September 20, 2024 | Sarah Ng

The Most Upsetting Romance Movies Of All Time


Sometimes You Need A Good Tearjerker

Do you ever get in that funny mood where you think: "I'd like to be emotionally destroyed today". Well, grab your tissues because these upsetting romance movies are just the ticket.

Upsetting-Romance-Msn

Moulin Rouge (2001)

Baz Luhrmann's Moulin Rouge might be exactly what you're craving if you're looking for a musical romance that will absolutely wreck you. The film follows two star-crossed lovers: a poet named Christian, played by Ewan McGregor, and a courtesan named Satine, played by Nicole Kidman. 

Buckle up, because this glittery rollercoaster only ends in tears.

A snapshot of the movie Moulin Rouge!Bazmark Productions, Moulin Rouge! (2001)

Moulin Rouge (2001)

What makes Moulin Rouge such a tearjerker? Well, it must be the stark contrast between the fantasy of the cabaret and the sad truth of both of our protagonists' lives. Behind the scenes, Satine is slowly dying—unbeknownst to her true love, Christian. 

Though she seems to be the picture of beauty and health, Satine longs for a better life—and we, the audience, are rooting for her to escape the Moulin Rouge.

A snapshot of the movie Moulin RougeBazmark Productions, Moulin Rouge (2001)

Moulin Rouge (2001)

As Satine and Christian embark on a forbidden love affair, external forces and villains attempt to break them apart. The film builds towards a feel-good climax—only to rip it away within seconds. 

When the curtains close, you'll be left with one resounding message: "The greatest thing you'll ever learn is just to love and be loved in return".

A snapshot of the movie Moulin RougeBazmark Productions, Moulin Rouge (2001)

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The Painted Veil (2006)

An extremely underrated period romance has to be 2006's The Painted Veilstarring Edward Norton and Naomi Watts. This plot is just wild, and in the beginning, both of our romantic leads aren't the most likable characters. But herein lies the magic of this movie. By the end, you will love both of them with every fiber of your being.

A screenshot of the movie The Painted VeilThe Mark Gordon Company, The Painted Veil (2006)

The Painted Veil (2006)

You see, Norton plays Charles, a bacteriologist whose wife Kitty cheats on him. Within this broken marriage, no love remains—that is, until Charles drags prim-and-proper Kitty into the middle of a cholera epidemic in China. Here, he helps treat victims of the disease and improve living conditions for the locals. 

This is when the dynamic between husband and wife begins to change.

A screenshot of the movie The Painted VeilThe Mark Gordon Company, The Painted Veil (2006)

The Painted Veil (2006)

In the midst of so much pain and suffering, Charles and Kitty get a second chance at love—and it's utterly heartwarming. Each begins to see one another in new ways and a fresh romance blossoms. 

It's a classic enemies-to-lovers trope—but instead of getting a much-deserved "happily ever after," we get one of the most devastating endings imaginable.

A screenshot of the movie The Painted VeilThe Mark Gordon Company, The Painted Veil (2006)

A Star Is Born (2018)

Bradley Cooper and Lady Gaga really did a number on our hearts with their performances in 2018's remake of A Star is BornIt follows the turbulent life of a famous country rock star named Jackson and an unknown singer-songwriter named Ally.

A screenshot of the movie A Star Is BornWarner Bros, A Star Is Born (2018)

A Star Is Born (2018)

When Jackson and Ally's very different worlds collide, sparks fly. The two have unbelievable chemistry, and his success helps Ally's music career catapult to great heights—a star is born. However, Jackson's demons and his struggle with addiction are the tragic undercurrents of the entire film.

A screenshot of the movie A Star Is BornWarner Bros, A Star Is Born (2018)

A Star Is Born (2018)

As Ally continues to shine in the spotlight, Jackson's life descends into darkness—and not even his love for Ally can save him. As gorgeous as the music in the movie is and as tender as the characters' beginnings are, the horrifying ending will likely turn you into a blubbering mess.

A screenshot of the movie A Star Is BornWarner Bros, A Star Is Born (2018)

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La La Land (2016)

2016's La La Landstarring Ryan Gosling and Emma Stone, is a musical that hits every note. Its feel-good and comedic trajectory leads to a very bittersweet ending that will have you questioning over and over again, "What if? What IF?"

A screenshot of the movie La La LandSummit Entertainment, La La Land (2016)

La La Land (2016)

Gosling plays a jazz pianist named Sebastian and Stone plays an actress named Mia. Both are struggling artists in the big bad world that is Los Angeles. As they both reach for their dreams, they fall deeper and deeper in love. However, as the film progresses, they get blindsided by a harsh dose of reality.

A screenshot of the movie La La LandSummit Entertainment, La La Land (2016)

La La Land (2016)

When it comes to making their relationship work, Sebastian and Mia have to make a very important decision—one that will alter their lives forever. The closing montage of this movie is where tears will inevitably fall. It's the perfect way to wrap up this wistful love story.

