25 Must-Watch Valentine's Day Movies Of All Time

Introduction

Valentine’s Day is a celebration of love, and what better way to commemorate the occasion than by watching some of the most romantic films ever made? Whether you are snuggled up with a long-term partner, hosting a "Galentine’s" party with friends, or enjoying a cozy solo night in, cinema has a unique way of capturing the fluttering hearts and crushing heartbreaks that define our relationships.

From the golden age of Hollywood to the viral sensations taking over TikTok, the best romantic movies do more than just show us a kiss in the rain. They explore the messy, complicated, and utterly transformative power of connection. In this comprehensive guide, we have curated the ultimate watchlist, blending critical darlings with fan favorites to ensure your Valentine's Day is nothing short of cinematic magic.

If you love these stories, you will fall in love with our own original romantic audio dramas. Support our work and donate here to help us keep creating new love stories. You can also listen to our episodes here for free, heartwarming entertainment.

Let’s count down from number 25 to the ultimate Valentine’s Day movie.

25. 10 Things I Hate About You (1999)

If you have spent any time scrolling through romantic movie trends on social media recently, you know that 10 Things I Hate About You remains a cultural juggernaut. A modern retelling of Shakespeare’s The Taming of the Shrew, the film is set in a Seattle high school where the popular Bianca cannot date until her abrasive, anti-social older sister Kat (Julia Stiles) does. Enter Patrick Verona (Heath Ledger), the school bad boy paid to woo Kat.

Why it is essential for Valentine's Day: It captures the enemies-to-lovers trope perfectly. The chemistry between Ledger and Stiles is electric, culminating in the iconic "Can't Take My Eyes Off You" stadium singing scene that set the bar for grand romantic gestures. It is a nostalgic trip that reminds us that love often comes from the most unexpected places.

24. The Holiday (2006)

For those who dream of swapping lives and finding love across the ocean, The Holiday is the ultimate cozy watch. Two women—Iris (Kate Winslet) in a snowy English cottage and Amanda (Cameron Diaz) in a lavish L.A. mansion—swap homes for the holidays to escape their disastrous love lives.

This film is a masterclass in the "cozy aesthetic." It is visually comforting, featuring Jude Law and Jack Black as the love interests who help the women rediscover their self-worth. It serves as a gentle reminder that sometimes you have to leave your comfort zone to find the person who truly appreciates you. If you enjoy stories about fresh starts, check out our romantic audio series for more tales of new beginnings.

23. Notting Hill (1999)

Can a regular person really date a celebrity? Notting Hill answers this with a resounding, charming "yes." Starring Hugh Grant as a bumbling bookstore owner and Julia Roberts as the world's most famous actress, the film is a British fairytale grounded in wit and vulnerability.

The film is famous for the line, "I'm just a girl, standing in front of a boy, asking him to love her." It deconstructs the glamour of fame to show that underneath the flashbulbs, we are all just looking for genuine connection. It is the perfect watch for anyone who believes in the impossible odds of love.

22. Love & Basketball (2000)

Spanning four quarters of the characters' lives, Love & Basketball is a profound look at how ambition and romance intersect. Monica (Sanaa Lathan) and Quincy (Omar Epps) are childhood neighbors who share a dream of playing professional basketball. Their relationship evolves from rivalry to friendship to a complicated, deep-seated love.

This film stands out because it treats the female protagonist's career with as much importance as the romance. It is gritty, realistic, and incredibly sexy. The "one-on-one" game for a heart is one of the most high-stakes romantic scenes in cinema history, proving that love is the only game that truly matters.

21. Amélie (2001)

If you want a movie that feels like a hug, Amélie is it. This French masterpiece follows a shy waitress in Montmartre who decides to change the lives of those around her for the better, while struggling to find the courage to pursue her own love interest.

Visually, the film is a feast of reds and greens, creating a whimsical, storybook atmosphere. It celebrates the introverts of the world—showing that quiet, quirky love is just as powerful as the loud, dramatic kind. It is a unique, artistic choice for a Valentine's Day watchlist.

