The 50+ Best Movies About Unrequited Love, Ranked
- 1Joseph Gordon-Levitt, Zooey Deschanel, Geoffrey Arend
This quirky romantic comedy-drama features Joseph Gordon-Levitt as Tom Hansen, an aspiring architect turned greeting card writer who falls for his co-worker Summer Finn (played by Zooey Deschanel). Narrated through a non-linear timeline, we witness their relationship unfold and ultimately crumble as Tom accepts the reality that Summer does not share his feelings. The film poignantly captures the complexities of modern relationships and unrequited love.
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- 2Molly Ringwald, Jon Cryer, Andrew McCarthy
Another John Hughes classic, this 80s teen drama follows Andie Walsh (Molly Ringwald), a working-class girl who falls for wealthy Blane McDonough (Andrew McCarthy). Simultaneously, Duckie Dale (Jon Cryer), Andie's quirky best friend, harbors secret feelings for her but struggles with expressing his emotions. The film poignantly explores themes of social status and unrequited love through these complex relationships.
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- 3Julia Roberts, Dermot Mulroney, Cameron Diaz
This romantic comedy stars Julia Roberts as Julianne Potter, a woman who realizes she is in love with her best friend Michael O'Neal (Dermot Mulroney) just days before his wedding to another woman. Desperate to win him back, Julianne devises schemes to sabotage the wedding – leading to hilarious antics and an exploration of what it means to truly love someone.
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- 4Humphrey Bogart, Ingrid Bergman, Paul Henreid
Set during World War II, this classic film tells the story of Rick Blaine (Humphrey Bogart), a nightclub owner in Casablanca who encounters his former lover Ilsa Lund (Ingrid Bergman) and her husband Victor Laszlo (Paul Henreid). Torn between his feelings for Ilsa and his loyalty towards Victor, Rick must make a difficult decision that will forever impact their lives – emphasizing the sacrifices one makes for unrequited love.
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- 5Leonardo DiCaprio, Tobey Maguire, Carey Mulligan
Based on F. Scott Fitzgerald's novel, this lavish film adaptation directed by Baz Luhrmann stars Leonardo DiCaprio as Jay Gatsby, a mysterious millionaire who throws extravagant parties in hopes of winning back his lost love Daisy Buchanan (Carey Mulligan). Despite his efforts to convince her to leave her husband, Tom (Joel Edgerton), Gatsby's dream ultimately remains unfulfilled – illustrating the futility of chasing an idealized past.
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- 6Johnny Depp, Winona Ryder, Dianne Wiest
In Tim Burton's dark fairy tale, Johnny Depp stars as Edward Scissorhands, a gentle yet misunderstood being with scissors for hands who falls in love with Kim Boggs (Winona Ryder). Despite their deep connection, society's prejudice against Edward forces them apart – highlighting the bittersweet nature of unrequited love amidst societal judgment.
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- 7Tom Hanks, Robin Wright, Gary Sinise
This iconic film stars Tom Hanks as the lovable, simple-minded Forrest Gump who falls in love with his childhood friend Jenny (played by Robin Wright). Throughout the movie, their lives intersect at various points, but Jenny's personal struggles and emotional turmoil prevent her from reciprocating Forrest's unwavering devotion. The theme of unrequited love is a central aspect of this classic tale that explores the power of friendship, perseverance, and the human spirit.
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- 8Logan Lerman, Emma Watson, Ezra Miller
Based on Stephen Chbosky's novel, this coming-of-age drama chronicles introverted Charlie Kelmeckis' (Logan Lerman) freshman year of high school as he befriends free-spirited Sam (Emma Watson) and her stepbrother Patrick (Ezra Miller). As Charlie navigates adolescence, he develops feelings for Sam but struggles to express his love due to their deep friendship – ultimately exploring the pain of unrequited affection.
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- 9Ryan Gosling, Rachel McAdams, James Garner
Based on Nicholas Sparks' best-selling novel, this romantic drama tells the story of young lovers Allie Hamilton (Rachel McAdams) and Noah Calhoun (Ryan Gosling), whose passionate romance faces numerous obstacles due to societal expectations and differing backgrounds. Despite their deep connection, they are separated for years before reuniting when it is too late – Allie is engaged to another man, leading to an achingly poignant portrayal of unfulfilled love.
