20 Best Movies About Unrequited Love

Summary Unrequited love movies showcase one-sided romantic feelings that aren't always reciprocated, adding depth to the drama and conflict.

Love triangles, star-crossed lovers, and unrequited crushes are popular sub-genres in romantic dramas that captivate audiences.

Some of the lesser-known unrequited love stories provide unique and artistic perspectives that can be found on various streaming platforms.

The subject of unrequited love remains consistently popular in both romantic comedies and romantic dramas. Unrequited love movies aren't just about romantic feelings that aren't reciprocated. Often, love is one-sided because it isn't openly acknowledged or labeled as such. This often makes for a very entertaining movie, because conflict is the very essence of drama and romance stories. Though these kinds of stories aren't fun for the characters, they are often some of the most touching for viewers to enjoy.

Whether it's a love triangle, a lover who can't let go of their ex, or a star-crossed love story, tragic or rocky love stories are one of the most widely viewed sub-genres. Many of the most popular unrequited love stories, but also some of the more artistic, lesser-known ones, can now be found across different streaming services. Many romantic comedies and other romantic movies miss the mark, but these are some of the best in this niche.

Related 10 Best Romantic Comedies From The Early 2000s That Will Make You Nostalgic Hollywood was obsessed with romantic comedies in the early 2000s, and this boom produced a number of classics that fans still watch today.

The Breaker Upperers (2018)

Stream on Netflix

This movie is about the exact opposite of matchmakers, which are more common in romantic comedies. Cynical after their past breakups, best friends Jen (Jackie van Beek) and Mel (Madeleine Sami) establish an agency designed to break couples up in unsuspecting ways. However, their hilariously over-the-top schemes are more of a reflection of their own personal problems and histories. They once dated the same guy, and one of them is still nursing feelings for him despite it being years earlier.

While not one of the more well-known unrequited love movies out there, critics loved the New Zealand romantic comedy, certifying it fresh on Rotten Tomatoes. It also became the top-selling movie in New Zealand for 2018. The two stars of the movie also co-wrote the movie and co-directed it, pulling triple duty for the comedy.

John Tucker Must Die (2006)

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Jesse Metcalfe is the titular John Tucker, a teenage boy who finds himself the target of a revenge plot when he dates three girls at the same time without telling him. Sophia Bush, Arielle Kebbel, and Ashanti team up with the new girl in school, Brittany Snow, to make him fall for her just so they can break his heart. While each of the girls want to hurt him, they also all clearly want him back, and each have moments of considering reconnecting with him.

Snow's character emulates the best traits from each of the girls he dated to pretend to be his perfect girl, and he does fall for her while she’s falling for his brother. John Tucker learns exactly what it’s like to fall and have his heart broken, but he's not the only character who learns a lesson at the end of this movie. The movie remains so popular among those who were teens in the 2000s that a sequel has been in development with the original cast.

There’s Something About Mary (1998)

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In the late 1990s, Cameron Diaz starred in two iconic movies about unrequited love. There’s Something About Mary is the raunchier of those two comedies. Diaz stars as Mary, an orthopedic surgeon who finds herself pursued by several different men. One of them is her high school prom date who couldn’t end up going with her but hires a private investigator to find her years later when he’s still in love with her. Another is the private investigator. Yet another is someone who pretends to be her friend but has really been stalking her.

Each of the men in the movie lies and tricks Mary - supposedly in the name of love - highlighting the dangers of obsession in a comedic way. The cast all have stellar comedic timing, making for what would be alarming scenes in a drama leave the audience hilariously entertained.

When We First Met (2018)

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Adam DeVine stars in this Netflix original movie as a man who firmly believes he met the perfect woman for him - but now she’s engaged to someone else. Though Noah (DeVine) and Avery (Alexandra Daddario) are friends, he wishes he had a second chance with her, and thanks to a photo booth that transports him back to the day they met, he does. Every decision he makes, however, to try to win her over changes the present day drastically.

