Best Romantic Movies To Celebrate Valentine's Day

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The Best 21 Romantic Movies To Watch This Valentine’s Day

“When Harry Met Sally” (1989)

Billy Crystal, Meg Ryan; directed by Rob Reiner

Hailed as the gold standard for the modern romantic comedy, Rob Reiner’s irresistible film is the love story of the high-strung Harry (Billy Crystal) and the levelheaded Sally (Meg Ryan), who have known each other for nearly 12 years. Deep inside, they know there’s a love connection brewing between them, but somehow, they can’t seem to face the music. Do they end up together in the end? Perhaps — but first, brace yourself for the movie’s most iconic scene, the explosively amusing “I’ll have what she’s having” restaurant segment.

“Titanic” (1997)

Leonardo DiCaprio, Kate Winslet; directed by James Cameron

A contemporary depiction of the ill-fated voyage of Titanic, the film is the tragic love story of penniless artist Jack Dawson (Leonardo DiCaprio) and rich girl Rose DeWitt Bukater (Kate Winslet) aboard the massive ship in 1912. The couple’s romance is tragic-yet-captivating to the core.

“Paris Blues” (1961)

Paul Newman, Diahann Carroll, Joanne Woodward, Sidney Poitier; directed by Martin Ritt

Harold Flender’s best-selling novel comes to life in “Paris Blues,” a romantic drama about two itinerant close friends — jazz saxophonist Eddie Cook (Sidney Poitier) and trombone player Ram Bowen (Paul Newman) — who have found that the expatriate life in Paris a breath of fresh air as they experience love and romance with two vacationing American tourists, Connie Lampson (Diahann Carroll) and Lillian Corning (Joanne Woodward) respectively. The whirlwind of their romance is palpable against the backdrop of Parisian bohemia and memorable riffs.

“Past Lives”

Greta Lee, Teo Yoo, John Magaro; directed by Celine Song

Nominated for the 2024 Best Picture Academy Award, “Past Lives” posits a young puppy love suddenly gone adrift in a sea of vagaries. Life marches on, but for one hopeless romantic, time stands still. Greta Lee and Teo Yoo star as two childhood friends who, after two decades, finally get reunited to sort out their feelings and the lingering what-ifs about their “past lives.”

“Love & Basketball” (2000)

Omar Epps, Sanaa Lathan; directed by Gina Prince-Bythewood

Sanaa Lathan and Omar Epps navigate through the complicated-yet-alluring love story of Monica (Lathan) and Quincy (Epps), who first met as children and then became close due to their shared passion for basketball. Can they survive the emotional roller coaster of love — and basketball?

“Casablanca” (1942)

Humphrey Bogart, Ingrid Bergman; directed by Michael Curtiz

A love triangle, an inescapable past, political allegory and wartime passion make “Casablanca” a timeless romantic classic. Winner of Best Picture at the 1944 Academy Awards, it portrays the painful love story of Rick (Humphrey Bogart) and Ilsa (Ingrid Bergman). Together, Bogart’s determined bravado and Bergman’s expressive eyes evoke an unforgettable, palpable chill of sadness in the film’s dramatic ending. Grab those tissues! You will need them, especially when you hear Bogart’s famous lines: “Here’s looking at you, kid” and “We’ll always have Paris.”

“Guess Who’s Coming to Dinner” (1967)

Spencer Tracy, Sidney Poitier, Katharine Hepburn; directed by Stanley Kramer

Over the course of one night, an old couple’s long-held guiding principles are challenged in the face of an intended wedding. Set in 1960s San Francisco, the film stars Spencer Tracy and Katharine Hepburn as Matt and Christina Drayton, an old-line liberal couple who are ill-prepared for their daughter’s shocking big reveal — that is, she is now engaged to John Prentice (Sidney Poitier), a world-renowned African American doctor in the field of tropical medicine. Of course, commotion ensues.

“Ghost” (1990)

Patrick Swayze, Demi Moore, Whoopi Goldberg; directed by Jerry Zucker

“Ghost,” a romantic-fantasy crime thriller, was the movie that undoubtedly made the late Patrick Swayze a love legend. It’s the story of a young woman, Molly Jensen (Demi Moore), and the ghost of her murdered lover, Sam Wheat (Swayze), who tries to warn her of an impending danger with the help of a reluctant psychic (Whoopi Goldberg).

“Crazy Rich Asians” (2018)

Michelle Yeoh, Constance Wu, Henry Golding; directed by Jon M. Chu

Money and class collide with love and romance in “Crazy Rich Asians,” a romantic comedy which centers on New Yorker Rachel Chu (Constance Wu) as she embarks on her first-ever trip to Asia with her longtime boyfriend, Nick Young (Henry Golding). What ensues is a myriad of surprises, jealousy and intrigue, as Rachel discovers that Nick is a member of a Singaporean dynasty. Will their love prevail as the young woman tries to win over Nick’s mom (Michelle Yeoh)?

