19 Romantic Films Where the Guy Doesn’t Get the Girl

In most romantic movies, the hero wins the heart of his beloved and they live happily ever after. But in this post, we’re highlighting 19 romantic films where the guy doesn’t get the girl, featuring bittersweet endings and unrequited love stories.

Gone with the Wind (1939)

Photo Credit: New Line Cinema.

In “Gone with the Wind,” Rhett Butler’s passionate pursuit of Scarlett O’Hara ends in disappointment as she remains fixated on another man. Rhett’s famous parting line, “Frankly, my dear, I don’t give a damn,” is the climax of a tragic, unrequited love.

(500) Days of Summer (2009)

Photo Credit: Fox Searchlight Pictures.

“500 Days of Summer” unravels Tom’s infatuation with Summer, who insists on keeping their relationship casual. The film’s non-linear narrative leads to an emotional climax, with Tom heartbroken but finally learning to move on.

My Best Friend’s Wedding (1997)

Photo Credit: TriStar Pictures.

In this romantic comedy, Julianne (Julia Roberts) realizes she’s in love with her best friend Michael (Dermot Mulroney) just as he’s about to marry someone else. Her attempts to win him over fail, teaching her a tough lesson about love and friendship.

La La Land (2016)

Photo Credit: Lionsgate.

“La La Land” presents the love story of two artists who are torn between their dreams and their relationship. The heart-rending ending sees them part ways to pursue their individual dreams, making this a beautiful but bittersweet romantic film.

The Remains of the Day (1993)

Photo Credit: Columbia Pictures.

This profoundly moving film follows a dutiful butler, Mr. Stevens (Anthony Hopkins), who represses his feelings for the housekeeper, Miss Kenton (Emma Thompson). Their love story remains unfulfilled, leading to a poignant finale.

Titanic (1997)

Photo Credit: Paramount Pictures.

“Titanic” is a tragic love story between Jack (Leonardo DiCaprio) and Rose (Kate Winslet) set against the backdrop of the infamous ship’s sinking. Despite their intense love, Jack dies, leaving Rose with only memories.

Romeo + Juliet (1996)

Photo Credit: 20th Century Fox.

Baz Luhrmann’s “Romeo + Juliet” breathes new life into the classic Shakespearean tragedy. Despite their profound love, both Romeo (Leonardo DiCaprio) and Juliet (Claire Danes) meet a tragic end.

Brokeback Mountain (2005)

Photo Credit: Focus Features.

“Brokeback Mountain” explores the forbidden love between two cowboys, Ennis (Heath Ledger) and Jack (Jake Gyllenhaal). Social constraints force Ennis into a loveless marriage, leaving Jack alone and heartbroken.

Casablanca (1942)

Photo Credit: Warner Bros.

“Casablanca” sees Rick (Humphrey Bogart) sacrifice his love for Ilsa (Ingrid Bergman) for the greater good during World War II. His poignant decision leads to one of the most iconic farewells in film history.

Blue Valentine (2010)

Blue Valentine _ Hunting Lane Films. Silverwood Films
Photo Credit: Hunting Lane Films/Silverwood Films.

“Blue Valentine” juxtaposes the sweet beginnings and bitter end of a relationship between Dean (Ryan Gosling) and Cindy (Michelle Williams). The marriage crumbles, and Dean’s hope for reconciliation with Cindy shatters.

Lost in Translation (2003)

Photo Credit: Focus Features.

“Lost in Translation” captures the transient bond between Bob (Bill Murray) and Charlotte (Scarlett Johansson), who meet in Tokyo. They part ways, carrying with them a memory of a relationship that could have been.

The Age of Innocence (1993)

Photo Credit: Columbia Pictures.

In Martin Scorsese’s “The Age of Innocence,” Newland (Daniel Day-Lewis) is caught in a love triangle. Bound by societal norms, he marries May (Winona Ryder) but longs for Countess Olenska (Michelle Pfeiffer).

In the Mood for Love (2000)

Photo Credit: Jet Tone Productions/Paradis Films.

“In the Mood for Love” is a slow-burning tale of unrequited love between neighbors who discover their spouses are having an affair. Their mutual attraction remains unconsummated, leading to a melancholic ending.

Doctor Zhivago (1965)

Photo Credit: MGM.

“Doctor Zhivago” portrays a tumultuous romance between Yuri (Omar Sharif) and Lara (Julie Christie), set during the Russian Revolution. They are separated by the socio-political upheaval, leaving Yuri heartbroken.

Brief Encounter (1945)

Photo Credit: Eagle-Lion Distributors.

“Brief Encounter” tells the story of Laura (Celia Johnson) and Alec (Trevor Howard), who meet at a train station and fall in love, despite being married to other people. Their relationship ends abruptly, with Alec moving to South Africa.

A Star Is Born (2018)

Photo Credit: Warner Bros.

In “A Star Is Born,” Jack (Bradley Cooper) helps Ally’s (Lady Gaga) singing career take off, but their romance is hampered by his addiction. The film ends in tragedy, leaving Ally alone with their music.

The Curious Case of Benjamin Button (2008)

Photo Credit: Paramount Pictures.

“The Curious Case of Benjamin Button” presents a unique love story of a man aging in reverse. Despite his deep love for Daisy, Benjamin chooses to leave to spare her the pain of watching him turn into a child.

Moulin Rouge! (2001)

Photo Credit: 20th Century Fox.

“Moulin Rouge!” is a musical spectacle centered around a tragic romance between a courtesan and a penniless writer. Satine’s (Nicole Kidman) untimely death leaves Christian (Ewan McGregor) with only memories of their brief yet passionate love affair.

The English Patient (1996)

Photo Credit: Miramax.

“The English Patient” weaves a complex tale of a doomed love affair during World War II. Count Almásy’s (Ralph Fiennes) love for Katharine (Kristin Scott Thomas) remains unrequited as they’re separated by the war, leading to a heart-wrenching finale.