A screenshot of the movie La La LandSummit Entertainment, La La Land (2016)

PS I Love You (2007)

Romance films cut the deepest when they refuse to shy away from the hard parts of life. 2007's PS I Love Youstarring Hilary Swank and Gerard Butler, has this in spades. You get hit with the film's integral tragedy right at the beginning. 

A screenshot of the movie P.S. I Love YouAlcon Entertainment, P.S. I Love You (2007)

PS I Love You (2007)

Gerry, who passes from a brain tumor, leaves behind his grieving wife Holly. However, he's left something behind for her—a series of encouraging messages that all end with, you guessed it, "PS I Love You".

A screenshot of the movie P.S. I Love YouAlcon Entertainment, P.S. I Love You (2007)

PS I Love You (2007)

This romance is about remembering those we've lost, but also about the importance of grieving and moving forward. Gerry doesn't want Holly to miss out on the rest of her life, and her attempt to find joy in new places is a testament to her love for her late husband. 

This movie might also make you cling to your partner even tighter. Tomorrow isn't promised, and all we have is time.

A screenshot of the movie P.S. I Love YouAlcon Entertainment, P.S. I Love You (2007)

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One Day (2011)

I remember going to the theaters in 2011 to see One DayI went in blind, just knowing that this movie promised to be an epic romance. Little did I know, I would leave as a husk of myself—absolutely wrecked by this movie's utterly unfair ending.

A screenshot of the movie One DayFilm4 Productions, One Day (2011)

One Day (2011)

For one, this movie was right up my alley: A nerdy girl and a bad boy develop a deep friendship that spans almost two decades, but they also have oodles and oodles of romantic tension. I was seated. I had my popcorn. I was grinning ear to ear... until I was not.

A screenshot of the movie One DayFilm4 Productions, One Day (2011)

One Day (2011)

The film's two main characters, Dexter and Emma, navigate their unrequited love and their own troubled lives, breaking apart and reuniting in delightful little twists throughout. However, just when you've let out a cheer of relief as their story draws to its inevitable end, the unthinkable happens—and it is not okay.

A screenshot of the movie One DayFilm4 Productions, One Day (2011)

Past Lives (2023)

Past Livesstarring Greta Lee, Teo Yoo, and John Magaro, was my favorite romance of 2023. It was the directorial debut of Celine Song, and the fact that her real life inspired the story makes it all the more moving.

A screenshot of the movie Past LivesA24, Past Lives (2023)

Past Lives (2023)

The film begins with a friendship between two 12-year-olds in South Korea: Na Young and Hae Sung. However, their lives diverge when Na Young and her family move to Toronto. Here, she changes her name to Nora. However, the two friends are destined to meet again.

A screenshot of the movie Past LivesA24, Past Lives (2023)

Past Lives (2023)

Though Nora and Hae Sung reconnect over Facebook as adults, the physical distance between them prevents them from ever pursuing their romantic feelings for one another. After losing touch for a second time, their lives propel them in opposite directions. But their story isn't over yet.

A screenshot of the movie Past LivesA24, Past Lives (2023)

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Past Lives (2023)

In the third act, these star-crossed characters come together for the last time—and this is where the scenes begin to pluck the audiences' heartstrings with reckless abandon. How do we reckon with the choices we've made, and grapple with the idea of what could have been? Have we known our loved ones in past lives? And if the lines get crossed, do we get a second chance in our next life?

A screenshot of the movie Past LivesA24, Past Lives (2023)

Call Me By Your Name (2017)

Do you remember what it was like to fall in love for the first time? 2017's Call Me by Your Name will not only transport you to the most idealistic version of Northern Italy in the 1980s, but might also dredge up memories of the naivety of youth.

A screenshot of the movie Call Me By Your NameFrenesy Film, Call Me By Your Name (2017)

Call Me By Your Name (2017)

Based on the novel by André Aciman, Call Me by Your Name follows the love story of a young man named Elio and an older graduate student named Oliver. This coming-of-age film lays bare the awkward and vulnerable moments that come along with the pangs of first love. But like most first loves, this story is headed for real heartache.

A screenshot of the movie Call Me By Your NameFrenesy Film, Call Me By Your Name (2017)

Call Me By Your Name (2017)

This stunning slow burn will eventually lead you to a haunting monologue delivered by Michael Stuhlbarg, who plays Elio's father. 

So much goes unspoken in this movie—but as the final scene draws to a close (with Sufjan Stevens's "Visions of Gideon" playing in the background), Elio will be crying, and most likely, you will be crying too.

A screenshot of the movie Call Me By Your NameFrenesy Film, Call Me By Your Name (2017)

Never Let Me Go (2010)

2010's Never Let Me Go—starring Carey Mulligan, Keira Knightley, and Andrew Garfield—tells the story of a doomed love triangle in a chilling dystopian world.

A screenshot of the movie Never Let Me GoDNA Films, Never Let Me Go (2010)

Never Let Me Go (2010)

The film follows the lives of three characters, beginning with their childhoods at a boarding school to their horrifying adult "occupations". Kathy fosters a deep love for Tommy, who winds up dating Ruth. 

However, in the end, no character has true control over their ultimate destiny, which makes the story such a tragedy.

