32 Heartbreaking Movies About Unrequited Love

32 Heartbreaking Movies About Unrequited Love

As a film enthusiast who’s spent countless hours immersed in the world of celluloid love stories, I must say these movies truly resonate with my heartstrings. Each one tells a unique tale of love, longing, and heartache, mirroring the complexities of human emotions.


This age-old story revolves around an individual’s affection for someone else, yet left untouched due to various reasons. Sometimes it’s societal expectations, sometimes the timing simply isn’t ideal, and at other times, it’s plain indifference. Here are some heart-wrenching instances of unrequited love portrayed in movies.

32 Heartbreaking Movies About Unrequited Love

Past Lives

2023’s “Past Lives” was a splendid film. The heartwarming and poignant tale of “The Celine Song,” written and directed by an unnamed artist, follows the story of two young friends in South Korea who always seem to miss the perfect moment for their friendship to blossom into romance. In the end, both the audience and the characters are left pondering what might have been.

32 Heartbreaking Movies About Unrequited Love

Love Actually

The scene between Andrew Lincoln and Kiera Knightly in Love Actually offers perhaps the most poignant portrayal of unrequited love on screen. Remember the moment when Mark (Lincoln) confesses his love for Juliet (Knightly) by placing posters with heartfelt messages at her door? Although she’s moved, they both come to understand that their relationship will remain platonic forever.

32 Heartbreaking Movies About Unrequited Love

Casablanca

In the iconic movie Casablanca, Rick (Humphrey Bogart) and Ilsa (Ingrid Bergman) are perpetually unable to find the perfect moment for their love. This timeless tale of unrequited love is one of the most poignant portrayed on screen, as these two kindred spirits reminisce about a past filled with enchantment that they can never reclaim. Ultimately, they make the difficult choices, act honorably, and accept that their relationship will remain unfulfilled. They will forever cherish Paris.

32 Heartbreaking Movies About Unrequited Love

(500) Days Of Summer

500 Days of Summer can be summed up as the timeless portrayal of an unfulfilled love tale. In this movie, Tom (played by Joseph Gordon-Levitt) and Summer (Zooey Deschanel) initiate a noncommittal relationship that Summer is transparent about in the beginning. However, as Tom develops feelings for her, Summer maintains a casual approach until their relationship reaches a climax, leaving Tom heartbroken.

32 Heartbreaking Movies About Unrequited Love

Rushmore

Among the listed examples, Wes Anderson’s 1998 film Rushmore is one of the more awkward ones. The protagonist, high school student Max Fischer (Jason Schwartzman), develops feelings for a teacher (Olivia Williams), while his classmate Margaret (Sara Tanaka) reciprocates those feelings towards Max. However, neither of them finds favor with their crushes, leading to an increasingly complex predicament.

32 Heartbreaking Movies About Unrequited Love

Forrest Gump

Forest Gump, portrayed by Tom Hanks, isn’t known for his intelligence, but he is incredibly loyal. From his early years, he harbors a deep affection for Jenny (Robin Wright), his childhood friend. Despite the extraordinary experiences that shape his life, his love for Jenny never wavers. However, Jenny, who shows a unique form of loyalty towards Forest, leads a life quite unlike his own and repeatedly pushes him away throughout her journey, until the very end of her tumultuous existence.

32 Heartbreaking Movies About Unrequited Love

Brokeback Mountain

One powerful illustration of societal constraints preventing two lovers from experiencing the affection they yearn for together is the film “Brokeback Mountain.” Characters Ennis (played by Heath Ledger) and Jack (Jake Gyllenhaal) share a deep passion, but their community’s intolerance prevents them from openly expressing it, resulting in a poignantly tragic predicament.

32 Heartbreaking Movies About Unrequited Love

The Royal Tenenbaums

In simpler terms, one of the most unusual and disquieting instances on this list is the relationship between Richie Tenenbaum (played by Luke Wilson) and his sister Margot (portrayed by Gwyneth Paltrow). Their affection creates situations that are undeniably awkward. The love they share is clearly taboo, and it’s not always easy to support their romantic endeavors.

32 Heartbreaking Movies About Unrequited Love

The Great Gatsby

In simple terms, F. Scott Fitzgerald’s renowned novel “The Great Gatsby” serves as a powerful illustration of the devastating impact of unfulfilled love. In the movie adaptation directed by Baz Luhrmann, Leonardo DiCaprio portrays the character of Gatsby, who deeply laments his decision to ask Daisy (played by Carey Mulligan) to postpone their relationship. Unfortunately, Daisy marries George (Jason Clarke), leading to a series of unfortunate events.

