They say that art imitates life, and life is far from perfect. So it only makes sense that every movie doesn’t have a “happily ever after.” Some are even downright depressing. But such is life, right?

Some of the greatest romantic movies (and some that aren’t so great) actually involve a leading lad and lady who don’t run off into the sunset together. Plenty such films involve the death of one of the characters, evoking the “til death do us part” clause. But these movies involve couples who don’t end up together for reasons other than death — where it’s an insurmountable age difference, new (or old) love interests swooping in, bad timing, or just life getting in the way.

17. Little Black Book

It’s rare that snooping in someone you love’s personal things ever turns out well, and this movie is no exception. Stacy Holt thinks she’s with The One, but he can’t seem to fully commit. Thus, with some encouragement from her friend/coworker, she finds his ex-girlfriends in his Palm Pilot (LOL) and proceeds to set up in-person meetings with all of them to find out what they’re like. Don’t worry, it gets creepier.
The friend/coworker brings them all together on live television for a talk show and, clearly, Stacy and her boyfriend are furious. It was a crappy move for her coworker to pull, but it was also pretty terrible of her to go behind her boyfriend’s back in the first place. Then Stacy realizes the her boo is better off with one of his exes. You think there might be a happy romantic ending when she runs into her college sweetheart, but alas, he’s happily married. Fortunately, Stacy ends up with her dream job, so wasn’t it all worth it in the end? (Rest in peace Brittany Murphy.)

16. The Break-up

Watching the pure immaturity of Gary Grobowski and the levels Brooke Meyers stoops to in this movie can be painful at times. Breaking up with a partner that you live with when neither of you is able to immediately move out must be incredibly stressful, though surely each party could have handled the situation with more aplomb. In time, both of them end up getting their shit together and Gary even makes a romantic gesture to win Brooke back, but it falls short and they go their separate ways. Of course, the movie ends with them running into each other on the street and sharing friendly greetings, but there’s no true indication that they end up together again.

15. (500) Days of Summer

Although “manic pixie dream girl” wasn’t coined for Summer Finn in this movie, it might as well have been. The hopeless romantic male falls in love with the quirky girl who doesn’t believe in love, and shocking no one but him, it doesn’t end well. Although he loved her, Tom Hansen had Summer on a pedestal throughout their entire relationship, and still fails to recognize this after their breakup. When he tries to rekindle the romance at a party after the breakup, he finds out Summer is actually engaged. He doesn’t get the girl, but there is hope; the movie ends with him asking out a girl named *drum roll* Autumn.

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14. Gone with the Wind

Talk about a whirlwind romance. Scarlett O’Hara loves Ashley, but Ashley marries his cousin; Rhett loves Scarlett, but Scarlett turns him down; Scarlett marries Frank, but Frank dies; Scarlett marries Rhett, but claims to still love Ashley; Ashley and Scarlett cavort, but Ashley loves his wife; Scarlett finally realizes she loves Rhett, but their daughter has died and Rhett leaves her. Is there any more chilling a line to deliver to your distraught former lover pleading with you than, “Frankly, my dear, I don’t give a damn”? I think not. Issues of slavery and sexism and abuse notwithstanding, this is quite the classic.

13. The Lifeguard

Sometimes we’re sad when the leading lad and lady don’t end up together but in the case of The Lifeguard, THANK GOODNESS. Leigh London is a 30-year-old journalist (or rather, 29, as she reminds other characters throughout the movie) who leaves New York City to move back in with her parents, where she resumes her old job as a lifeguard at the public pool and begins hanging around with high school kids. You can see where this is going… she develops a romantic and sexual relationship with one of the underage teenage boys, which ends tragically when one of his friends commits suicide. Leigh realizes she can’t maintain a relationship with Little Jason and resumes her life in the real world back in the city, though she does receive a postcard from him.

12. Lost in Translation

This is one of those weird plots where you’re not sure if you’re supposed to be rooting for the couple to end up together or not. Bob Harris and Charlotte never actually consummate their relationship (and both of them are married to other people), but you get the feeling that it was always this close to happening, and they get very close very fast as friends. However, if they were really “just friends” why couldn’t they stay in touch? It seems that the only reason they split tearfully at the end of the movie is because they know, due to their own personal circumstances, that they can never truly be together.

11. Drive

Not only is Ryan Gosling tragically beautiful as a broody man of few words, this soundtrack has excellent broody music of few words, too. Driver (literally, Gosling’s character is never named in this film, but he’s a professional stunt driver as well as a criminal driver for hire) falls in love with his neighbor, but unfortunately, her husband gets released from prison and comes between them. Although the husband, as well as other supporting characters, are killed in a crime gone wrong, Driver is able to get away hurt but alive, while his neighbor — and newly unattached widow — knocks longingly on the door to his empty apartment.

10. Dear John

Wow, a Nicholas Sparks story where one of the leading characters actually doesn’t die! Someone dies, because it’s still a Nicholas Sparks story, but it’s neither Sergeant John Tyree nor his lover Savannah Curtis. Instead of death, the leading lad and lady are kept apart by distance and John’s service in the military, and though they exchange letters for years, eventually Savannah marries someone else — until that guy dies, of course. Though John and Savannah run into each other at the end of the movie, there’s no telling whether they actually reunite romantically, even though one of the last things Savannah’s dying husband does is tell John that she still loves him.

