30 Best Valentine’s Day Movies: From Hopeless Romantics to Holiday Haters

Love is in the air, and what better way to celebrate Valentine’s Day than with a cozy movie night? Whether you’re cuddled up with your significant other or enjoying some solo self-love, we’ve curated a list of the 30 Best Valentine’s Day Movies to set the mood just right. From timeless classics to modern rom-coms, there’s something for everyone to enjoy on this special day of love. So grab some popcorn, dim the lights, and let the magic of cinema sweep you off your feet.

30. The Twilight Saga, 2008

And our Best Valentine’s Day Movies compilation opens with a new classic. The Twilight Saga presents a captivating blend of romance and fantasy, making it an ideal choice for Valentine’s Day viewing. Follow Bella and Edward’s epic love story amidst the backdrop of supernatural intrigue. With its passionate performances and mesmerizing visuals, it’s sure to enchant audiences seeking a tale of eternal love.

29. 50 First Dates, 2004

In 50 First Dates Henry Roth, played by Adam Sandler, faces the challenge of dating Lucy Whitmore, played by Drew Barrymore, who suffers from short-term memory loss. Despite the heartbreak, Henry’s relentless efforts to recreate their initial romance are both touching and inspiring, making it impossible not to be moved by his determination.

28. When We First Met, 2018

When We First Met offers a fresh take on the rom-com genre with its time-traveling twist. Adam Devine’s character, Noah, gets the chance to relive the night he first met his crush, Avery, Alexandra Daddario, hoping to change their relationship’s trajectory. With humor and heart, it’s a charming choice for watching with your loved one.

27. Never Been Kissed, 1999

Never Been Kissed follows Josie Geller, Drew Barrymore, a journalist who goes undercover as a high school student to research a story. As she navigates the complexities of adolescence, Josie discovers love and friendship while confronting her own insecurities. With its blend of humor and heartfelt moments, this film is a nostalgic and endearing choice.

26. Just Wright, 2010

In the romantic comedy Just Wright, physical therapist Leslie Wright, played by Queen Latifah, develops feelings for her patient, NBA star Scott McKnight, played by Common. Despite Scott’s attraction to Leslie’s friend Morgan, you will find yourself rooting for Leslie as she pursues her chance at love with him.

25. 13 Going on 30, 2004

13 Going on 30 follows Jenna Rink, Jennifer Garner, who magically transforms from a 13-year-old girl to a 30-year-old woman overnight. As she navigates adulthood with a childlike innocence, Jenna rediscovers the importance of friendship and staying true to oneself. With its blend of humor and heart, this film is a delightful choice for Valentine’s Day.

24. One Day, 2011

One Day, starring Anne Hathaway and Jim Sturgess, is a poignant tale of love and friendship spanning two decades. The film follows Dexter and Emma, who reunite on July 15th each year to reflect on their evolving relationship. Hathaway’s performance shines in this emotionally resonant story, perfect for a heartfelt evening.

23. Sylvie’s Love, 2020

In Sylvie’s Love the allure isn’t just the captivating love story but also the stunning depiction of 1950s and 1960s New York through exquisite sets and costumes. Tessa Thompson portrays Sylvie, an aspiring TV producer drawn to jazz musician Robert, played by Nnamdi Asomugha. Despite their initial obstacles, fate grants them a second chance at love years later.

22. Blue Valentine, 2010

Blue Valentine is a raw and emotionally intense exploration of love’s complexities. Ryan Gosling and Michelle Williams deliver powerful performances as a couple whose relationship unravels over time. Through non-linear storytelling, the film poignantly captures both the joy and heartbreak of romance, leaving a lasting impact on audiences.

21. Portrait of a Lady on Fire, 2019

For those seeking a deeply emotional experience, this French film delivers. Marianne, an artist, played by Noémie Merlant, is tasked with painting Héloïse, played by Adèle Haenel, a soon-to-be-married aristocrat. As their forbidden love blossoms, their affair profoundly alters both their lives in this heart-wrenching tale.

20. She’s the Man, 2006

The top 20 of Best Valentine’s Day Movies compilation opens with a film that became one of the most iconic rom-com of two thousandth. She’s the Man is a hilarious modern twist on Shakespeare’s “Twelfth Night.” Amanda Bynes shines as Viola, who disguises herself as her twin brother to join a soccer team and win over her crush. With its comedic charm and romantic escapades, it’s a fun choice for Valentine’s Day entertainment.

