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14 Romantic Movies Where They Don’t End Up Together
14 Romantic Movies Where They Don’t End Up Together
Entertainment | February 11, 2021
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Just in time for Valentine’s Day, consider this list of romantic movies your must-watch. Unlike the typical, however, these films don’t end in a happy ending.

As of the last census, the number of single Filipinos amount to 34.8 million. So, that just means not everyone will have someone to celebrate Valentine’s Day with. Many will probably just choose to stay home and watch a movie–a romantic movie. But not of the “happy ending” variety.

Personally, the romantic movies I remember the most are the ones that didn’t end happily, or
movies where the two romantic leads don’t end up together. I think it’s because the human psyche remembers pain more than happiness. Am I wrong here? Go, fight me.

In any case, I have curated 14 of the most memorable romantic movies where the lovers don’t end up together.

14. Titanic (1997)

A modern classic, who can forget this epic, tragic love story between a 17-year-old first-class passenger on the RMS Titanic, Rose DeWitt Bukater (Kate Winslet), and a poor artist below deck, Jack Dawson (Leonardo DiCaprio)? The ultimate rich girl falls for poor boy story, with the odds ever against them. I mean their meet cute is attempted suicide and alleged rape, super dark–those alone foreshadow the fate of the two star-crossed lovers on the ill-fated ship, the most famous in history.

Set in the backdrop of a historical event, these fictional characters are crafted so realistically, you fall in love with them in their three-day journey into open sea. Makes us all feel that in love, there is no class or tragedy too great, love overcomes.

Of course in the end, Jack makes the ultimate sacrifice and saves Rose “in every way a person can be saved.”

The saddest line in the movie is when an aged Rose says, “I don’t even have a picture of him. He exists only in my memory…”

13. La La Land (2016)

One of the saddest musicals I’ve seen–two dreamers set in the backdrop of where most love stories are made, Hollywood. A favorite to win the Oscar Best Picture, mistakenly announced as the winner, but nevertheless, a pioneer in “revisionist” endings.

Stereotypical waitress slash aspiring actress Mia Dolan (Emma Stone)’s meet cute with struggling Jazz pianist Sebastian Wilder (Ryan Gosling) was a moment of road rage in traffic on a freeway–how wonderfully L.A., right? Right.

This comes after an elaborately choreographed opening scene where an entire freeway breaks into song and dance. The tone of the entire movie is generally joyous as the couple foray into personal and professional failure before their dreams come true. I guess this is what every L.A.-based love story is about–humbly dreaming big dreams with someone you love and seeing those dreams eventually come true but lose that someone you love.

The saddest part about this multiple Oscar-nominated movie isn’t the ending, it’s the alternate ending director Damien Chazelle poses alongside with it.

When Mia sees the neon light of Seb’s name, it makes you think of all the love you once had for someone and how it ended. And that the saddest of all feelings is finding success apart.

12. One Day (2011)

There’s something so sweeping about a movie that tells a love story that spans many years. This one follows college friends Dexter Mayhew (Jim Sturgess) and Emma Morley (Anne Hathaway) from their graduation from university to their individual careers. She sets out to be a writer but
ends up a waitress in a Mexican restaurant while his career takes off.

Despite their mutual attractions, Emma turns down Dexter’s advances because she doesn’t want to lose him as a friend. And through the years, as her career slowly begins to pick up and is offered a book deal, his comes crashing down. He marries another and becomes a father.

Years later, as they continue to rekindle their friendship, Dexter finds out that Emma has been in love with him since college and makes a move to make her finally his. When they begin a relationship, all the possibility of the years ahead compounded only by the years they waited to be together ends when she suddenly and tragically dies.

Makes you think that while love waits, sometimes it’s better to love early and to love now.

11. Shakespeare In Love (1998)

A depiction of a fictional love affair between famed, historical playwright William Shakespeare (Joseph Fiennes) and Viola de Lesseps (Gwyneth Paltrow) during the time he was writing Romeo and Juliet.

A working playwright, Will suffers from writer’s block in writing a new comedy (a happy
ending). He seeks inspiration from Rosaline only to find out she was bedding another. Crushed, Will sets out to use his pain for pages in his new play. Things change when a boy, Master Thomas Kent, who is actually Viola disguised as a man reads his words from another play of his. He is intrigued and enamored and questions his attraction only to find out later on that Master Kent is actually Viola.

