15 Saddest Romantic Movies of All Time

POSTED BY , UPDATED ON March 14th, 2019


7. Blue Valentine (2010)

Blue Valentine 2010 Movie

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Starring Ryan Gosling and Michelle Williams, Blue Valentine showcases numerous predicaments that seep in a marriage that began with deep love and mutual respect. In the case of their respective characters, Dean and Cindy try everything in their hands to keep their marriage intact but end up with little to no success.

From alcohol struggles to emotional outbursts, Dean finally realizes that his daughter Frankie should not grow up in a house in which her parents constantly engage in verbal fights. As one of the saddest closing moments in sad romantic movies, Dean walks away from his home as his daughter cries for him while being held in Cindy’s arms. 


6. Boys Don’t Cry (1999)

Boys Dont Cry 1999

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Guaranteed to make you weep and rethink about hate crimes in America, Boys Don’t Cry is not only based on a true story but also faithful to the source material. Hilary Swank portrays Brandon Teena, a transsexual male who was brutally raped and murdered in cold blood.

His relationship with Lana Tisdel is cut short when their male friends violently murder him after finding out the truth about him being a transgender.

With Lana helplessly looking on while he is shot to death, the scene was incredibly uncomfortable to witness. Apart from the movie receiving praise from critics, fans and the LGBTQ community, Swank won the Academy Award for Best Actress.


5. La La Land (2016)

La La Land 2016

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Hollywood’s heartthrob Ryan Gosling pops up in the list yet again! La La Land earned thirteen Academy Award nominations and won six and to top it all off, it proved that musical movies are not a dying art.

Centralizing on two people with big dreams trying to make a name for themselves in Hollywood, Sebastian Wilder is a jazz pianist and Mia Dolan is an aspiring actress. Both spark a fire in one another to refuel the passion for their art but due to several rocky episodes in their relationship, they soon call it quits.

Five years later, Sebastian and Mia (now married) have achieved their professional goals and meet each other at a jazz bar and realize that while they are at the top of their game, it occurred at the cost of losing one another.


4. Shakespeare in Love (1998)

Shakespeare in Love 1998

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It could not be denied that the fictional love story of English playwright William Shakespeare as comprehended in Shakespeare in Love is one of the most enticing love tales in cinematic history.

Though Shakespeare and his love interest Viola De Lesseps do not end up together, the movie enjoyed a happy ending at the Academy Awards ceremony by winning in seven categories including Best Picture from its thirteen nominations.


3. Letter from An Unknown Woman (1948)

Letter from An Unknown Woman 1948

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When teenager Lisa Brendle falls in love with concert pianist Stefan Brand, her obsession leads to stalking and eventually going out on a date with him. The romantic night ends with Lisa being pregnant and Stefan walking away from her life.

With the passage of ten years and not being in contact with one another, Lisa is married to another man and Stefan experiencing a downfall in his music career. Once they run into one another, he fails to recognize her and the two part ways once again.

Now gravely ill and battling for her life in a hospital, Lisa passionately writes down a letter for Stefan to explain who she was and how her love for him resulted in their son. Unfortunately, by the time Stefan realized who she really was, Lisa had breather her last.


2. Brokeback Mountain (2005)

Brokeback Mountain 2005

Initially labelled as a “gay cowboy movie”, Brokeback Mountain was definitely much more than that. When Jack Twist and Ennis Del Mar are hired to look after some sheep in Wyoming, they indulge in physical affection after a few drinks.

Despite agreeing to forget about the incident and categorizing it as just a one-time incident, things only get complicated when they intentionally extend their friendship to physical and emotional passion.

After parting ways and living a married life, the two rekindle their relationship once they after a few years. However, due to the social stigma of homosexuality in the society, the two never live a life together. Brokeback Mountain was the talk of the town at the night of the Academy Awards ceremony as leading actors Heath Ledger and Jake Gyllenhaal received nominations for Best Actor and Best Supporting Actor, respectively, while Ang Lee won one for Best Director.


1. Titanic (1997)

Titanic 1997

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Was there ever any ounce of doubt about the top spot? The final moments of Rose holding on to Jack’s dead body as he drowns in the ocean still haunt the viewers and bring tears to eyes. Raising the bar of the disaster genre and exhibiting how true love never dies, Titanic never fails to indulge the audience in an emotional turmoil.

Earning more than $2 billion at the box office and setting new Academy Award records, the success of Titanic might never be replicated. Even after two decades since its release, the movie undoubtedly still stands out as the greatest saddest romantic movie ever made.


Did we miss any of the best saddest romantic movies of all time? Feel free to share your views in the comments below!