19. Maid in Manhattan, 2002

Consider this ’00s rom-com gem for a heartwarming Cinderella-esque tale. Jennifer Lopez portrays Marisa, a single mother employed at a luxurious NYC hotel. A chance encounter with Chris, Ralph Fiennes, a senatorial candidate, sparks a romance, but can they navigate their differences? You’ll adore the chemistry, especially the charming scenes featuring Marisa’s 10-year-old son, played by the talented young Tyler Posey.

18. Lady Chatterley’s Lover, 2022

D.H. Lawrence’s controversial 1929 novel, once banned in the United States for its explicit language, receives a sumptuous adaptation in Laure de Clermont-Tonnerre’s romantic drama. Emma Corrin portrays Lady Constance Chatterley, married to a paralyzed aristocrat. Her affair with the estate’s gamekeeper, played by Jack O’Connell, ignites a passionate awakening to her desires and aspirations.

17. The Bodyguard, 1992

The Bodyguard is a timeless romantic thriller that captivates audiences with its gripping storyline and unforgettable performances. Kevin Costner stars as a former Secret Service agent hired to protect Whitney Houston’s character, a famous singer stalked by a dangerous stalker. Their on-screen chemistry, coupled with iconic songs like “I Will Always Love You,” makes this film an enduring classic.

16. 10 Things I Hate About You, 1999

Watching this teen adaptation of Shakespeare’s “The Taming of the Shrew,” you’ll undoubtedly reminisce about the late Heath Ledger. His chemistry with Julia Stiles, who plays Kat, is a highlight as they portray the characters Patrick and Kat. Stiles’s emotional speech professing both love and hate for Ledger’s bad-boy role is particularly riveting.

15. Always Be My Maybe, 2019

In this delightful Netflix rom-com, Ali Wong and Randall Park portray childhood friends with unresolved feelings. When Sasha, Wong, returns to San Francisco, she reconnects with Marcus, Park, now a struggling musician. Can they overcome their divergent paths—her as a renowned chef and him still living at home? Plus, Keanu Reeves makes a memorable cameo appearance.

14. Crazy, Stupid, Love, 2011

Crazy, Stupid, Love is a witty and heartfelt romantic comedy that navigates the complexities of relationships with humor and charm. Steve Carell shines as a newly single man navigating the dating world with the help of Ryan Gosling’s suave mentorship. With a stellar ensemble cast and clever plot twists, this film delivers laughs and genuine emotional depth, making it a standout in the genre.

13. Eternal Sunshine of the Spotless Mind, 2004

Eternal Sunshine of the Spotless Mind is a mesmerizing blend of sci-fi and romance that explores the complexities of love and memory. Jim Carrey and Kate Winslet deliver captivating performances as Joel and Clementine, a couple who undergo a procedure to erase each other from their memories. As their memories unravel, the film poignantly delves into the beauty and pain of relationships, leaving a lasting impression on viewers. With its inventive storytelling and emotional depth, it’s a must-watch for anyone seeking a thought-provoking and unforgettable cinematic experience.

12. Pretty Woman, 1990

Pretty Woma remains an iconic romantic comedy that has captivated audiences for decades. Julia Roberts shines as Vivian, a spirited prostitute, while Richard Gere charms as Edward, a wealthy businessman. Their unlikely love story unfolds against the backdrop of Beverly Hills, filled with humor, heart, and memorable moments. With its timeless appeal and irresistible chemistry between the leads, Pretty Woman continues to be a beloved classic that enchants viewers of all generations.

11. Bridget Jones’s Diary, 2001

Bridget Jones’s Diary is a delightful romantic comedy that follows the quirky and endearing Bridget, Renée Zellweger, as she navigates the ups and downs of love, life, and self-discovery. With its witty humor, relatable characters, and charming British setting, the film offers a heartwarming and entertaining portrayal of one woman’s journey towards finding happiness and acceptance.

Renée Zellweger’s portrayal of Bridget is both comedic and touching, making her an unforgettable character in the realm of romantic comedies. Whether you’re a fan of the original novel or discovering the story for the first time, Bridget Jones’s Diary is a delightful film that will leave you laughing, crying, and cheering for Bridget every step of the way.

10. Flipped, 2010

The top 10 of Best Valentine’s Day Movies opens Flipped is a charming coming-of-age story that beautifully captures the innocence and complexities of first love. Directed by Rob Reiner, the film follows the evolving relationship between Juli and Bryce, portrayed by Madeline Carroll and Callan McAuliffe, as they navigate childhood and adolescence in the 1960s. Set against the backdrop of a suburban neighborhood, Flipped is a nostalgic journey filled with heartwarming moments, poignant reflections, and relatable characters.

The film explores themes of friendship, family, and the power of perspective, offering a refreshing take on the classic romantic comedy genre. With its authentic performances and heartfelt storytelling, Flipped is a touching and memorable film that resonates with audiences of all ages.