20. Silver Linings Playbook (2012)

Love is rarely neat and tidy, and Silver Linings Playbook embraces the mess. Bradley Cooper plays Pat, a man with bipolar disorder trying to win back his estranged wife, who meets Tiffany (Jennifer Lawrence), a young widow with her own struggles. They bond through a dance competition that becomes their lifeline.

The film strikes a delicate balance between mental health drama and romantic comedy. It argues that two "broken" people can heal each other, not by fixing one another, but by understanding each other's madness. It is a raw, honest portrayal of finding your "silver lining" in another person.

19. Before Sunrise (1995)

This is the ultimate film for hopeless romantics who value conversation over spectacle. An American tourist (Ethan Hawke) and a French student (Julie Delpy) meet on a train and decide to disembark in Vienna, spending one night walking, talking, and falling in love before he has to fly home the next morning.

There are no explosions or grand plot twists—just two people connecting on a soul level. It captures the fleeting, intense nature of a chance encounter and the fear that you might never feel this way again. It is a must-watch for anyone who loves deep, philosophical relationship discussions.

18. Moonlight (2016)

Winner of the Academy Award for Best Picture, Moonlight is a stunning, three-part narrative about Chiron, a young Black man growing up in Miami, grappling with his identity and sexuality. His relationship with Kevin serves as the emotional anchor of the film.

While it is a heavy drama, the romance at its core is tender and aching. The cinematography uses color and light to convey intimacy in a way few films do. It is a necessary watch for its portrayal of vulnerability and the enduring power of a first love that shapes your entire life.

17. Dirty Dancing (1987)

"Nobody puts Baby in a corner." That line alone secures Dirty Dancing a spot on this list. Set in the summer of 1963, it tells the story of Frances "Baby" Houseman falling for the resort's dance instructor, Johnny Castle (Patrick Swayze).

Beyond the iconic lift, the film deals with class issues and growing up. It is about the summer that changes everything. The chemistry between Swayze and Jennifer Grey is palpable, making it a timeless favorite for anyone who loves dance and passion.

16. Brokeback Mountain (2005)

A tragic and beautiful tale, Brokeback Mountain revolutionized the romance genre. It follows two sheepherders, Ennis (Heath Ledger) and Jack (Jake Gyllenhaal), who develop a forbidden relationship in the mountains of Wyoming in 1963.

The film explores the crushing weight of societal expectations and the pain of a love that cannot be lived openly. It is a tearjerker, certainly, but it is also a stunning testament to a connection that survives decades of separation and silence.

15. Titanic (1997)

For pure, epic scale, nothing beats Titanic. James Cameron’s disaster masterpiece anchors its historical tragedy with the fictional love story of Jack (Leonardo DiCaprio) and Rose (Kate Winslet). Their whirlwind romance aboard the doomed ship is the stuff of legends.

From the "King of the World" scene to the steamy handprint on the car window, Titanic delivers grand emotional highs. It reminds us that love can be brief yet define a lifetime. (And yes, we can still debate if there was room on that door).

14. Jerry Maguire (1996)

"You had me at hello." This film is often remembered as a sports movie, but at its heart, it is a romance. Tom Cruise plays a sports agent who has a moral epiphany and loses everything, except for one client and Dorothy Boyd (Renée Zellweger), the single mom who believes in him.

It is a movie about cynicism versus optimism. The romance works because it is built on partnership and mutual respect. Jerry and Dorothy save each other, proving that love—and a little bit of "quan"—is worth fighting for.

13. Pride & Prejudice (2005)

This adaptation of Jane Austen’s novel has seen a massive resurgence thanks to social media, particularly for the scene where Mr. Darcy (Matthew Macfadyen) flexes his hand after touching Elizabeth’s (Keira Knightley). It captures the excruciating, delightful tension of repressed Victorian desire.

The cinematography is breathtaking, often looking like a moving painting. It is the ultimate "slow burn," where a single look or a touch of the hand conveys more passion than a dozen sex scenes. It is perfect for fans of literary love stories.

12. About Time (2013)

About Time is a rom-com with a sci-fi twist that will leave you sobbing happy tears. Tim (Domhnall Gleeson) discovers the men in his family can travel through time. He uses this power not to change history, but to get a girlfriend (Rachel McAdams) and perfect their life together.