He pursues her and she inspires him to write and their secret love affair births the greatest play in history.

This comedy ends with the two lovers parted by a shipwreck and Viola is presumed dead but is seen walking eternal sands only to be fictionally immortalized in “Twelfth Night,” another of Shakespeare’s plays.

10. Romeo + Juliet (1996)

An American spin of the most infamous Shakespearean classic, helmed by a Mexican director, and starring the greatest movie star of the 90s, Leonardo DiCaprio as the ill-fated Romeo and Claire Danes as her Juliet.

Rewatching this now on Netflix, it still feels current and relevant with the conflict of two children of rival families fall in love with each other. Fair Verona becomes Verona Beach and the rivalry becomes gang wars. The visuals, the costumes and the very modern soundtrack all come together to give you a visceral experience of young love in its rawest form, love at first sight, sex on the second date and marriage on the third.

You are taken on a spin. But just as high as you go, the faster falling down is. The glaring difference in this adaptation and the saddest also is that Romeo awakens nanoseconds before Juliet dies–they see each other briefly before they both meet their tragic end.

9. Atonement (2007)

The sound of the typewriter opens this movie telling a story that is written with an emotion maybe as powerful as love–guilt. Once again a tale of “Rich Girl” falls for “Poor Boy,” the young romance of Cecilia (Keira Knightley) and the housekeeper’s son Robbie (James McAvoy) is thwarted by unexpected circumstances and extraordinary injustices–it is the right love at the worst possible time.

A love that could have been saved by the brilliance of the truth. This movie only goes to show that the bad things that happen to us greatly affect the way we are able to love. And it’s sad really when a pure love is tainted by some of the gruesome experiences that can happen to a human being.

The saddest part is that in the end, no amount of revisionism can atone for the sins of the past. Not even love could save it.

8. Ghost (1990)

I remember watching this movie on laser disc because I was too young to watch it in the cinema. It was a generation-defining movie that spawned a hairstyle trend that almost all women sported, including my mom.

Up until this movie, being in love with a ghost seemed hardly romantic. But the very modern take in relationships to tell the story of banker Sam Wheat (Patrick Swayze) and his sculptor girlfriend Molly Jensen (Demi Moore) was truly refreshing.

They had code words for “I Love You” and an enviable life together–a young successful couple living in New York only to be victimized by the streets of New York.

Together, they realize and discover the transcendent power of love. That you take the love in your heart with you even after you die. And that is both infinitely sad and fiercely hopeful. That’s ditto forever.

7. Closer (2004)

Do we really ever get to know the person we fall in love with? As close as we get to them, do we ever really know who they are?

This movie with the powerhouse cast of Julia Roberts, Jude Law, Natalie Portman, and Clive Owen is an intertwining love story of two couples, four individuals ruined forever by a single indiscretion.

Dan (Jude Law) commits and indiscretion with a photographer named Anna (Julia Roberts) when she takes his portrait. This incident makes Dan realize he is in love with her and not with his stripper girlfriend Alice (Natalie Portman). He pursues Anna while he is with Alice, meanwhile, Larry (Clive Owen), finding out about his wife Anna’s infidelity, seeks Alice to exact
revenge on Dan.

In the end, Dan loses both Anna and Alice setting Alice free from the lie she has been living. The very poignant scene at the end makes you think about the things we keep secret from our lovers no matter how deeply we are in love with them.

6. Call Me By Your Name (2017)

What is it about falling in love with someone in the summertime that makes it feel more fleeting thus makes it more consuming, the ardent longing for someone we meet once, and then never again.

Okay, so before Armie Hammer was revealed to be a kinky cannibal, he was Oliver in this Luca Guadagnino modern classic. A 24-year-old graduate student spending the summer in rural Northern Italy as assistant to Elio (Timothée Chalamet). At 17, Elio is only beginning to come into his sexuality and his experiences with his girlfriend doesn’t quench the heat of the desire in his body. But as the summer drags on, he discovers Oliver is the one to put out all of his fire. Oliver pursues him and they take on this new and exciting awakening together.

Privately aware of their love, Elio’s father acknowledges its legitimacy even as the two lovers were confused by it. In the end, heartbreak becomes the reward of being true to oneself.

But they could always call each other by their names.

