triangle never looked this glossy — and that's because music video director McG helmed this Tom Hardy, Reese Witherspoon, Chris Pine ensemble action-romance. Two spies end up falling for Witherspoon, which makes for an explosion-filled, over-the-top flick that's easy, breezy, and won't have anyone reaching for tissues. Dirty Dancing Before all the remakes, the classic Dirty Dancing introduced the world to Baby, "Time of My Life," and a very risky lift that's been a standby for every season of Dancing With the Stars. Critics will say that this flick doesn't stand the test of time, but they're just not giving into the power of dance. Friends with Benefits Justin Timberlake and Mila Kunis star in an anti-com-com, where their characters choose to go against every dating cliché, only to find themselves deeply immersed in a movie that follows just about all of them. There's a flash mob. There are sexy moments involving Timberlake's abs. There are even sweet moments, but really, it's about the flash mob. Up in the Air George Clooney and Vera Farmiga find love at 30,000 feet, where turbulence and frequent flyers rule, not romance. Critics loved the unpredictable nature of the flick, which is anything but the average rom-com — and earned Anna Kendrick (and the film's other stars) just about every award nomination back in 2010. Fifty Shades of Grey There's no shame in checking out this cultural touchstone, which stars Dakota Johnson and Jamie Dornan and the infamous Red Room. Nobody would call this trilogy a cinematic masterpiece, but it has become fodder for drinking games and memes, so watching any of the three movies can be more about the experience than the critical acclaim.