Dating all the way back to ancient greek tragedy and even earlier, unrequited love is a common figure of speech in Hollywood and has been portrayed in countless films over time, with varying degrees of longevity and success. A one-sided love story has the power to move and touch the audience, as their fate often endears, frustrates and amuses the masses. This style of storytelling is no stranger to the silver screen, with some of the most memorable and iconic films applying this heartbreaking, tear-jerking concept to more effect than others.
Updated September 23, 2022: If you’re a fan of the unrequited love trope, you’ll be happy to hear that this article has been updated with additional content and movies.
Whether it’s the all-consuming love of a literary great, the misguided attempts of a hopeless romantic, or the desperate longing for an unattainable crush, stories of unrequited love have always found a permanent home in Tinsel Town. Real love may not be like movie lovebut since so many people experience the highs and lows of romance, let’s take a look at some of the best unrequited love movies.
12 Ghost world
MGM
Terry Zwigoff’s critically acclaimed dark comedy Ghost world revolves around the lives of Enid and Rebecca, two teenage outsiders whose once-close friendship becomes strained when Enid takes an interest in an older man’s love life. With the talented Thora Birch and Scarlett Johansson as the duo and Steve Buscemi as a lonely middle-aged record collector, Ghost world is based on the Daniel Clowes comic book of the same name. Enid makes it her mission to help the reclusive Seymour find a wife, while developing a crush on the older man. While it’s not really a typical Valentine’s Day staple, Ghost world takes the audience on a journey of self-examination and perfectly portrays the pain of adolescents.
11 Love actually
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One of the most iconic film depictions of unrequited love, 2003 Love actually follows the lives of eight completely different couples a month before Christmas as their stories unintentionally intertwine. Mark (Andrew Lincoln) is hopelessly in love with his best friend’s new bride, Juliet (Kiera Knightley), and in his efforts to hide his feelings, he comes across as indifferent and seemingly cool to her. When Juliet tries to smooth out their relationship, Mark is inspired to declare his love for her via a boombox and large cue cards. Love actually has become a modern Christmas classic and perfectly captures the heartbreaking reality of unrequited love.
10 Welcome to the dollhouse
Todd Solondz’s brutal 1995 coming-of-age comedy Welcome to the dollhouse tells the story of bullied and unpopular 11-year-old Dawn Wiener, a shy girl who feels constantly overlooked by her family and friends and desperately tries to stand out and get their attention. When her geeky older brother forms a band and hunky new student Steve Rodgers joins them, Dawn is absolutely in love with the high school student, despite everyone telling her she doesn’t stand a chance with the musician. The acclaimed independent film showcases Dawn’s growing obsession with Steve and chronicles the embarrassing highs and lows of adolescent crushes and unrequited romantic feelings that run rampant in childhood.
9 The Great Gatsby
Baz Luhrmann’s maximalist adaptation of F. Scott Fitzgerald’s beloved novel The Great Gatsby tells the story of millionaire Jay Gatsby as he meets his neighbor Nick Carraway and yearns for his former love Daisy Buchanan during the Roaring Twenties. Leonardo DiCaprio and Carey Mulligan play the ill-fated lovers, while Tobey Maguire stars as aspiring writer Nick. The heartbreaking love affair between Jay and Daisy is notorious and ultimately ends in tragedy, but it is a deeply moving experience for the audience. Luhrmann’s typically dazzling look The Great Gatsby is a memorable and raw portrayal of the highs and lows of love.
8 Beautiful in pink
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The iconic 1986 teen rom-com Beautiful in pink tells the story of a love triangle between a girl who must choose between her feelings for her childhood best friend and a rich but sensitive player. The ’80s darlings Molly Ringwald, Jon Cryer and Andrew McCarthy portray the trio in love in the quintessential ‘Brat Pack’ movie written by the beloved John Hughes and directed by Kind of beautiful‘s Howard German.
Recognizable and down-to-earth Andie (Ringwald) is in love with the preppy rich boy Blane, completely unaware that her best friend and fellow outsider Duckie has been pining for her for years. The original ending actually had underdog Duckie get the girl, but the test audience cheered that ending, and Hughes rewrote it so Andie and Blane could get together instead. Sorry, Duckie.