5. Love Story (1970)

The classic romantic American drama features the stunning good looks of Ryan O’Neal and Ali MacGraw.

The heir of an upper-class East Coast family attends Harvard University where he is also a hockey player. He meets a working class, whip smart Radcliffe College student of classical music. Despite their differences, rich boy falls for poor girl and get married.

This disobedience causes Oliver (O’Neal) to lose his family’s financial support and together with his new wife Jenny (MacGraw) struggle to pay his way through Harvard Law. Everything is well and good until doctors tell Oliver that Jenny is terminally ill.

As Jenny’s health fails, Oliver returns to his wealthy family to ask for money to help her with her treatment. His father simply writes him a check but ultimately Jenny dies.

4. The Way We Were (1973)

Referenced on “Sex and the City,” “The Way We Were” pays tribute to the “Wil,”untamable woman. Legends Barbra Streisand and Robert Redford play Katie Morosky and Hubbell Gardiner. Their differences are glaring from the get go–she’s a Marxist Jew with very strong convictions while he’s a carefree Protestant with really no political inclinations.

He is intrigued by her, fascinated while she is charmed and captivated by his pretty boy looks. She calls him “Preppy,” her Preppy.

He eventually becomes a successful screenwriter while she feels enclosed by their affluent lifestyle–the very encroachment to her political activism.

In the end, Katie’s strong alpha persona emasculates Hubbell and he retreats into the arms of an old college girlfriend who, like him, comes from privilege.

Katie and Hubbell get a divorce and meet years later at New York’s iconic Plaza Hotel where she sees him with a woman that was much more suited for him. He acknowledges her and she walks away.

3. Amour (2012)

The very poignant French film that focuses on an elderly couple as they navigate through the daily struggle of paralysis starring Emannuelle Riva who is the oldest Oscar Best Actress nominee at 85 for this role and Jean-Louis Trintignant who plays her devoted husband.

The live in an old apartment in Paris as retired piano teachers but as old age ravages them, the true test of their relationship begins. When she suffers from a stroke that leaves her in a wheelchair, he waits on her, serves her hand and foot. When their daughter suggests that they commit her into professional care, he dismisses the idea and continues to look after his wife.

But as time passes and Anne (Riva) finds it harder and harder to hold on, Georges (Trintignant) gives into her wishes–he smothers her.

2. Blue Valentine (2010)

For me the saddest movie on this list, Michelle Williams (Cindy) and Ryan Gosling (Dean) give very poignant, powerhouse performances that leave a gaping hole in the heart.

Dean is a hopeless romantic high school dropout while Cindy is an ambitious pre-med student with aspirations of becoming a doctor. Two unexpected encounters later, Cindy finally gives in to Dean’s persistence and goes on a date with him Ironically, their relationship begins with a
sidewalk dance that is the saddest, most romantic thing you have ever seen.

The two get married and struggle in live in rural Pennsylvania. Her life with him makes Cindy realize that she has made the mistake of her life in marrying him and that she is no longer in love with him and trapped in the relationship. While he, still very madly in love with her, try his best to make her happy with him. But the more he pushes, the more she retreats.

Ultimately, she demands for a divorce as you see a very broken poor man walking away still very much in love with her.

1. Prime (2005)

My most favorite romantic comedy movie of all time. It presupposes that men and women reach their sexual prime at different ages–men in their twenties, women in their thirties.

Uma Thurman plays Rafi, a 37-year-old Manhattanite careerwoman divorcee who meets a talented 23-year-old painter David, played by Bryan Greenberg, at the movies when both their dates sucked. Their meet cute is when they are trapped in the restroom together and the physical attraction just becomes so palpable.

He pursues her, a successful woman 15 years his senior and she accepts him upon the advice of her therapist who, unbeknownst to all of them is the mother of David. She, of course, is played by Meryl Streep.

The love affair is strong and undeniable and as their relationship deepens, Rafi realizes that what she wants most in life is to have a child and she could not possibly ask it from David who is just starting to live his life. They both make sacrifices but ultimately sacrifice themselves for each other.

They separate while still very much in love.

This movie makes a very strong, practical and realistic case against dating way above or below your age range eventhough you are both at the prime of your life.

G3 San Diego is a Filipina writer, an entertainment journalist, a key opinion leader, an online talk show host, a third-generation farmer, and a modern-day romantic.
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