15 Movies That Are Great BECAUSE The Romantic Leads Don't End Up Together

Leonardo DiCaprio and Kate Winslet in Titanic

Who doesn't love a good romance movie? Those moments where the unsuspecting leads finally fall for each other always leave audiences with a warm, fuzzy feeling, and affirm our belief that true love does exist and can be found.

But not all romance movies have a happy ending. Sometimes, instead of the couple walking blissfully into the sunset, they walk away from each other in different directions. The next 15 movies on this list feature relationships that take a turn for the worse, leaving you tearing up and reaching for the tissue box.

For this list, we're picking our favorite movies that leave the audience in a puddle of tears. To qualify, the romantic leads cannot be together by the film's end. The movies in question can either be hilarious rom-coms or heart-pounding dramas, just as long as the film's leads don't wind up in a warm embrace.

Here are 15 Movies Where the Romantic Leads Don't End Up Together.


Continue scrolling to keep reading

Click the button below to start this article in quick view

Ryan Gosling and Emma Stone in La La Land
Start Now

15 La La Land

Ryan Gosling and Emma Stone in La La Land

For such an upbeat movie filled with catchy jazz songs and bright performances, La La Land doesn't have the happiest ending. Damian Chazelle’s love-letter to Los Angeles, the city where dreams are made, stars Ryan Gosling and Emma Stone as two struggling artists trying to make it in the entertainment biz. Gosling plays a jazz pianist, Sebastian, while Stone plays an aspiring actress, Mia. With some determination and a bit (or a lot) of luck, they find success in their respective fields, but it comes with a price.

The denouement of La La Land takes place in an epilogue five years after the main events of the film. We find that Mia has become a famous Hollywood actress, but it is revealed that she is no longer together with Sebastian. Mia and her new husband go to dinner one night and they wind up in Sebastian’s newly opened jazz club. In a lengthy dance number, Mia and Sebastian fantasize what life would have been like had they stayed together before they share one last longing look before parting ways forever.

14 (500) Days of Summer

Joseph Gordon Levitt and Zooey Deschenel in 500 Days of Summer

Marc Webb’s offbeat romantic comedy turned heads in 2009 for its unusual non-chronological storytelling and for its realistic ending which doesn’t see its two romantic stars happily walk off into the sunset. Joseph Gordon-Levitt plays Tom, a hopeless romantic who thinks he’s met the girl of his dreams in Summer, played by Zooey Dechanel. The film is told in a nonlinear fashion, flashing between all of the good times and all of the not so good times in Tom and Summer's romance.

Eventually, their relationship implodes and the two break up. After struggling through depression, Tom is shocked to learn that Summer is now engaged to be married. The ending has the two meet one last time as Summer admits to Tom that she was never in love with him. Tom is distraught that he has been wrong about true love all along, but Summer reassures him that his views on love were right, just not with her. While the pair don’t wind up together in the traditional sense, we see that Tom has learned something about expectations, and that hopefully his next relationship that is hinted at ends on a more positive note.

13 The Break-Up

Vince Vaughn and Jennifer Anniston in The Break-Up

While Peyton Reed’s romantic comedy The Break-Up follows the playbook of the genre, it makes up for it by providing a realistic and somber ending that reflects real-life breakups instead of the happy conclusions we’ve come to expect. Vince Vaughn and Jennifer Aniston play couple Gary and Brooke, who are both unsatisfied with the lack of commitment in their relationship. In a ploy to make him jealous, Brooke ends up dumping Gary. The plan has the opposite of the desired effect, and the two become vehement enemies while they each stay in their expensive condo.

After Gary comes to the realization that he has been selfish in their relationship, the two finally move on with their lives. Gary focuses more on his tour guide business, while Brooke travels the world. After some soul-seaching, the two cross paths by chance on a sidewalk and exchange in some pleasant yet awkward conversation. Instead of promising the audience that the two might get back together, both characters continue down the street after sharing one last smile to let each other know they're in a better place.