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- 10Jim Carrey, Kate Winslet, Kirsten Dunst
Eternal Sunshine of the Spotless Mind: In this unique sci-fi romance directed by Michel Gondry, Joel Barish (Jim Carrey) undergoes a procedure to erase all memories of his tumultuous relationship with Clementine Kruczynski (Kate Winslet). However, as Joel relives their time together during the process, he begins to question whether erasing their past is truly worth losing the lessons learned from heartbreak.
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- 11Molly Ringwald, Anthony Michael Hall, Michael Schoeffling
In this quintessential 80s teen flick directed by John Hughes, Samantha Baker (Molly Ringwald) deals with her crush on popular jock Jake Ryan (Michael Schoeffling), while also navigating family drama surrounding her forgotten birthday. As she yearns for Jake's attention throughout the movie, Samantha experiences the heartache associated with unrequited teenage infatuation.
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- 12Cameron Diaz, Kate Winslet, Jude Law
In this romantic comedy, two women – Iris Simpkins (Kate Winslet) and Amanda Woods (Cameron Diaz) – swap homes for the holidays to escape their respective romantic troubles. While navigating new surroundings, they each find unexpected connections with local men, yet still grapple with unresolved feelings from past relationships. The film thoughtfully explores themes of healing from heartbreak and moving forward after experiencing unrequited love.
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- 13Cary Elwes, Robin Wright, Mandy Patinkin
This beloved fairy tale film directed by Rob Reiner features the love story of Westley (Cary Elwes) and Princess Buttercup (Robin Wright). Although they are deeply in love, circumstances force them apart, and Buttercup becomes engaged to the evil Prince Humperdinck. Throughout their journey filled with adventure and danger, Westley's unwavering devotion to Buttercup is a testament to the power of true love.
- 14Leonardo DiCaprio, Kate Winslet, Billy Zane
James Cameron's epic romantic disaster film showcases the tragic love story between Jack Dawson (Leonardo DiCaprio), a poor artist, and Rose DeWitt Bukater (Kate Winslet), an aristocrat on board the ill-fated RMS Titanic. Their passionate affair is cut short due to class differences and the ship's sinking – ultimately leaving their love unfulfilled.
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- 15Daniel Day-Lewis, Madeleine Stowe, Russell Means
Set during the French and Indian War, this historical epic follows Hawkeye (Daniel Day-Lewis), a white man raised by Native Americans, as he falls for Cora Munro (Madeleine Stowe), the daughter of a British officer.Their passionate romance faces numerous challenges due to the ongoing conflict and cultural differences. The film's portrayal of unrequited love highlights the power of devotion amidst adversity and the sacrifices one must make for their beloved.
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- 16Nicolas Cage, Meg Ryan, Andre Braugher
This romantic fantasy drama features Nicolas Cage as Seth, an angel who becomes infatuated with human surgeon Maggie Rice (Meg Ryan) after witnessing her grief over losing a patient. As Seth grapples with his newfound emotions and desires to become mortal for Maggie, he faces the harsh reality that their love may never be fully realized due to their contrasting existences.
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- 17Natalie Wood, Richard Beymer, Russ Tamblyn
Inspired by Shakespeare's Romeo and Juliet, this classic musical explores the tragic love story between Tony (Richard Beymer) and Maria (Natalie Wood), members of rival New York City gangs. Their forbidden romance highlights the power of love amidst adversity but also showcases its devastating consequences when left unfulfilled.
- 18Patrick Swayze, Demi Moore, Whoopi Goldberg
This supernatural romance stars Patrick Swayze as Sam Wheat, a murdered man who returns as a ghost to protect his lover Molly Jensen (Demi Moore) from impending danger. Despite being unable to touch or communicate with her directly, Sam's spirit remains devoted to Molly throughout the movie – illustrating the lengths one will go for unrequited love.
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- 19Madeline Carroll, Callan McAuliffe, Rebecca De Mornay
This coming-of-age romantic comedy follows Juli Baker (Madeline Carroll) and Bryce Loski (Callan McAuliffe) as they navigate the trials and tribulations of adolescence while dealing with their conflicting feelings towards each other. As Juli's infatuation with Bryce evolves into genuine love, she must confront the reality that her feelings may never be reciprocated – capturing the essence of unrequited teenage affection.
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- 20Cary Grant, Deborah Kerr, Richard Denning
Starring Cary Grant as playboy Nickie Ferrante and Deborah Kerr as singer Terry McKay, this classic romance tells the story of two strangers who fall in love aboard a cruise ship despite being engaged to others. They agree to meet six months later at the top of the Empire State Building, but fate intervenes – leaving them wondering if their love will ever come to fruition.