However, the film evolves into a meditation on fatherhood, family, and the beauty of an ordinary day. It teaches us that the ultimate goal of love is just to enjoy the ride.

Listen to our episodes here to experience more heartwarming stories that celebrate the little moments in life.

11. Past Lives (2023)

A modern masterpiece that has taken the world by storm, Past Lives explores the Korean concept of In-Yun (providence or fate). It follows Nora and Hae Sung, two deeply connected childhood friends who are torn apart after Nora’s family emigrates from South Korea, reuniting two decades later in New York.

It is a mature, nuanced look at the "one that got away" and the life you didn't live. Unlike typical melodramas, there are no villains here—just three decent people trying to navigate complex feelings. It is a quietly devastating film about choices and timing.

10. Crazy Rich Asians (2018)

A modern romantic comedy with a fresh perspective on love across cultural boundaries, Crazy Rich Asians follows Rachel, an American-Chinese woman who discovers her boyfriend comes from an incredibly wealthy Singaporean family. Set against the lush backdrop of Singapore, the movie combines humor, romance, and dazzling visuals.

The film’s exploration of family dynamics, cultural identity, and class differences adds depth to its central love story. With its vibrant storytelling and heartfelt performances, Crazy Rich Asians celebrates the transformative power of love.

9. Portrait of a Lady on Fire (2019)

This French historical romance offers a breathtaking exploration of forbidden love between an artist and her subject in 18th-century France. The film’s restrained yet passionate portrayal of queer love is both emotionally profound and visually stunning.

With its minimalist dialogue and evocative cinematography, Portrait of a Lady on Fire creates a powerful, slow-burning love story. Its exploration of memory, longing, and artistic expression makes it a standout in the romance genre.

8. 50 First Dates (2004)

For a more lighthearted take on romance, this Adam Sandler and Drew Barrymore romantic comedy offers plenty of laughs and heartfelt moments. Henry falls in love with Lucy, a woman with short-term memory loss, and must make her fall in love with him every day.

While comedic, the film delves into themes of perseverance and devotion. Its unique premise and charming performances make it a delightful watch for Valentine’s Day.

7. La La Land (2016)

A modern musical that pays homage to classic Hollywood, La La Land stars Ryan Gosling and Emma Stone as two aspiring artists trying to balance their dreams with their love for each other. The film’s vibrant musical numbers and poignant storytelling make it a contemporary classic.

The bittersweet ending challenges traditional romantic movie expectations, offering a heartfelt exploration of ambition, love, and the choices that shape our lives.

6. Call Me By Your Name (2017)

Set in 1980s Italy, Call Me By Your Name tells the story of 17-year-old Elio and his romance with Oliver, a graduate student. This coming-of-age film is a sensitive portrayal of first love, capturing its intensity and fleeting nature.

With breathtaking cinematography and deeply moving performances, the film’s exploration of identity, vulnerability, and desire leaves a lasting impression. It’s a poignant reminder of the transformative power of love.

5. The Notebook (2004)

A quintessential romance, The Notebook follows the passionate love story of Noah and Allie, played by Ryan Gosling and Rachel McAdams. Spanning decades, the film explores themes of enduring love, sacrifice, and rediscovery.

Its iconic rain-soaked kiss scene and emotional depth have solidified its place as a modern romantic classic. The Notebook is a testament to the power of love that withstands the test of time.

4. Eternal Sunshine of the Spotless Mind (2004)

This unique romantic drama, starring Jim Carrey and Kate Winslet, offers a science fiction twist on love and memory. After a painful breakup, a couple undergoes a procedure to erase memories of their relationship, only to rediscover their love for each other.

The film’s exploration of the fragility and resilience of love, paired with its inventive storytelling, makes it a profound and unforgettable cinematic experience. It reminds us that even the most painful memories can hold beauty and meaning.

3. Pretty Woman (1990)

A modern Cinderella story, Pretty Woman stars Julia Roberts as Vivian, a sex worker who falls in love with Edward, a wealthy businessman played by Richard Gere. The film’s exploration of class differences and the transformative nature of love struck a chord with audiences worldwide.

Roberts’ charismatic performance and the film’s witty dialogue make it one of the most beloved romantic comedies of all time. Its message of acceptance and unexpected connections resonates deeply, even decades after its release.