12 The Maltese Falcon

The Matlese Falcon

Directed and written by John Huston, The Maltese Falcon is one of cinema’s very best film noirs. It stars Humphrey Bogart as a hardboiled private eye, Sam Spade, who takes his latest case from a mysterious woman named Brigid O’Shaughnessy who is looking for her missing sister. Bogart’s detective soon becomes ensnared in a twisted plot that has involves several dangerous criminals all looking for a sought after statue called the Maltese Falcon.

The interweaving story comes to a head when it is revealed that Brigid was the one responsible for the death of Spade’s former partner to pin the crime on someone else. Brigid then confesses to Spade that she really loves him, and while Spade admits he has feelings for her too, he simply can’t trust her. The private eye ends up turning Brigid in to the police for the death of his partner. As a final condolence, Spade says that if they hang Brigid for murder he’ll always remember her, which is kind of romantic, we think.

11 Ghost

Demi Moore and Patrick Swayze in Ghost

Ghost may have one of the most iconic moments between two lovers with the whole pottery scene, but those warm, fuzzy feelings quickly dissolve when the movie kills the main character off in the first act. Patrick Swayze plays Sam, a man who is fatally shot while being mugged. Instead of his soul moving on to the afterlife, Sam remains on Earth as a ghost. He soon finds out that his death was no accident, and tries to solve his murder while protecting his true love Molly, played by Demi Moore.

After his killer gets what’s coming to him, Sam appears in his mortal form in front of Molly. Just when it looks like Sam’s life is about to be restored to him, he instead follows a bright light to what the viewer can only assume to be the afterlife, leaving Molly with one final goodbye. Although Sam and Molly don't get to spend their lives together, the underlying message of Ghost is that true love is eternal, even after death.

10 Blue Valentine

Ryan Gosling and MIchelle Williams in Blue Valentine

Based on its title, you may not be shocked to learn that Blue Valentine isn't a rom-com with a nice, fuzzy ending. Derek Cianfrance’s drama follows a contemporary married couple played by Ryan Gosling and Michelle Williams, charting their lives between different points in their relationship. The story skips around in time, showing how Gosling’s Dean and William’s Cindy fell in love, had a child, and eventually get divorced.

Coming from a broken home, Dean lets his depression get the better of him, which, ultimately, causes Cindy to get fired from her job. Cindy tells Dean that she wants a divorce, and would rather their daughter not grow up in a home with parents that hate each other. In the end, Dean and Cindy decide to part ways for the stability of their daughter. Though it may be hard to watch at times, Blue Valentine is a gripping and all too realistic portrayal of a marriage on the rocks that doesn’t sugarcoat its ending.

9 Edward Scissorhands

Johnny Depp in Edward Scissorhands

Stylized, gothic and surprisingly sentimental, Tim Burton didn’t pull any punches for his 1990 movie, Edward Scissorhands, which features one of the most sympathetic characters in one of the most heart-wrenching endings. Johnny Depp plays a gentle man with scissors for hands, who tries to fit in with a wholesome community after living in isolation for years. He forms a connection with Kim (Winona Ryder) who is kind towards Edward and his rather jarring disability.

Though Kim understands Edward, the rest of her community lashes out against him after a series of unfortunate mistakes, and Edward retreats back to his abandoned mansion. Though Kim reunites with Edward, they are followed by Kim’s jealous ex-boyfriend, Jim (Anthony Michael Hall). After Jim assaults Kim, Edward stabs him in the stomach and pushes him out of a window to his death.

Realizing it's impossible for them to be together, Edward and Kim share a final kiss before they say their final goodbyes. Though it might be disappointing to viewers that Edward and Kim don’t end up together, the movie's important message about inner beauty manage to shine through (as schmaltzy as that may sound).