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- 21Robin Williams, Cuba Gooding, Annabella Sciorra
In this visually stunning fantasy drama, Robin Williams stars as Chris Nielsen, a man who dies in a car accident and ventures through the afterlife in search of his wife Annie (Annabella Sciorra) who commits suicide following his death. As he navigates the realms of Heaven and Hell to reunite with her, their love endures despite seemingly insurmountable obstacles.
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- 22Leonard Whiting, Olivia Hussey, Milo O'Shea
William Shakespeare's timeless tragedy has been adapted countless times on screen, notably in Baz Luhrmann's 1996 modernized version starring Leonardo DiCaprio as Romeo Montague and Claire Danes as Juliet Capulet. The story of their forbidden love and the consequences it bears for both their feuding families remains a poignant reminder of the pain and devastation unrequited love can bring.
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- 23Heath Ledger, Jake Gyllenhaal, Linda Cardellini
Ang Lee's groundbreaking film follows two cowboys, Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal), whose passionate affair spans decades despite both men marrying women and leading seemingly heterosexual lives. Their secret relationship is fraught with longing and heartbreak as they struggle to reconcile their true desires with societal expectations.
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- 24Ben Affleck, Jennifer Aniston, Drew Barrymore
Adapted from Greg Behrendt's self-help book, this ensemble romantic comedy-drama follows various characters as they navigate complex relationships and miscommunications in modern dating culture. Throughout multiple storylines, we witness different forms of unrequited love – whether it be through one-sided crushes or failed attempts at rekindling past flames – offering a relatable and poignant exploration of the topic.
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- 25Bill Murray, Scarlett Johansson, Giovanni Ribisi
Sofia Coppola's critically acclaimed film stars Bill Murray as aging actor Bob Harris and Scarlett Johansson as college graduate Charlotte, both feeling lost and disconnected during a trip to Tokyo. As they form a bond over shared experiences and loneliness, their connection remains platonic yet deeply emotional – illustrating the complexities of unrequited love in unexpected circumstances.
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- 26Clint Eastwood, Meryl Streep, Annie Corley
Adapted from Robert James Waller's novel, this romantic drama stars Meryl Streep as Francesca Johnson, an Italian war bride living in Iowa who falls for National Geographic photographer Robert Kincaid (Clint Eastwood). Their brief yet intense love affair is marked by deep longing and unfulfilled desires as they grapple with the consequences of their actions on their respective families.
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- 27Christopher Reeve, Jane Seymour, Christopher PlummerSomewhere in Time is a romantic drama that sees Richard Collier (Christopher Reeve), a play writer, become smitten by a photo of Elise McKenna (Jane Seymour), an actress from the early 1900s. In his quest for love, Richard employs self-hypnosis to time travel back to 1912. Intriguingly, he succeeds and meets Elise, leading to a passionate romance. This film, directed by Jeannot Szwarc and based on the novel Bid Time Return by Richard Matheson, captivates with its blend of love across time, mystery, and the power of one's mind.More Somewhere in Time
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- 28Ryan Gosling, Emma Stone, John Legend
This critically acclaimed musical stars Ryan Gosling as aspiring jazz musician Sebastian Wilder and Emma Stone as aspiring actress Mia Dolan, who fall in love while pursuing their dreams in Los Angeles. As they face the harsh realities of balancing ambition with personal relationships, their romance ultimately ends – showcasing the bittersweet nature of unrequited love when ambitions take precedence over emotional connections.
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- 29Audrey Tautou, Mathieu Kassovitz, Rufus"Amélie" is a fanciful comedy about a young woman who discretely orchestrates the lives of the people around her, creating a world exclusively of her own making. Shot in over 80 Parisian locations, acclaimed director Jean-Pierre Jeunet ("Delicatessen"; "The City of Lost Children") invokes his incomparable visionary style to capture the exquisite charm and mystery of modern-day Paris through the eyes of a beautiful ingenue.More Amélie
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- 30Greta Lee, Teo Yoo, John MagaroNora and Hae Sung, two deeply connected childhood friends, are wrest apart after Nora's family emigrates from South Korea. Decades later, they are reunited for one fateful week as they confront destiny, love and the choices that make a life.More Past Lives
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