9. Before Film Trilogy, 1995

The Before trilogy, comprising “Before Sunrise,” “Before Sunset,” and “Before Midnight,” is a masterful exploration of love, time, and human connection. Directed by Richard Linklater and starring Ethan Hawke and Julie Delpy, each film follows the evolving relationship between Jesse and Céline over the course of several years.

In Before Sunrise, the duo meets on a train and shares a spontaneous, romantic night wandering through Vienna. Before Sunset reunites them nine years later in Paris, where they confront the consequences of their choices and the passage of time. Finally, Before Midnight delves into the complexities of their long-term relationship as they navigate the challenges of parenthood and commitment.

What sets the trilogy apart is its naturalistic dialogue and intimate storytelling, allowing viewers to witness the profound emotional connection between Jesse and Céline as they grapple with life’s uncertainties and their own personal growth. Each film is a gem in its own right, but together they form a deeply moving and thought-provoking exploration of love and human connection that lingers long after the credits roll.

8. Valentine’s Day, 2010

The 2010 film Valentine’s Day boasts an ensemble cast featuring Hollywood A-listers like Julia Roberts, Jessica Alba, Jessica Biel, Jamie Foxx, Anne Hathaway, Bradley Cooper, and even Taylor Swift. With intertwining storylines, the movie offers a captivating glimpse into the interconnected lives of its diverse characters.

7. The Notebook, 2004

The Notebook is a timeless romantic drama that tugs at the heartstrings. Ryan Gosling and Rachel McAdams deliver unforgettable performances as Noah and Allie, whose epic love story spans decades. With its emotional depth and poignant moments, it’s a perfect choice for a Valentine’s Day viewing that will leave you reaching for the tissues.

6. Mamma Mia!, 2008

Mamma Mia! is a feel-good musical extravaganza perfect for Valentine’s Day. Set on a picturesque Greek island, this film follows bride-to-be Sophie, Amanda Seyfried, as she tries to uncover the identity of her father before her wedding. With the help of her mother’s, Meryl Streep, former bandmates (Pierce Brosnan, Colin Firth, and Stellan Skarsgård), the stage is set for a joyous celebration filled with ABBA’s timeless hits and heartwarming moments.

5. Brokeback Mountain, 2005

For those drawn to poignant romances with emotional depth, Brokeback Mountain is a must-watch. Set against the backdrop of 1960s Wyoming, the film chronicles the clandestine love affair between two cowboys, who grapple with societal expectations and personal desires. Winner of three Academy Awards, including Best Director for Ang Lee, it’s a powerful portrayal of love, longing, and sacrifice.

4. Dirty Dancing, 1987

Dirty Dancing ignites passion with its rebellious charm. Patrick Swayze’s Johnny Castle defies convention, standing up to Baby’s father in a dance-filled summer fling. Jennifer Grey’s Baby finds love and self-discovery amidst soulful music and electrifying dance routines. Set against a backdrop of forbidden romance, the film delivers sizzling chemistry and unforgettable moments. Get ready for a captivating journey through love, music, and dance.

3. Roman Holiday, 1953

Audrey Hepburn’s iconic performance in Breakfast at Tiffany’s may have been legendary, but William Wyler’s Roman Holiday made lunch, dinner, and Vespa rides in Rome an unforgettable cultural experience. This Oscar-winning film sparked a trend of American movies set in Rome, yet its heart lies in its enchanting romance. Let’s delve into the timeless allure of love amidst the beauty of Rome.

2. Titanic, 1997

Titanic is a timeless epic that transcends generations. Leonardo DiCaprio and Kate Winslet’s unforgettable performances as Jack and Rose bring to life the tragic yet captivating love story aboard the ill-fated ship. With stunning visuals, heart-wrenching moments, and a powerful soundtrack, this film is a perfect choice for Valentine’s Day. Get ready to embark on an emotional journey that will leave you breathless and reaching for your loved one’s hand.

1. Casablanca, 1942

The leader of our compilation Best Valentine’s Day Movies becomes Casablanca. This film remains a cinematic masterpiece and a timeless classic. Set against the backdrop of World War II, Humphrey Bogart’s portrayal of Rick Blaine and Ingrid Bergman’s luminous presence as Ilsa Lund create an unforgettable love story. With its iconic dialogue, unforgettable characters, and poignant themes of sacrifice and redemption, Casablanca continues to enchant audiences around the world, making it a must-watch for cinephiles of all ages.

Before you go, read another article about 20 Best Shows on HBO Max of All Time, Ranked.