8 Moulin Rouge!

Moulin Rouge

One part musical, one part drama and one part romance, Baz Luhrmann’s Moulin Rouge! stars Nicole Kidman and Ewan McGregor as a pair of young lovers in the turn of the 20th century. McGregor plays Christian, a young English poet who journeys to Paris to chronicle the Bohemian revolution. Once there, he visits the local hotspot, a club named Moulin Rouge, and falls for burlesque dancer, Satine. Unfortunately for Christian, Satine is already the object of affection of the club’s biggest patron, the Duke of Monroth, which causes a dangerous love triangle between the three.

The Duke finally threatens to kill Christian if Satine refuses to stop seeing him. Fearing for Christian’s life, Satine lies and tells him that she does not love him, until the climactic musical number in which she confesses her true feelings. Just when it looks like Christian and Satine will go on singing happily ever after, the curtain on their show closes, and Satine suddenly dies from tuberculosis. Though the movie's ending might be somewhat abrupt, it no doubt resonated with audiences, earning 8 Academy Award nominations in 2002.

7 Lost in Translation

Lost in Translation

Lost in Translation is a rare movie that shows the beauty in fleeting moments. Bob Harris is a fading movie star shooting a whiskey commercial in Japan. By chance, he crosses paths with Charlotte, a fellow American whose husband is a photographer on assignment in the same area. Lost in their current situations and feeling isolated in a foreign country, the two form an unlikely connection. They quickly become good friends, exploring the nightlife in Tokyo and helping each other with their feelings of loss.

Though Bob and Charlotte's relationship can be interpreted many different ways, it's been a burning question in audience's minds that under different circumstances, it might have blossomed into a romantic one. The two obviously share a strong bond, which makes it all the more painful when they realize their time in Tokyo must end. Though the two eventually part ways, we're left on a positive note as Bob whispers his emotional parting words into Charlotte's ear.

6 Brokeback Mountain

Heath Ledger and Jake Gyllenhaal in Brokeback Mountain

Winner of three Academy Awards (and robbed of Best Picture as some would say), Ang Lee's Brokeback Mountain is the story of a secret and forbidden love between two cowboys over the course of many years. Played by Jake Gyllenhaal and Heath Ledger, Jack and Ennis first meet on a job as sheep herders on Brokeback Mountain. Their relationship starts as a budding friendship, but after getting to know each other a little more, they strike up a blissful romance that lasts all summer. Though they each later settle down and become married, Jack and Ennis carry on their affair while hiding in secrecy.

As the audience eagerly awaits for the day the two cowboys will openly admit their love, that day never comes. Tragedy strikes by the end of the film when Jack's wife tells Ennis that Jack was accidentally killed while changing a tire. As Ennis hears this, thoughts of an angry, homophobic mob beating Jack to death flash across his mind. Though it's left as a mystery as to how Jack really met his fate, the message that one should never deny themselves true love resonates strongly by Brokeback Mountain's end.

5 Harold and Maude

Harold and Maude

As unconventional as a love story can get, Harold and Maude is a movie about the unlikely romance between 20-year-old Harold and 79-year-old Maude. Rich, depressed and obsessed with death, Harold spends most of his free time at funerals. At one of these funerals, Harold meets Maude, a  much older woman who has a unique, rich perspective on living. The two form a close relationship as Maude introduces Harold to art, music and living in the moment. Despite Harold's mother's many attempts of setting him up with potential wives, Harold makes the startling announcement that he is going to marry Maude, a woman more than 50 years his senior.

Their love is not meant to last however. On  her 80th birthday, Maude reveals to Harold that she has take a fatal dose of poison, ready to die after living a long, fulfilling life. Though Harold rushes Maude to the hospital, he is too late, and Maude dies shortly after. Though the audience is at first led to believe that Harold commits suicide, it is revealed that he has taken Maude's beliefs to heart, and happily sings a Cat Stevens tune on a banjo that reminds him of his lost love. It's an ending that is sad, but uplifting as it shows that death is just another part of life.

