15 Best One-Sided Love Movies Of All Time

POSTED BY Natasah Carim, UPDATED ON March 14th, 2024
15 Best One-Sided Love Movies of All Time

Why do we gravitate towards love stories and romantic flicks? Maybe it’s because they soothe our broken hearts or give us a brief escape to a world where the hero always wins. Sadly, love is messy; sometimes, audiences want something more authentic, like a one-sided love story. Here are the top films ever made about unrequited, one-sided love.


15. My Best Friend’s Wedding (1997)

My Best Friend’s Wedding (1997)

My Best Friend’s Wedding is arguably one of the best romcoms ever that explores the cosmic interplay between love and friendship. Julianne, played by Julia Roberts, realizes her one-sided love for her best friend, Michael O’Neal (Dermot Mulroney), shortly after he announces his engagement.

Realizing she doesn’t want to lose him, she sets off to sabotage the upcoming wedding and end his relationship with Kimmy (Cameron Diaz). Ultimately, the series of hijinks led to an unforgettable yet bittersweet ending.


14. Her (2013)

Her (2013)

Given the rapid pace of technology advancements, Spike Jonze’s Her is a game-changer. It introduces the concept of developing intimate relationships with a sentient operating system – an idea that might seem far-fetched but isn’t entirely out of the question.

Lonely and introverted, Theodore (Joaquin Phoenix) grows emotionally attached to his AI-operated virtual assistant, Samantha (Scarlett Johansson). The movie raises provoking questions about how machines can become attuned to human emotions and transcend physicality when it comes to love.


13. The Holiday (2006)

The Holiday (2006)

In Nancy Meyer’s star-studded romcom The Holiday, two dejected women decide to swap houses during the festive season in hopes of some much-needed self-reflection after ending their messy relationships. Iris, a London Society columnist played by Kate Winslet, is still in love with her manipulative ex after being caught off guard by his engagement.

She sets out for sunny California, where movie trailer producer Amanda, played by Cameron Diaz, is based, who has recently experienced a similar situation. This feel-good movie has become a holiday staple, chronicling self-growth, discovery and fulfillment.


12. Forgetting Sarah Marshall (2008)

Forgetting Sarah Marshall (2008)

Written by and starring Jason Segel, Forgetting Sarah Marshall follows a depressed composer, Peter Bretter, who escapes to Hawaii after his TV star girlfriend, Sarah (Kristen Bell), breaks up with him. In a twist of events, Sarah and her new beau, British rock star Aldous Snow (Russell Brand), are vacationing at the same resort as him.

Although he misses Sarah, Peter must accept their broken relationship. Mila Kunis stars as receptionist Rachel, who finally helps Peter see a new perspective on getting over his anguish-ridden, unrequited love.


11. Pretty in Pink (1986)

Pretty in Pink (1986)

Pretty in Pink is often hailed as a cult classic as it tells the story of a teenage love triangle. Starring 80s sweethearts Molly Ringwald as Andie, Andrew McCarthy as Blane, and Jon Cryer as Duckie, the movie revolves around the complexities of young love, peer pressure, and social class distinctions.

Andie becomes romantically involved with preppy rich boy Blane, sparking tension and disapproval from their social circles. What Andie doesn’t realize is that her best friend, Duckie, has been pining after her for years.


10. All About Steve (2009)

All About Steve (2009)

As the title suggests, this movie is All About Steve. Starring Bradley Cooper (Steve) and Sandra Bullock as Mary, the film delves into the consequences of obsessively pursuing someone who doesn’t feel the same way. To prove her love for Steve, Mary embarks on a cross-country journey following Steve despite rejection– unbeknown to her, this adventure turns into a valuable lesson on her perception of love.

Through lightheartedness and humor, All About Steve also touches upon Mary’s possible neurodiversity in the context of romance.


9. The Great Gatsby (2013)

The Great Gatsby (2013)

Set in 1929, The Great Gatsby is an adaptation of F. Scott Fitzgerald’s classic novel. It tells the tale of Wall Street millionaire Jay Gatsby (Leonardo DiCaprio) and his unrequited love for Daisy Buchanan (Carey Mulligan) through the eyes of Nick Carraway (Tobey Maguire), an outsider who narrates his experience as a witness to the unfolding tragedy that awaits. Jay and Daisy’s love story begins long before World War I.

While Jay is away at war, Daisy has no other option but to move on and establish her life with another. Eventually, Jay returns and spends years building his entire life around the possibility of winning her back, even if it means welcoming death because of her. 


8. Forrest Gump (1994)

Forrest Gump (1994)

Another film adaptation, Forrest Gump, follows a low-IQ man through his ups and downs from childhood to adulthood, experiences in the Vietnam War, and accidental success at ping-pong. Even though Forrest couldn’t walk, the encouraging words of his childhood friend and lady love Jenny Curran (Robin Wright), “Run, Forrest, Run!” help him get on his feet.