2. When Harry Met Sally (1989)

Can men and women truly be just friends? Rob Reiner’s classic romantic comedy explores this question through the evolving relationship between Harry and Sally, played by Billy Crystal and Meg Ryan. Over the years, their friendship transforms into love, offering a witty and heartfelt take on romantic compatibility.

The film’s famous deli scene ("I'll have what she's having") and sharp dialogue penned by Nora Ephron have become iconic. Its honest exploration of love’s complexities, from the awkwardness of dating to the comfort of old friendship, makes it a timeless favorite for Valentine’s Day.

1. Casablanca (1942)

Often hailed as the greatest romance film of all time, Casablanca tells the story of star-crossed lovers Rick Blaine (Humphrey Bogart) and Ilsa Lund (Ingrid Bergman) against the dramatic backdrop of World War II. Set in the Moroccan city of Casablanca, the film is a masterclass in storytelling, exploring themes of love, sacrifice, and personal honor.

With its unforgettable lines like, “Here’s looking at you, kid,” and “We’ll always have Paris,” the movie remains an enduring symbol of romantic longing. Its blend of drama, intrigue, and unfulfilled love solidifies its place as the ultimate Valentine’s Day movie.

Conclusion

These twenty-five films showcase the many dimensions of love—from its lighthearted moments to its profound emotional depths. Whether you prefer grand Hollywood romances, quirky comedies, or poignant dramas, each movie offers a unique perspective on love’s transformative power.

This Valentine’s Day, gather your loved ones, grab some popcorn, and immerse yourself in these cinematic love stories. They remind us that love, in all its forms, is a journey worth celebrating.

If you are looking for even more romantic content to fill your heart, listen to our episodes here for free audio dramas that you can enjoy anywhere. To support our mission of bringing more love stories to the world, please consider donating here.

Call to Action: Ready to watch? Most of these films are available to stream or rent on Netflix, Amazon Prime Video, or Hulu. Check your local listings and plan the perfect movie night tonight!

FAQs

1. Why is Casablanca considered the best Valentine’s Day movie? Casablanca captures the essence of timeless love, combining romance, sacrifice, and unforgettable storytelling in a way that no other film has quite matched since 1942.

2. Are these movies suitable for a Valentine’s Day date night? Absolutely! These films cater to a variety of tastes, from lighthearted comedies like 10 Things I Hate About You to emotional dramas like The Notebook.

3. Is The Notebook based on a true story? The Notebook is based on Nicholas Sparks’ novel, which was inspired by the real-life love story of his wife’s grandparents.

4. What makes When Harry Met Sally a classic? Its witty dialogue, relatable characters, and honest exploration of the transition from friendship to love make it a perennial favorite.

5. Can I watch these movies on streaming platforms? Many of these films are available on popular streaming services like Netflix, Amazon Prime, and Hulu. Availability varies by region.

6. What sets Eternal Sunshine of the Spotless Mind apart from other romantic films? Its unique blend of science fiction and romance, along with its deep exploration of how memory shapes our relationships, makes it truly one of a kind.

7. Which of these movies is best for fans of musicals? La La Land is the perfect choice, offering stunning musical numbers and a heartfelt story about love and ambition.

8. What themes are explored in Call Me By Your Name? The film delves into themes of first love, self-discovery, and the bittersweet nature of fleeting romance set against a lush Italian summer.

9. Is Pretty Woman suitable for all audiences? While generally lighthearted, Pretty Woman contains mature themes regarding sex work and class dynamics, so viewer discretion is advised.

10. Why is Crazy Rich Asians a significant romantic comedy? Its cultural representation and fresh perspective on modern love and family duty make it a groundbreaking addition to the genre.