When We First Met makes for an interesting take on a time loop movie since the main character is choosing to enact a time loop instead of being stuck in one. That's part of what makes it so entertaining. Of course, Noah has to learn that maybe his love for Avery is meant to remain unrequited because everything has worked out just the way it was supposed to.

Paper Towns (2015)

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When Margo (Cara Delevinge) suddenly vanishes, the boy next door (Nat Wolfe) is convinced she’s been leaving him clues to follow her to where she ran away. He’s had a crush on her forever, and despite her never showing romantic interest in him seemingly outside of a night of pranking with her, he convinces his friends to go on a road trip with him to track her down.

Based on the book by John Green, Paper Towns tells the story of what happens when someone’s love for another, whether it's reciprocated or not, allows them to believe the best of the other person. Quentin firmly believes that Margo is the best and someone who wouldn't just abandon her life. He feels a responsibility to find her because of his feelings for her, but he discovers just how his perception has been skewed by his own feelings.

He’s Just Not That Into You (2009)

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He’s Just Not That Into You explores love in several different forms, like married couples facing difficulties or conflicting interests for couples where one partner wants to marry, and the other doesn't. The movie allows all manner of relationships to unfold, including unrequited love.

Ginnifer Goodwin’s character gets a lesson in how to take rejection from those she’s interested in while someone who least expects to fall for her does. Scarlet Johansson’s character only seems to fall for men she can’t have, and those who fall for her are ones she only sees as friends. Many of the relationships and stories in the movie interweave, inspired by the self-help book of the same name. The movie examines the many forms of rejection, love, and the tropes the audience has seen in romantic comedies with a fresh lens.

Related He's Just Not That Into You: 10 Best Quotes, Ranked The rom-com He's Just Not That Into You was released over 10 years ago. Here are 10 of the best quotes, ranked.

Sense and Sensibility (1995)

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Emma Thompson’s 1995 adaptation of Jane Austen’s Sense and Sensibility is one of the best-known Austen projects on the big screen. Though Pride and Prejudice has had more adaptations over the years and Amy Heckerling's Clueless is one of the most memorable modern Austen adaptations (of Emma), Thompson’s script managed to make Sense and Sensibility more accessible for a modern audience while maintaining the spirit and time period of the story.

In the story, nearly every main character is in love with someone who happens to be in love with someone else. The romantic entanglements and the confines of society when it comes to women of the time are what drive the story. Ultimately, the Dashwood sisters (Thompson and Kate Winslet) do get their happy endings, but not necessarily with whom the viewers initially expect.

The Perks Of Being A Wallflower (2012)

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The Perks of Being A Wallflower certainly features a memorable story of unrequited love. Though unrequited love plays a role in The Perks of Being A Wallflower, the larger story is of acceptance and growth during adolescence.

Charlie (Logan Lerman) has been suffering under the weight of his depression and struggles to adapt during his freshman year of high school following the death of his best friend. He’s taken into the friend group of Sam (Emma Watson) and Patrick (Ezra Miller). When Charlie’s feelings for Sam become clear to the group, he’s asked to “stay away” for a while because he’s hurt the girlfriend he has by choosing Sam over her. Despite that, Sam and Patrick still clearly care for him and value his friendship, proving that the bonds they have can survive unrequited romantic love.

To All the Boys I've Loved Before (2018)

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To All the Boys I've Loved Before employs many familiar coming-of-age and romantic comedy tropes, but with a refreshing twist that makes the movie as good, if not better, than the young adult novel on which it is based. Lara Jean is a high school student who wrote (but didn't send) letters to boys she's had crushes on. She sees these crushes as unrequited love, and her feelings are so big that she has to get them out and on paper.

One of these boys receives Lara Jean's old letter when her younger sister mails them. Peter wants to use Lara Jean to make his ex jealous, but she still has feelings for him. The plot itself isn't entirely original, but the film's tone is. The colorful cinematography and production design make this Netflix trilogy (and spin-off series featuring Lara Jean's younger sister) a delightful treat.