“It Happened One Night” (1934)

Clark Gable, Claudette Colbert; directed by Frank Capra

The romantic comedy follows socialite Ellie Andrews (Claudette Colbert) who ends up being separated from her husband unwittingly. Over the course of the evening, she tries to get back together with him, but it appears she can only do it with the help of a roguish newspaper reporter (Clark Gable) with whom she eventually falls in love. There’s more to the bland plot than meets the eyes.

“Moonstruck”

Cher, Nicholas Cage; directed by Norman Jewison

In a career-defining moment for Cher, the legendary multi-talented artist won Best Actress in 1988 at the 60th Academy Awards for her portrayal of a widower who suddenly falls for her future brother-in-law (Nicholas Cage). This rom-com celebrates love with profound passion and tenderness.

“Love Story” (1970)

Ali MacGraw, Ryan O’Neal; directed by Arthur Hiller

A film adaptation of Erich Segal’s best-selling novel, the romantic drama is about two college students who fall in love and build a life together despite the objections of their families. Ryan O’Neal and Ali MacGraw portray the young lovers who get separated in the end. Get ready to be moved to tears!

“The Shape of Water” (2017)

Octavia Spencer, Sally Hawkins; directed by Guillermo del Toro

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Best Picture winner at the 2018 Academy Awards, Guillermo del Toro’s other-worldly fairytale follows Elisa (Hawkins), a cleaning lady in a high-tech U.S. government laboratory, who accidentally discovers a monster being held captive in the top-secret facility. As the mute young woman befriends the fascinating creature, their emotional bond deepens and leads to an unlikely romance. “The Shape of Water” is the first-ever sci-fi film to win Oscar’s most coveted top prize.

“Breakfast at Tiffany’s” (1961)

Audrey Hepburn, George Peppard; directed by Blake Edwards

Sentiment and cynicism are in perfect balance in this endearing classic about two lost souls. Audrey Hepburn plays free-spirited Holly Golightly, while George Peppard plays sensitive Paul Varjak. Ultimately, both find love and redemption in each other’s arms. The romance has elegance, style, color and humor. The famous Givenchy-designed black dress that Hepburn wore in the film was auctioned off at Christie’s for more than $900,000 in 2006.

“The Notebook” (2004)

Ryan Gosling, Rachel McAdams; directed by Nick Cassavetes

A film adaptation of Nicholas Sparks’ best-selling novel of the same name, “The Notebook” is a romantic drama that chronicles the love affair of mill worker Noah Calhoun (Ryan Gosling) and rich girl Allie (Rachel McAdams) in 1940s South Carolina. Their past lives are shown through a series of flashbacks as Noah tirelessly reminds Allie about their undying love for each other despite her Alzheimer’s disease.

“The Lady Eve” (1941)

Barbara Stanwyck, Henry Fonda; directed by Preston Sturges

In this screwball masterpiece, Barbara Stanwyck plays Jean Harrington, a con woman who targets Charles Pike (Henry Fonda), heir to a brewery fortune. A seductress taming a naive innocent man sounds simple enough for a plot? Not really. Complications ensue as she falls for him — for real.

“Pretty Woman” (1990)

Richard Gere, Julia Roberts; directed by Garry Marshall

It’s the Cinderella story of wealthy businessman Edward Lewis (Richard Gere) falling for prostitute Vivian (Julia Roberts), who is struggling with her lifestyle. The heart and soul of the movie lies in the charismatic chemistry of the two leads.

“Dirty Dancing” (1987)

Patrick Swayze, Jennifer Grey; directed by Emile Ardolino

Set in the summer of 1963, this semi-musical is the story of a self-conscious young girl, Frances “Baby” Houseman (Jennifer Grey), who finds courage and first love in the arms of dance instructor Johnny Castle (Patrick Swayze). The movie’s box office success spawned one of the best-selling soundtrack albums of all time, unleashing the emotional power of mambos and cha-cha-chas to wider mainstream.

“Gone with the Wind” (1939)

Clark Gable, Vivien Leigh; directed by Victor Fleming

A film adaptation of Margaret Mitchell’s Pulitzer Prize-winning novel of the same name, “Gone with the Wind” is a classic tale of a love-hate romance. The Civil War period drama narrates the story of peevish Southern belle Scarlett O’Hara (Vivien Leigh), tracing her survival through the tragic history of the South during the American Civil War, her love affair with Rhett Butler (Clark Gable), and finally her understanding of life and love.

“Carrie Pilby” (2016)

Bel Powley, Nathan Lane; directed by Susan Johnson

Caren Lissner’s 2003 best-seller comes to life in Susan Johnson’s romantic comedy about 19-year-old Carrie Pilby, a recent Harvard graduate struggling to find her place in the world because of her overactive moral compass. Bel Powley shines as the genius title character who must ultimately give humanity a chance to find happiness — and even romance.

“Annie Hall” (1977)

Woody Allen, Diane Keaton; directed by Woody Allen

The movie follows the story of comedian Alvy Singer (Woody Allen) and his relationship with struggling nightclub singer Annie Hall (Diane Keaton), focusing mainly on the highs and lows of their love affair. As Woody Allen’s signature film, expect it to gravitate in a whirlwind fashion of unbridled cleverness and hilarity.

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