Looking for engaging romantic comedy content? Dive into these delightful articles that explore the charm and nuances of rom-coms:

1. 9 Rom-Coms That Will Make You Laugh and Fall in Love – Discover a selection of films that blend humor and romance seamlessly. Click here: https://www.thatlovepodcast.com/post/9-rom-coms-that-will-make-you-laugh-and-fall-in-love 

2. Top 10 Romantic Comedies of All Time – Explore a curated list of timeless rom-coms that have captured hearts worldwide. Click here: https://www.thatlovepodcast.com/post/top-10-romantic-comedies-of-all-time-that-ll-make-you-laugh-and-fall-in-love-again

3. The Best Romantic Comedies Streaming on Amazon Prime Right Now – Find your next favorite rom-com available for streaming. Click here: https://www.thatlovepodcast.com/post/the-best-romantic-comedies-streaming-on-amazon-prime-right-now 

4. The 9 Elements of All Great Rom-Coms That Keep Us Hooked – Uncover the key ingredients that make romantic comedies irresistible. Click here: https://www.thatlovepodcast.com/post/the-9-elements-of-all-great-rom-coms-that-keep-us-hooked

5. Romantic Tales with a Side of Humor: 5 Fiction Podcasts You Can't Miss – Enjoy romantic stories in podcast form, blending love and laughter. Click here: https://www.thatlovepodcast.com/post/romantic-tales-with-a-side-of-humor-5-fiction-podcasts-you-can-t-miss 

6. Movie Review: Friends with Benefits - A Romantic Comedy That Defies Conventions – Read an insightful review of this modern rom-com. Click here: https://www.thatlovepodcast.com/post/review-of-friends-with-benefits-a-rollicking-rom-com-ride 

7. 10 Unforgettable Meet-Cutes in Romantic Comedy History – Relive iconic first encounters from your favorite rom-coms. Click here: https://www.thatlovepodcast.com/post/10-unforgettable-meet-cutes-in-romantic-comedy-history 

8. Top 10 Romantic Comedy Series to Binge-Watch and Fall in Love With All Over Again – Find your next binge-worthy rom-com series. Click here: https://www.thatlovepodcast.com/post/top-10-romantic-comedy-series-to-binge-watch-and-fall-in-love-with-all-over-again 

9. Movie Review: Crazy, Stupid, Love - A Wildly Romantic Revelation – Delve into a review of this acclaimed romantic comedy. Click here: https://www.thatlovepodcast.com/post/crazy-stupid-love-review-a-wildly-romantic-revelation

10. A Review of the Movie Notting Hill (1999) – Explore an analysis of this classic rom-com. Click here: https://www.thatlovepodcast.com/post/a-review-of-the-movie-notting-hill-1999 

Explore These External Links FOR ANY FILMS INCLUDING ROM COMS!

Rotten Tomatoes

🎥 Your Film Critic HubDive into the world of movie reviews and ratings! With its iconic Tomatometer, Rotten Tomatoes helps you quickly determine if a film is a "fresh" masterpiece or a "rotten" flop.

IMDb

🎬 The Ultimate Entertainment DatabaseThe Internet Movie Database (IMDb) is a treasure trove of information. Discover cast lists, trailers, trivia, and fan reviews for your favorite movies and TV shows.

Metacritic

⭐ Critic Scores at a GlanceMetacritic aggregates reviews from top publications to give you a clear, weighted score—helping you decide if a movie is worth your time.

Letterboxd

📚 Social Networking for CinephilesLog the movies you watch, write reviews, and connect with fellow film enthusiasts. Letterboxd is the ultimate platform for movie buffs to share their passion.

Criticker

🎯 Tailored Film RecommendationsCriticker uses a unique scoring system to suggest movies you'll love, based on your personal ratings and preferences.

MRQE (Movie Review Query Engine)

🔍 The Review AggregatorExplore the web’s largest collection of movie reviews. Search for any title and access critiques from across the internet, all in one place.

Roger Ebert

🎥 The Legacy of a LegendCelebrate the legacy of Roger Ebert. Discover classic reviews, current film critiques, and thought-provoking articles about the deeper meanings of cinema.

Film Comment

🎞️ In-Depth Film AnalysisEnjoy thoughtful analysis and insightful features on the art and craft of filmmaking from one of the most respected film journals.

The Guardian - Film

📰 Latest Film News & ReviewsStay updated with news, reviews, and opinion pieces. The Guardian’s film section offers trusted insights on movies from around the world.

 Enjoyed what you read? Subscribe to That Love Podcast’s newsletter for the latest blogs, updates, and exclusive giveaways! Share the joy—pass along our blogs and website to family and friends so they can join in on the fun. Let’s spread the love together!