Love is in the Air (and on Your Screen): Valentine's Day (2025) Movie Picks for Everyone

Valentine's Day is here, and whether you're planning a cozy night in with your sweetheart or embracing the single life, there's a perfect movie out there to set the mood. I've compiled a list of classic and contemporary films to suit every taste, from heartwarming romances to laugh-out-loud comedies and everything in between. So grab your popcorn, dim the lights, and get ready to press play!

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Links to movie titles are to the Prime Video (or DVD, if not available on Prime Video) version on Amazon.

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Valentine's Day Movie Classics (and Some Newer Gems)

This list spans the decades, offering a mix of iconic love stories and modern favorites that capture the spirit of Valentine's Day:

• 1920s: The Sheik (1921) - A silent film classic featuring Rudolph Valentino, perfect for a taste of old Hollywood romance. Free: Prime Video/Freevee, Plex.
• 1930s: It Happened One Night (1934) - A delightful screwball comedy with witty banter and undeniable chemistry.
• 1940s: Casablanca (1942) - A timeless tale of love and sacrifice set against the backdrop of World War II. Subscription: Max.
• 1950s: Roman Holiday (1953) - A charming story about a princess who finds love and adventure in Rome.
• 1970s: Annie Hall (1977) - A groundbreaking romantic comedy-drama that explores the complexities of relationships.
• 1980s: When Harry Met Sally... (1989) - A beloved classic that questions whether men and women can ever truly be just friends. Subscription: Max.
• 1990s: Sleepless in Seattle (1993) - A heartwarming story about destiny and second chances.
• 2000s: Love Actually (2003) - A feel-good ensemble rom-com with interwoven stories of love and connection. Subscription: Peacock.
• 2010s: Crazy Rich Asians (2018) - A contemporary romantic comedy with a lavish setting and a focus on family and cultural identity. Subscription: Max.
• 2020s: Palm Springs (2020) - A clever and original take on the time-loop romantic comedy genre. Subscription: Hulu.

Anti-Valentine's Day Movies (for the Cynics and the Single & Free)

Not in the mood for hearts and flowers? These movies offer a different perspective on love and relationships:

• Eternal Sunshine of the Spotless Mind (2004) - A thought-provoking film about heartbreak and the desire to forget. Subscription: Peacock.
• 500 Days of Summer (2009) - A non-traditional romantic comedy that deconstructs the typical love story.
• Gone Girl (2014) - A dark and twisty thriller that explores the complexities of marriage.

Perfect for a Solo Night In

These movies are perfect for those who want to enjoy a relaxing and entertaining evening alone:

• Chef (2014) - A feel-good movie about food, family, and starting over. Subscription: Max.
• Singin' in the Rain (1952) - A classic musical filled with joy and optimism. Subscription: Max.
• The Princess Bride (1987) - A timeless fairy tale with action, romance, and humor. Subscription: Disney Plus.

Cozy Up Together: Movies for Couples

These movies are perfect for sharing with your special someone:

• The Notebook (2004) - A tearjerker romance that spans decades. Subscription: Max.
• La La Land (2016) - A visually stunning musical about dreams and love. Subscription: Netflix.
• Pride & Prejudice (2005) - A classic period drama with witty dialogue and undeniable romance.

Something Different: A Star is Born - Four Versions, Four Eras

For a unique Valentine's Day movie experience, why not explore the different versions of A Star is Born? This classic tale of love, loss, and the pursuit of dreams has been remade four times, each offering a distinct perspective on the timeless story.

• 1937: The original, starring Janet Gaynor and Fredric March, is a classic Hollywood melodrama. Subscription: Max.
• 1954: The Judy Garland and James Mason version is a musical masterpiece. Subscription: Max.
• 1976: The Barbra Streisand and Kris Kristofferson version is a rock-and-roll spectacle.
• 2018: The Lady Gaga and Bradley Cooper version is a modern take on the classic. Subscription: Hulu.

Watching these films together (or solo!) can spark fascinating conversations about how storytelling and filmmaking have evolved over time, while still exploring the core themes of love, ambition, and sacrifice.

A Word of Caution: While "A Star is Born" offers a powerful and passionate love story, it's important to note that all versions of the film also contain tragic elements. The story explores themes of addiction, career decline, and ultimately, loss. If you're looking for a purely lighthearted and feel-good Valentine's Day movie, "A Star is Born" might not be the best choice. However, if you appreciate films that delve into the complexities of love and relationships, and if you're prepared for a potentially emotional experience, then exploring the different versions of this classic tale could be a unique and rewarding way to spend Valentine's Day.

No matter what your plans are for Valentine's Day, there's a movie out there that's perfect for you. So curl up on the couch, grab your favorite snacks, and enjoy!

My Streaming Life is all about finding the perfect content to stream, and these Valentine's Day movie suggestions should give you a great start to planning your viewing.