7 My best friend’s wedding
Undoubtedly one of the most popular unrequited love films of the 90s and 1997 rom-coms My best friend’s wedding follows a woman who realizes she is in love with her best friend after he announces his engagement. She then goes on a mission to win him over and tell him how she feels, despite his fast approaching marriage. Julia Roberts stars as Jules, whose best friend Michael (Dermot Mulroney) becomes engaged to the bubbly and sweet Kimmy (Cameron Diaz). Sabotage and hijinks naturally follow, culminating in a bittersweet finale. My best friend’s wedding is heavily regarded as one of the greatest romantic comedies of all time and is a beloved staple.
6 (500 days of Summer
Romantic drama from 2009 (500 days of Summer plays Joseph Gordon-Levitt and Zooey Deschanel and focuses on the hopeless romantic Tom Hansen as he reflects on his failed relationship with the girl he believes is his soul mate. He sets out to find out what went wrong and win her back by analyzing the various events of their 500-day courtship. Summer doesn’t believe in true love and Tom is a diehard romantic, so naturally tensions run high and they face problems. The refreshing rom-com (created at the height of the ‘manic pixie dream girl’ fandom) is unusual, charming and unique in its stories as it tells the audience how it will end at the very beginning with head Tom wondering why.
5 Brokeback Mountain
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Neowestern romantic drama Brokeback Mountain depicts the complex and moving emotional and sexual relationship between two American cowboys over the course of 20 years. Heath Ledger stars as Ennis Del Mar and Jake Gyllenhaal as Jack Twist, a pair of shepherds who fall in love and endure a heartbreakingly raw and tragic romance. Their love story is beautifully sassy and shows the efforts Ennis and Jack make to suppress their passion and overpowering feelings. Brokeback Mountain Heralded as a turning point for queer cinema’s progression into the mainstream, it features one of the most gripping and heartbreaking endings in the film yet.
4 Forgot Sarah Marshall
On the more comedic side of unrequited love, Jason Segel wrote and starred in 2008’s comedic farce Forgot Sarah Marshall, which follows devastated composer Peter as he escapes on a Hawaiian vacation after his TV star girlfriend Sarah breaks up with him. Kristen Bell stars as the titular Sarah, who leaves Peter for British rock star Aldous Snow (Russell Brand) and happens to go on vacation at the same resort where her ex is.
Peter must deal with his heartbreak and grief, while still longing for Sarah and their broken relationship. Mila Kunis stars as resort receptionist Rachel, who helps Peter overcome his anxiety-induced slump and shows him that love can blossom again. The film is a funny look not only at unrequited love, but also at how people eventually get over it.
3 To all the boys I’ve loved before
The Netflix teen romcom To all the boys I’ve loved before is based on the 2014 novel by Jenny Han and revolves around a teenage girl whose life is turned upside down when her secret love letters are revealed. Starring Lana Candor and Noah Centineo as Lara Jean and her crush Peter, the film follows Lara Jean as she deals with the fallout from her love letters emailed to all her crushes and their diverse reactions. To all the boys I’ve loved before is one of the much-needed mainstream romance films starring people of color, and is a sweet and heartwarming rom-com that was a runaway hit for Netflix, and its success led to two sequels.
2 The holiday
In the star-studded romantic comedy Nancy Meyers The holiday, two dejected women on opposite sides of the world decide to swap homes over the Christmas season in hopes of escaping their respective messy love lives. Kate Winslet and Cameron Diaz appear as London society columnist Iris and Los Angeles movie trailer producer Amanda, who try to do some much-needed self-reflection after their troubled relationships end. Iris is still madly in love with her ex, despite the fact that he emotionally manipulates her and has repeatedly cheated on her, so she heads to sunny California after being caught off guard by his engagement announcement. The feel-good film, which has become an inspiring Christmas staple in recent years, describes the growth both women experience when they discover that their self-esteem and satisfaction lies in themselves and not in a partner.
1 He’s just not that into you
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Based on the self-help book by Greg Behrendt and Liz Tuccillo, the 2009 epic rom-com features an all-star ensemble cast including Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Ben Affleck, and a plethora of more talented actors. The film focuses on nine people and their various romantic problems as they try to navigate the world of dating and romance. From unrequited affection to misinterpreting romantic interests, He’s just not that into you is an entertaining and enlightening film that sharply analyzes the treacherous realities of love and relationships.
The wide array of cast and characters makes the rom-com sparkle from start to finish, and the title alone screams “unrequited love.” He’s just not that into you is a real crowd pleaser who wants to entertain his audience – sometimes a movie loves you even when people don’t.