4 Titanic

Leonardo DiCaprio and Kate Winslett in Titanic

Of course, this list wouldn't be complete if it didn't include everyone's favorite doomed romance from Titanic. James Cameron's box office juggernaut from 1997 gained notoriety for its special effects, but what really kept audiences coming back for more was the romantic relationship between Leonardo DiCaprio's Jack and Kate Winslet's Rose.

The classic example of a forbidden romance, 17-year-old aristocrat Rose's life is changed when she falls for a poor but talented artist, Jack, while aboard the luxurious but ill-fated Titanic. It's the relationship that every viewer rooted for, but by the end had every viewer reaching for the tissue box. As the Titanic sinks in the North Atlantic Ocean, Jack sacrifices himself so Rose can remain on the one scrap of debris from the ship. Audiences have wondered for years if the door that Rose clung to was big enough to support both her and Jack, but then again, some romances are not built to last. At least we get that heartfelt ending in the afterlife where the lovers are reunited, which is a little odd considering Rose was married for a number of years after and raised a family.

3 Gone with the Wind

Gone with the WInd

Winner of eight Academy Awards, and still the longest film to date to win Best Picture, Gone with the Wind is an epic romance story set to the backdrop of the American Civil War. Vivien Leigh plays Scarlett O’Hara, a Southern belle who falls madly in love with outsider Rhett Butler, played by Clark Gable. After Scarlett turns Butler away on a number of occasions, she finally realizes that he is her one, true love. Unfortunately, it is also that moment that Butler realizes he’d rather live without Scarlett.

Gone with the Wind is a story that sees Scarlett second guess all of her romantic decisions, and only when she realizes she wants to be with the man she loves is it is too late. As Scarlett desperately clings to Butler and asks what she’ll do without him, Butler looks her straight in the eyes and utters the famous line, “Frankly, my dear, I don’t give a damn.” It was one of the first swears ever said on screen, and one of the earliest examples where the two leads don’t wind up happily ever after.

2 Annie Hall

Woody Allen and Diane Keaton in Annie Hall

Woody Allen has had one of the most successful and consistent careers in Hollywood, but for all his films, he will undoubtedly be remembered best for Annie Hall. The 1978 Best Picture winner stars Allen as Alvy, a neurotic comedian who reminisces on his newly demised relationship with the ditzy Annie Hall.

The narrative of Annie Hall plays with the flow of time, jumping between various points in Alvy’s life to discover why his relationship with Annie wasn’t meant to last. Unlike most of the entries on this list, we start the movie fully aware that their romance is doomed. Rather than use the formulaic structure of boy-meets-girl, boy-and-girl-get-together, boy-loses-girl and boy-gets girl-back, Allen depicts a realistic, nuanced story of how relationships function and how most times they don’t always work out. Though the director has stated that the movie didn’t turn out the way he planned (the romance was originally just going to be a side plot), Annie Hall is a significant piece of cinema that manages to avoid a cliché ending.

1 Casablanca

Casablanca Ending

One of the most iconic romance stories in one of the most influential film noirs, Casablanca tells the story of Rick Blaines, a cynical, exiled American running one the hottest cafes in Casablanca, Morocco during the early years of World War II. When Blaine comes into two transit letters of importance, he is visited by his old flame, Ilsa, who reveals that she is married to a political leader. When Ilsa tells Rick that she is still in love with him however, the two plan to run off using the letters of transit.

Unfortunately, things do not go as planned. While he is normally not a man to stick out of his neck for anybody, Rick uses the letters of transit for Ilsa and her husband to escape the country. While Ilsa protests, Rick tells her that she will regret it if she stays, "Maybe not today. Maybe not tomorrow, but soon and for the rest of your life." Although the final moments of Casablanca are heartbreaking, they remain as some of the most memorable in all of cinema, making this tearful goodbye our #1 pick for this list.

More in Lists