32 Heartbreaking Movies About Unrequited Love

Lost in Translation

In a Tokyo hotel, we encounter Bob (played by Bill Murray) and Charlotte (portrayed by Scarlett Johansson), both content in their respective marriages. An unexpected meeting sparks a connection as they explore the city together. However, the atmosphere remains tense due to their uncertainty about each other. No romantic advances are made until the climax of the film, where they exchange a kiss, leaving the outcome uncertain – could this be the start of something new?

32 Heartbreaking Movies About Unrequited Love

Pretty In Pink

A timeless illustration of a love going unrequited is that of Duckie (Jon Cryer), who in the film “Pretty In Pink“, adores Andie (Molly Ringwald) and would do anything for her. Despite being deeply appreciative of Duckie’s devotion and companionship, Andie harbors feelings for Blaine (Andrew Shue). Ultimately, she picks Blaine at the end, causing disappointment among some viewers of the movie.

32 Heartbreaking Movies About Unrequited Love

Doctor Zhivago

In the timeless film “Doctor Zhivago,” portrayed by Omar Sharif as Yuri Zhivago and Julie Christie as Lara, one of cinema’s most enduring love stories unfolds. Regrettably, due to the tumultuous circumstances of war and other romantic entanglements, they are unable to experience the blissful conclusion often associated with “happily ever after.”

32 Heartbreaking Movies About Unrequited Love

There’s Something About Mary

In the movie “There’s Something About Mary,” it’s clear that everyone, including football star Brett Favre, has a crush on Mary (Cameron Diaz). However, due to her romantic entanglements, many men find themselves heartbroken. The film concludes with one man, Ted (Ben Stiller), winning Mary’s affection, but the question remains: what about the countless other suitors who were left disappointed? After all, Brett Favre did nothing wrong!

32 Heartbreaking Movies About Unrequited Love

Great Expectations (1998)

1998’s adaptation of Great Expectations, set in contemporary New York City, retells the timeless Charles Dickens narrative. Ethan Hawke portrays Finn, who develops feelings for Estella, played by Gwyneth Paltrow. However, Estella is elusive and, to put it mildly, unkind towards him. She manipulates his affections and employs him to provoke her fiancé’s jealousy. Despite the passage of years, Finn never lets go of his feelings for her, and eventually, she reciprocates his love.

32 Heartbreaking Movies About Unrequited Love

La La Land

In La La Land, Seb (played by Ryan Gosling) and Mia (portrayed by Emma Stone) show a deep passion for each other, but their romantic connection never quite aligns perfectly. Despite numerous opportunities throughout the film, it seems that timing is always off for them, ultimately leading to their tragic separation – a fate seemingly predestined for these two characters.

32 Heartbreaking Movies About Unrequited Love

Les Misérables

In the tale Les Misérables, there’s a well-known instance of unrequited affection in Western literature. Characterized by Samantha Barks in the 2012 movie adaptation of the musical, Eponine harbors feelings for Marius that he doesn’t reciprocate. This emotional turmoil culminates in an incredibly moving rendition of the song “On My Own” on screen.

32 Heartbreaking Movies About Unrequited Love

Roxanne

Steve Martin’s lesser-known comedy film, titled Roxanne, draws inspiration from the well-known play, Cyrano de Bergerac. Similar to Cyrano, Steve Martin’s character, C.D., boasts numerous attractive qualities, but his unusually large nose hinders him from openly declaring his love for Roxanne (played by Daryl Hannah).

32 Heartbreaking Movies About Unrequited Love

My Best Friend’s Wedding

Title summarizes the story: “My Best Friend’s Wedding” is another moving illustration of unrequited feelings between two close friends. They might harbor deeper emotions, but fail to act, only to realize their chance has passed when one or both move on. This realization brings difficulty for everyone involved.

32 Heartbreaking Movies About Unrequited Love

Chasing Amy

In the film “Chasing Amy,” there are certain issues that we won’t delve into now. Regardless of these complications, the core narrative revolves around a man, portrayed by Ben Affleck, who is in love with a woman, Joey Lauren Adams’ character. Although she doesn’t return his feelings, it’s not her responsibility to do so, yet the emotional turmoil experienced by Affleck’s character, Holden, remains deeply moving at the film’s conclusion.

32 Heartbreaking Movies About Unrequited Love

Once

In “Once,” I found myself drawn into the poignant tale of two musicians, their artistic bond mirroring an unspoken romantic connection that never quite materialized due to circumstances beyond their control. Despite both of them seemingly yearning for it, life and destiny kept them separated – a bittersweet narrative that’s both melancholic and heartwarming at the same time.