Malèna (2000)

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Many of the movies centering on unrequited love fall into the romantic comedy category. Malèna does not. The drama, set in a small town in Italy, sees several men in town develop feelings, and in some cases, obsessions with the woman Malèna.

She lives alone because her husband is a soldier, and she becomes a target of some of the townspeople when she has a relationship with another soldier. A young boy in town decides to try to become her protector, loving her from afar, but unable to help her when the women in town take out their anger on her. It’s Renato who eventually tells her returning husband where to find her as she has left town, and it’s Renato who remembers her story decades later because she’s the only woman he’ll never forget.

Ghost World (2001)

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Inspired by the comic book of the same name, Ghost World is a coming-of-age story that follows two teenage girls in the summer after they graduate from high school. Rebecca (Scarlett Johansson) and Enid (Thora Birch) find themselves growing apart as they both become interested in different things. As they grow apart, Enid becomes focused on an older man named Seymour (Steve Buscemi) after pranking him.

Though she works to find him a new romantic partner, she also develops feelings for him and grows jealous of the women she sets him up with. When Seymour discovers Enid’s initial prank, their friendship sours, and Enid has to find a way to move on with her life. Since its release, Ghost World has become a cult classic and was added to the Criterion Collection in 2017.

Pretty In Pink (1986)

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A John Hughes classic, Pretty in Pink features Molly Ringwald as Andie, a teenage girl who lives with her single dad and doesn’t fit in with the rich crowd at school. Her best friend Duckie (Jon Cryer) is usually her rock, but when a wealthy and popular boy (Andrew McCarthy) starts to take an interest in her, their friendship suffers. That’s because Duckie has feelings for Andie and grows jealous of her spending time with someone else.

Much of Andie’s story focuses on the conflict of a working-class girl trying to date a wealthy boy, but Duckie’s story of his seeming unrequited love plays out alongside hers. Duckie, however, eventually realizes he would rather Andie be happy with someone else than miserable while he pines for her. It's a coming-of-age story of acceptance and moving on.

Related Every John Hughes & Molly Ringwald Movie, Ranked Worst To Best Although Molly Ringwald has a bit of a tainted view on the films now, John Hughes' 1980s movies with her are some of the most influential teen movies.

Love, Actually (2003)

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Much like He’s Just Not That Into You, Love, Actually features a huge ensemble cast and explores love in its many forms. While there are breakups, new relationships, first crushes, and failed affairs, there is also unrequited love in the movie, exemplified by one of Love, Actually’s most remembered moments.

Before starring in The Walking Dead, Andrew Lincoln played a man in love with his best friend’s new wife, played by Keira Knightley. She’s always wondered why he’s treated her so coldly, and it’s only after seeing how he’s filmed her wedding day that she realizes he has feelings for her. While things are initially awkward, and he professes his love for her with poster board and Christmas carols in front of her house, they do work their way toward a friendship in the end.

American Beauty (1999)

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When American Beauty first hit theaters in 1999, it received a lot of critical praise and prestigious awards, though audiences don’t always look back on it as favorably today. That’s largely because the unrequited love of the movie is more like unrequited and inappropriate infatuation with a 42-year-old man (Kevin Spacey) developing a fixation on his daughter’s 16-year-old friend (Mena Suvari). That fixation slowly begins to ruin all of the relationships he has.

Ultimately, he doesn’t pursue his feelings for her because he realizes that he doesn’t truly have a romantic interest in her. The movie aimed to look for beauty in the mundane, but it also put a magnifying glass on just how the idea of the American dream could be twisted, and it did that through the fantasy of this inappropriate relationship.

Welcome to the Dollhouse (1995)

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Dawn (Heather Matarazzo) is a junior high student who gets picked on at home and picked on at school. There doesn't seem to be anywhere she can turn to be accepted or feel loved. When she develops a crush on her older brother’s new bandmate, things just get worse for her.

