1Valentine's Day
Amazon Prime//Warner Bros.Couples and singles navigating the ups and downs of love on the most romantic day of the year is the premise of this interconnected story. With an all-star cast including Jessica Alba, Ashton Kutcher and Jamie Foxx to name a few, the 2010 release packs major star power.
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2Sylvie's Love
Amazon PrimeWhen Sylvie meets a saxophonist at her father’s record store, they instantly bond over music. When they’re reunited years later, their chemistry hasn’t missed a beat, but their timing couldn’t be more wrong.
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350 First Dates
Sony PicturesThe unofficial queen of romantic comedies, Drew Barrymore doesn’t disappoint in this endearing rom-com. Barrymore plays Lucy Whitmore, an attractive and bubbly woman who falls for playboy Henry Roth, portrayed by funnyman Adam Sandler, but there’s one problem: she suffers from short-term memory loss. In order to woo her, Henry has to prove his love over and over again in this light-hearted love story.
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4The Sun Is Also a Star
Warner Bros.Yara Shahidi shines in this remarkable display of young love that unfolds in a single day. Co-starring Riverdale actor Charles Melton, the New York City-based tale also touches on the sensitive and heart-wrenching aspects of deportation that are rarely depicted on the big screen.
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5The Perfect Find
NetflixBased on a Tia Williams novel of the same name, this rom-com centers around Jenna (Gabrielle Union), a fashion editor who finds herself in a May-December romance with her boss’s son (Keith Powers).
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6Moonstruck
Amazon PrimeLove may not always come wrapped in a perfect bow. Cher stars in this romantic comedy as a widow who falls for her new boyfriend’s unassuming, wild brother. Nicolas Cage also stars in this late ‘80s classic.
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7Waiting to Exhale
DisneyFour friends navigate dating, marriage, divorce and everything in between in this soulful film about the power of love and unwavering friendship.
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8Long Live Love!
M PicturesJust when a couple almost calls it quits, one partner is diagnosed with a case of amnesia. To rekindle his memory, he uses photos to help him remember the love he's on the brink of losing.
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9Your Place or Mine
NetflixReese Witherspoon and Ashton Kutcher star in this bicoastal story of love and friendship. The two best friends swap homes in different cities to find out what they really want in life.
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10Brown Sugar
DisneyHip hop is at the heart of this refreshing tale of childhood friends who bond over rap and dope beats. But is there something more? Sanaa Lathan, Taye Diggs and Queen Latifah star in the 2002 music-centric movie.
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11Pretty Woman
DisneyJulia Roberts and Richard Gere shine in this modern-day Cinderella-like movie. Directed by Garry Marshall, the 1990 film tells the familiar story of an unlikely pair who falls head over heels for one another.
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12The Fault in Our Stars
20th Century StudiosA terminally-ill teenager falls deeply in love with a patient who's also battling his own illness in this adaptation of a best-selling novel of the same name.
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13Love & Basketball
Warner Bros.All’s fair in love and basketball. Directed by Gina Prince-Bythewood, this romantic drama follows childhood friends (Sanaa Lathan and Omar Epps) whose passion for basketball intensifies along with their love for one another.
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14The Notebook
New Line CinemaRyan Gosling and Rachel McAdams star in this swoon-worthy romance about young love and the challenges that come with class and status. Set in the 1940s, the 2004 film is based on Nicholas Sparks’ best-selling novel of the same name.
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15When Harry Met Sally
Warner Bros.Can men and women keep things strictly platonic? That’s what the title characters played by Billy Crystal and Meg Ryan soon find out in this timeless tale of chance encounters, love and friendship.
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16Brokeback Mountain
Amazon Prime//UniversalSet in Wyoming in the 60s, this story of forbidden love follows two cowboys over decades as they try to navigate their feelings for one another in a world they fear won’t be receptive to their romance.
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17If Beale Street Could Talk
Annapurna PicturesAdapted from the best-selling James Baldwin novel of the same title, this 2018 film balances the beauty of budding intimacy with the ugliness of systemic racism. Like the book, the movie is set in New York City during the 1970s and tells the story of a young couple faced with unimaginable circumstances that test their love.
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18Love, Simon
DisneyThis coming-of-age film follows gay high school student Simon Spier who's fallen for an anonymous online admirer. The only problem? He hasn't come out to his family or friends. Nick Robinson stars in this award-winning movie.
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19Coming to America
When an African prince comes to New York City to find his princess, he’s met with a major culture shock that’s hilarious and heartfelt in this classic fish-out-of-water rom-com.
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20Crazy Rich Asians
Warner Bros.Based on Kevin Kwan’s best-selling book of the same title, this film adaptation follows native New Yorker Rachel Chu (Constance Wu) as she meets her boyfriend’s insanely wealthy family in Singapore for the first time.
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Karla Pope is a longtime writer, editor and blogger with more than two decades of editorial experience. She’s written for a variety of outlets including Good Housekeeping, Woman’s Day, Travel + Leisure, Tripadvisor, People, Parade and more. Her coverage includes travel, lifestyle, entertainment and wellness content. When she's not exploring the world with her family, you can find her curled up on the couch watching a documentary and eating gummy bears.
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