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9. Edward Scissorhands

Whose heart doesn’t break just thinking of this movie?! Poor Edward was almost a real boy (sorry couldn’t help it) before his creator suffers a heart attack and dies without affixing his human-like hands, leaving him with blades. I don’t know why anyone, let alone someone with kids at home, would take a stranger with weapons as limbs to their house, regardless of how kind hearted they are, but more power to Peg Boggs I guess. Of course, the neighbors are distrustful and Kim’s boyfriend is jealous, so poor sweet Edward ends up accidentally (mostly) killing the boyfriend and remains a pariah from society, hidden away forever, but even though she never goes back to him, Kim loves him until the end.

8. Liberal Arts

It’s weird seeing Ted Mosby out of MacLaren’s and chasing after a college student instead of “the mother.” Mary Kate and Ashley Olsen’s incredibly talented younger sister plays Zibby, a girl who meets Jesse, a 35-year-old alumni and former student of her father’s, and the two begin an “innocent” pen pal relationship, until Zibby invites him back to visit her and it’s clear that she has more in mind that writing letters. Fortunately, although Jesse clearly has feelings for her as well, he has more sense than to take a 19-year-old’s virginity in her dorm room, so they don’t consummate their passion — though they do make out. The two eventually resume their correspondence, but they don’t stay romantically involved.

7. Casablanca

This classic movie gave us some of the most famous film quotes of all time, including “Here’s looking at you, kid,” “We’ll always have Paris,” and “Of all the gin joints in all the towns in all the world, she walks into mine.” Even though they lived through the stress and drama of war together and continued to love one another even when apart, Rick Blaine and Ilsa Lund do not end up together. Rick saves her life, as well as the life of her husband, whom she stays with. To be fair, Rick essentially pushes her to stay with her husband, but he’s just the tragic romantic hero.

6. My Best Friend’s Wedding

Tale as old as time: girl doesn’t realize she’s actually in love with her male best friend until he gets engaged to another woman. Especially painful when they’re this close to making good on their “if neither of us is married by x age, we’ll marry each other” pact. Especially, especially painful when his fiance is one year older than a teenager and still in college. In Julianne’s case, she actively attempts to sabotage Michael’s engagement to Kimmy instead of just admitting how she feels. She ends up admitting how she feels anyway, after nearly ruining her best friend’s wedding. Everyone comes to their senses and Michael marries Kimmy while Julianne does her best to be happy for them.

5. Tuck Everlasting

The Tuck family has achieved immortality from a spring of youth, so when they’re discovered by the young Winnie, they take her in to keep their secret. Winnie and Jesse fall in love, naturally. So when a con man tries to take Winnie back to return her to her family, the Tucks kill him and get arrested. But fearing that if they are tried to be hanged, everyone will discover they cannot die, they must go on the run until the town forgets all that’s happened. Jesse tells Winnie to drink from the spring so that she’ll stay young, and he’ll come back for her once everything has calmed down.
Except Winnie decides to live her life as it was intended, instead, so when Jesse comes back for her, she’s passed away. (Which is different than death being the reason a couple parts — she made her choice first.)

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4. P.S. I Love You

Yes, obviously Gerry’s character is dead so he can’t be with Holly, but he’s not the only one in love with her. Throughout the movie, as Holly is receiving his romantic letters and reliving their passionate relationship through memories, her friend Daniel is not-so-secretly pining after her. He eventually makes his move, but there is just no spark between the two of them. After all that time of wishing to take it to the next level, they were just not meant to be more than friends. Poor Danny boy. You’ll get the next one, tiger.

3. Sex and the City

Carrie Bradshaw and John James Preston aka Mr. Big aren’t the only couple in this franchise. Many tumultuous years and on-again, off-again phases later, Carrie and Big ultimately end up together in the first Sex and the City movie — even after he initially abandons her at the altar. However, the ever independent Samantha Jones ends it with her movie star boyfriend Smith Jones, using one of the most iconic breakup lines ever: “I love you, but I love me more.” Though she’s an intensely loyal friend, Samantha made it clear through six seasons that she didn’t need a man, and she wasn’t kidding.

2. La La Land

The tale of two ambitious, talented young people in Los Angeles trying to hit it big in show business (that didn’t actually win the Oscar for best picture, whoops!). Although both Mia Dolan and Sebastian Wilder end up pursuing their dreams to success after years of struggling as an actress and musician, respectively, they don’t end up together. Mia becomes a famous actress and Sebastian opens his own jazz club, but Mia is a married woman and mother and there’s nothing left for the two of them but to share a knowing smile as Sebastian plays their old love song.

1. Blue Valentine

Poor Ryan Gosling made the list three times! Where is his happily ever after ending? (Don’t say The Notebook, please). Dean and Cindy meet young, fall in love, get pregnant, and get married — even though Cindy tells Dean the baby might be her ex-boyfriend’s, he still wants to become a family. But nothing stays picture perfect. The couple grows apart, fights all the time, and decides to get divorced, even though they still care for one another. Told through present time and flashbacks, it’s sad seeing how Dean and Cindy were so passionate in the beginning but change toward one another as time goes on.

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