32 Heartbreaking Movies About Unrequited Love

To All the Boys I’ve Loved Before

Lara Jean Covey, portrayed by Lana Condor, shares similarities with many high school students in certain aspects. Just like us, she experienced unrequited crushes during her teenage years, but what makes her unique is her unusual way of dealing with them – composing letters that she keeps secret instead of sending them. However, when these letters are accidentally discovered, a complex web of love triangles and numerous heartaches ensue.

32 Heartbreaking Movies About Unrequited Love

The Remains of the Day

In grand English manors, James Stevens and Sally Kenton (portrayed by Anthony Hopkins and Emma Thompson) work as servants who share a relationship that appears deeper than just professional acquaintance. However, it’s complex and seems to hold more emotion than they are willing or able to express. Sally harbors strong feelings for James, but he remains closed off, unwilling to reciprocate. Regret fills them both in the end, as their unrequited love remains just that – unfulfilled.

32 Heartbreaking Movies About Unrequited Love

Forgetting Sarah Marshall

In simpler terms, character Peter Bretter (played by Jason Segel) continues to pine for his former partner, Sarah (Kristen Bell), even after she’s moved on with a new partner, portrayed by Russell Brand. Their shared vacation at the same Hawaiian resort only intensifies Peter’s longing and hinders him from recognizing that Rachel (Mila Kunis) might be a more suitable romantic match. However, in due time, he comes to understand the right choice.

32 Heartbreaking Movies About Unrequited Love

Edward Scissorhands

Poor Edward (Johnny Depp) in the movie Edward Scissorhands. He never truly gets an opportunity to find genuine love, despite his evident feelings for Kim (Winona Ryder). She also confesses her affection for him eventually, but they both understand that their relationship is impossible and part ways forever.

32 Heartbreaking Movies About Unrequited Love

The Last Of The Mohicans

In many timeless tales of unrequited love, “The Last of the Mohicans” portrays Hawkeye (Daniel Day-Lewis) and Cora (Madeleine Stowe), who are deeply in love but can’t experience lasting happiness due to the constraints of their historical era and the tumultuous backdrop of war. Despite their efforts, external factors prevent them from living a blissful life together.

32 Heartbreaking Movies About Unrequited Love

West Side Story

One timeless illustration of doomed romance is none other than Shakespeare’s “Romeo and Juliet.” Countless adaptations of Shakespearean tales have graced our screens, and among the best is the iconic “West Side Story.” Characters ensnared in the tug-of-war between their love and their allegiance to their gangs find it unbearable to stay apart, crafting a heartbreaking narrative that stands among the most poignant tales ever penned.

32 Heartbreaking Movies About Unrequited Love

An Affair to Remember

In the film “An Affair to Remember,” I found myself yearning for a love story that could’ve been extraordinary between Nickie (Cary Grant) and Terry (Deborah Kerr). It appeared as if destiny was bringing us together, two souls trapped in unhappy relationships, ready to break free and embrace our passion. But just when it seemed like we were about to escape our misery, an unforeseen twist of fate cruelly kept us apart. Or so I thought. The question remains: Will the stars align once more, allowing us a chance at happiness?

32 Heartbreaking Movies About Unrequited Love

He’s Just Not That Into You

It seems clear that the title itself provides sufficient understanding about the film’s content, correct? “He’s Just Not That Into You” is a movie featuring a stellar cast, where the characters find themselves entangled in complicated romantic situations with unreturned affections abound.

32 Heartbreaking Movies About Unrequited Love

One Day

For two decades, Dexter (Jim Sturgess) and Emma (Anne Hathaway) have been subtly expressing romantic interest in each other. They’ve always maintained a strong friendship, yet there are instances where one or both of them secretly yearn for something more. However, these desires never seem to align at the same moment.

32 Heartbreaking Movies About Unrequited Love

Her

Indeed, this tale is quite unusual among the others. To elaborate, it revolves around an unrequited love between a man, portrayed by Joaquin Phoenix, and a computer program that speaks through Scarlett Johansson’s voice. Can you understand now why their relationship doesn’t blossom?

32 Heartbreaking Movies About Unrequited Love

Broadcast News

80’s gem, Broadcast News, might not get the recognition it deserves nowadays, having been nominated for numerous Oscars. Yet, its timeless tale remains a favorite of mine. The intricate love triangle among the main characters is far from simple and tidy – none find their happily-ever-after together. Instead, they’re all left grappling with the complexities of unrequited feelings and missed connections. It’s a poignant reminder that sometimes love isn’t about finding the perfect match, but navigating the messiness of human emotions.

32 Heartbreaking Movies About Unrequited Love

Paper Towns

Unrequited high school love is something most people are familiar with and Paper Towns tells a fairly straight forward version of the classic tale of the socially awkward kid in love with the popular kid. Even though it’s not the most original of stories, it’s told in a great way and is a surprisingly sweet movie. 

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2024-08-31 17:38