A screenshot of the movie Never Let Me GoDNA Films, Never Let Me Go (2010)

Never Let Me Go (2010)

There's a dark twist in this film as we discover the nefarious truth about the overarching system these characters are slotted into. The conviction that Kathy, Tommy, and Ruth have in their feelings, as well as their great capacity for love, is what will stick with viewers long after the credits have rolled on by.

A screenshot of the movie Never Let Me GoDNA Films, Never Let Me Go (2010)

Atonement (2007)

2007's Atonement is probably the most frustrating film on this list. This stunning period piece, starring James McAvoy and Keira Knightley, follows the doomed romance of Robbie and Cecilia. 

After finally acting on their long-kept feelings for one another, the romantic leads are torn apart by an accusation made by Cecilia's little sister, Briony.

A screenshot of the movie AtonementUniversal Pictures, Atonement (2007)

Atonement (2007)

Briony falsely accuses Robbie of a heinous act, thereby destroying her sister's life, as well as her own. In the second act, Briony has to face the consequences of her actions and tries to atone for her mistake.

A screenshot of the movie AtonementUniversal Pictures, Atonement (2007)

Atonement (2007)

As the fates of all three characters unravel before our eyes, we are desperately hoping for Robbie and Cecilia to win back the happiness they so deserve. The tragedy of this story hinges on a single moment and reminds us that our lives can change in the blink of an eye—for better or for worse.

A screenshot of the movie AtonementUniversal Pictures, Atonement (2007)

The Bridges Of Madison County (1995)

I don't think I'll ever forget the first time I watched The Bridges of Madison Countystarring Meryl Streep and Clint Eastwood. It's such a quiet and warm film that shines with a hint of desperation.

A screenshot of the movie The Bridges Of Madison CountyAmblin Entertainment, The Bridges Of Madison County (1995)

The Bridges Of Madison County (1995)

The film follows a housewife who has a brief and passionate affair with a photojournalist while her family is away. It only takes four days for our main character Francesca to fall in love with Robert Kinkaid, with whom she shares a magnetic chemistry. However, reality eventually crashes in on them.

A screenshot of the movie The Bridges Of Madison CountyAmblin Entertainment, The Bridges Of Madison County (1995)

The Bridges Of Madison County (1995)

In the end, Francesca has to weigh the love she has for her family against the power of finding her one true love at the wrong time. This film will definitely strike a chord if you've ever experienced a fleeting love—one that still flashes across your mind from time to time, and makes you smile. 

If you didn't ugly cry by the end of this movie, I don't believe you.

A screenshot of the movie The Bridges of Madison CountyAmblin Entertainment, The Bridges Of Madison County (1995)

The Notebook (2004)

Would any romance list be complete without mentioning 2004's The Notebook? There's nothing quite like following the story of Noah and Allie, who first meet during a golden summer in the 1940s—only to be torn apart by the harsh realities of their different social classes. But that's not the most tragic part.

A screenshot of the movie The NotebookNew Line Cinema, The Notebook (2004)

The Notebook (2004)

The film expertly weaves together two timelines, showcasing the couple's youth and their elderly selves. It doesn't shy away from the dark truth of every romance—that all love stories must come to an end. 

A screenshot of the movie The NotebookNew Line Cinema, The Notebook (2004)

The Notebook (2004)

As their life together draws to a close, Noah and Allie grapple with their failing health and the fear of losing one another. The Notebook is all about the power of nostalgia and memory, proving that true love perseveres even in the most harrowing moments—even when our time runs out. 

If you've seen this film, you know that the heart-wrenching end will have you reaching for all the tissues.

A screenshot of the movie The NotebookNew Line Cinema, The Notebook (2004)

Titanic (1997)

When I was little, my mother had the box set of Titanic on VHS. There were two tapes, but she only ever let me watch the first one. For years, I had no clue that Rose and Jack had anything other than their much-deserved "happily ever after"... that is, until I grew up and watched the second tape for the very first time. 

A screenshot of the movie TitanicParamount Pictures, Titanic (1997)

Titanic (1997)

This love story makes the audience fall head over heels for the two leads, played by Kate Winslet and Leonardo DiCaprio. This, of course, ensures that the brutal ending is unbearably painful. However, few know that the film almost had an alternate ending.

A screenshot of the movie TitanicParamount Pictures, Titanic (1997)

Titanic (1997)

Don't get too excited—the alternate ending did not reverse the consequences of that infamous door scene. However, if it had been used, it would have absolutely destroyed the soft pacing of the film's conclusion. 

A screenshot of the movie TitanicParamount Pictures, Titanic (1997)

Titanic (1997)

You see, in the alternate ending, the scene where Rose throws her necklace into the ocean is very different. Brock and Lizzy find her by the ship's railing and think she's about to take her own life. 

Unlike the final cut, Rose shows Brock the necklace he's been searching for and even lets him touch it before she chucks it into the ocean anyway. 

It doesn't sound that different, but if you've seen that alternate ending then you know the right decision was made.

A screenshot of the movie TitanicParamount Pictures, Titanic (1997)


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