Her school bully also turns out to have feelings for her, which she can’t return, but the love triangle isn’t what motivates the story. Welcome to the Dollhouse is a snapshot of adolescence when everyone feels like they don’t belong; the unrequited love stories that play out are simply part of growing up as they are, in reality, crushes that will fade over time. When Dawn is just on the cusp of growing up, however, her feelings seem larger than life, and she doesn't know that.

The Great Gatsby (2013)

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The Great Gatsby is a novel read by high-schoolers all over the world and analyzed again and again for its use of symbolism on the page. It has also been adapted for the screen more than once. Baz Luhrman’s adaptation, however, is the kind of visual spectacle F. Scott Fitzgerald, someone who lived when the 1920s really did roar, would likely have loved.

Leonardo DiCaprio stars as the titular Gatsby who embraces the life of the roaring ‘20s with opulent parties for his closest friends and high society members. He does so, however, because he’s in love with Daisy Buchanan (Carey Mulligan), and does everything he can to stay in her good graces. Unfortunately for Gatsby, his love for her isn’t exactly reciprocated and his efforts end in tragedy, not just for him, but for multiple characters.

Her (2013)

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Joaquin Phoenix stars in Her, which is a pretty unusual take on unrequited love for a movie. In Her, Phoenix’s character gets very attached to the AI providing the voice of his digital assistant. Like an iPhone’s Siri, she has answers to any question he asks and is there to offer him the support he needs just when he needs it. As a result, he begins to fall in love with her, only to find that she offers the same “love” and support to all of the digital system's users, crushing him.

This version of unrequited love speaks to the loneliness one person can feel and how technology can augment those feelings. Even as the world becomes more connected as a whole, people can still feel incredibly disconnected thanks to most of their connections happening behind a digital screen.

My Best Friend’s Wedding (1997)

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My Best Friend’s Wedding is probably one of the best-known movies about unrequited love to ever hit theaters. Julia Roberts stars as a woman convinced that she and her best friend (Dermot Mulroney) of two decades will end up together one day, only to be blindsided when he invites her to his wedding to someone else (Cameron Diaz).

She spends much of the time before the wedding trying to break them up, convinced that because she loved him first, she should be the one walking down the aisle. It takes a huge fight between the friends and her having to find the runaway bride for her to realize the error of her ways and be there for the happy couple. Though she doesn’t get a typical happily ever after, Roberts still shines in the movie.

The Holiday (2006)

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The Holiday is one of the most underrated rom-coms and the third hit to feature unrequited love for Cameron Diaz. Though most audiences will remember the love stories that blossom between Diaz and Jude Law and Kate Winslet and Jack Black, one of the most important moments in the movie is Winslet’s Iris realizing that she cannot put all of her energy into unrequited love.

What kicks off her decision to switch places with Diaz’s Amanda for the holidays is that she begins to understand that the man she loves is only using her for help with his work. Her holiday isn’t just about finding love, but about separating herself from him and learning to move on from someone who isn’t good for her. It’s a cathartic moment for the audience when she finally stands up to him.

Les Misérables (2012)

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The 2012 musical adaptation of Les Misérables is critically divisive, but it remains popular among moviegoers, and now, streamers. There is a huge cast of characters whose lives play out against the backdrop of the French Revolution. The main plot follows Jean Valjean's release from prison and his quest to begin a new life. Jean Valjean's daughter Cosette is the subject of admiration for Marius, a rebel and the son of a nobleman. He, in turn, is the subject of strong affection from Eponine, a street urchin.

So strong are her feelings that she sings a lamenting ballad of her unrequited love, one of the best-known among musical theater fans, "On My Own." It's Eponine, and her ultimate sacrifice during the battles of the revolution, that provides the story with its unrequited love, and the character is showcased beautifully by Samantha Barks. Eponine is one of the ultimate depictions of unrequited love in movies.