Forrest’s love for Jenny remains constant no matter what life throws his way; however, her complex life choices leave her sinking into a pit of despair, complicating her feelings for Forrest as she bounces between being his friend and lover. Forrest’s story symbolizes innocence, kindness, and unwavering devotion to loved ones.


7. One Day (2011)

One Day (2011)

When strangers Emma Morley (Anne Hathaway) and Dexter Mayhew (Jim Sturgess) become friends over a kiss, they make a pact to meet on the same day every year to catch up. For two decades, the movie follows their lives as their paths cross repeatedly on the same day, providing a glimpse into their evolving feelings for each other. 

However, they are torn between their feelings and denial of them over a series of missed opportunities, friendship, love, and the unstoppable passage of time.


6. 500 Days of Summer (2009)

500 Days of Summer (2009)

Hardcore rom-com fans swear by this Mar Webb masterpiece. It’s not your typical love story where protagonists break up and eventually find their way back. Instead, it’s about overcoming the fear of moving on and finding true love despite the emotional trauma of heartbreak.

The events in 500 Days of Summer follow the life of greeting card writer Tom (Joseph Gordon-Levitt) and his coworker Summer (Zooey Deschanel), who become romantically involved. However, it’s evident from the get-go that Summer does not share Tom’s views on long-term commitments. The non-linear narrative and endearing performances make this movie a must-watch!  


5. There’s Something About Mary (1998)

There's Something About Mary (1998)

The Farrelly brothers followed up the success of Dumb and Dumber with a fusion of confusion and love. There’s Something About Mary won several awards and nominations with its star-studded cast featuring Ben Stiller as Ted and Cameron Diaz as Mary.

The movie begins with a failed prom date but ends with Ted trying to unravel a web of deceit. Recruited by Ted to help him pursue Mary, Tucker (Lee Evans) and Pat (Matt Dillon) fall in love with her instead. The film piques your curiosity as you’re left eager to know what happens next.


4. Ghost World (2001)

Ghost World (2001)

Packed with satirical humor and a sharp portrayal of disaffected early 2000s youth, Ghost World underscores the world of teenage outcasts Enid (Thora Birch) and Rebecca (Scarlett Johansson).

When they find themselves at a crossroads after graduation, Enid makes it her priority to help lonely middle-aged record collector Seymour (Steve Buscemi) find love. However, as fate may have it, she materializes a crush on Seymour herself. Although Ghost World isn’t your typical romance, it explores the challenges of growing up and the quest for meaningful relationships.


3. Chungking Express (1994)

Chungking Express (1994)

Chungking Express is a quintessential Wong Kar-wai masterpiece. In a parallel storyline, the movie explores the love lives of two police officers, Cop 663 (Tony Leung Chiu-wai) and Cop 223 (Takeshi Kaneshiro). Cop 223 is coping with a recent breakup when he meets a mysterious, disguised woman involved in illegal drug smuggling, leading to a series of unexpected events.

Simultaneously, an upbeat waitress named Faye becomes infatuated with Cop 663, who visits her restaurant regularly. Both stories’ chance encounters and brief intersections are symbolic marvels as they share the search for meaning in the bustling, fast-paced city life.


2. The Perks of Being a Wallflower (2012)

The Perks of Being a Wallflower (2012)

Set in the 1990s, the movie follows the life of socially awkward teenager Charlie, played by Logan Lerman, as he embarks on a journey of self-growth and everlasting friendships.

As an introvert, Charlie initially finds it difficult to make friends due to struggles with a traumatic past. That is until he befriends two seniors, Sam (Emma Watson) and her stepbrother Patric (Ezra Miller), who take him under their wing and introduce him to a world of new experiences. Inevitably, Charlie falls in Love with Sam, but she is in a relationship with someone else. The Perks of Being a Wallflower is a heartfelt dive into the world of mental health and raw adolescent emotions.


1. The Age of Innocence (1993)

The Age of Innocence (1993)

Martin Scorsese redefined his name in the movie world with this romantic drama. Starring a trio of legends Michelle Pfeiffer (Countess Ellena Olenska), Winona Ryder (May Welland), and Daniel Day-Lewis (Newland Archer), The Age of Innocence highlights the depths of trust, promise and desire.

The period drama is set in 1870’s New York City and begins when the Countess returns to New York After a failed marriage. Captivated by her unconventional spirit, Newland finds himself torn between marrying his fiancé May or pursuing his true desires. The film is known for its meticulous attention to detail, award-winning costume design, and critically acclaimed portrayal of social norms at the time.

What are your favorite one-sided love movies of all time? Let us know in the comments!

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