Top 10 Saddest "One That Got Away" Movie Endings

MsMojo

Heartbreak takes center stage as we explore some of the most heartrending romantic tales where love blossoms but fate intervenes. From forbidden passions to impossible choices, these stories capture the bittersweet reality of love that doesn’t last. Join us as we reflect on couples who shared moments of intense connection yet walk separate paths, leaving us with unforgettable emotions and lingering “what-ifs.”

Transcript

00:00Richard! Richard! Richard!

00:05Welcome to Ms. Mojo, and today we're counting down our picks for the most heartbreaking romantic

00:11movies where the couple doesn't end up together. We won't be including romances that don't work

00:17out only because one partner dies. There are spoilers ahead.

00:21Number 10. Anne and Jo. Roman Holiday. It's a tale as old as time. A beautiful princess

00:36sneaks away from her responsibilities for a day, meets an ordinary guy, and falls in love.

00:41Say, hey, you know, you were great back there. You weren't so bad yourself.

00:45Unfortunately for Gregory Peck, there's no genie in this movie to turn him into a prince.

00:54After a day full of adventure and romance, Anne has to return to her royal duties and her home

01:00country, so the two must say goodbye. Promise not to watch me go beyond the corner. Just drive away

01:10and leave me as I leave you. After she walks away, the look on Jo's face says it all. He's hoping

01:18she'll change her mind and come back, but the tears in his eyes tell us that he knows deep down

01:24it won't happen. Their love might have only lasted 24 hours, but it was the real thing.

01:30Number 9. Will and Viola. Shakespeare in Love. This period film revolves around a fictionalized

01:45version of William Shakespeare, who falls in love with an upper-class woman as he's writing

01:50Romeo and Juliet. There is no music in the nightingale. Unless I look on Sylvia in the day,

01:59there is no day for me to look upon. Viola is obsessed with the theatre, and just like Princess

02:06Anne, she sneaks away from her cushy life to spend time with the commoners. However, Viola is already

02:13betrothed to a nobleman, who plans to take her with him when he moves to the New World.

02:18Your children will bear arms, and I will recover my fortune. That is the only matter under discussion

02:22today. You will like Virginia. Virginia. She and Will have spent nearly every day together over the

02:30last several weeks, living in a fantasy that neither wants to leave. But reality soon comes crashing back.

02:36I wanted to be an actor. I'm so sorry, Will. Parting is such sweet sorrow.

02:45Number 8. Guy and Girl. Once. This low-budget Irish musical only had a limited theatrical release

02:53in North America, so it wasn't on many people's radar. There's no flashy costumes or set pieces,

02:59just two musicians who bond over their shared passion.

03:03Falling slowly, eyes that know me, and I can't go back.

03:15They spend a week together playing music and writing songs. Their connection is deeply intimate,

03:20but nothing physical ever happens between them. Eventually, Guy learns that this is because Girl

03:26is married, and she's decided to reconcile with her husband.

03:30Did you write that for your husband?

03:32Yes, I did. And he didn't like it.

03:36Yeah, he's an idiot.

03:37Their parting is less dramatic than most on this list, but that doesn't make it any less

03:42devastating. Their relationship is a classic case of right person, wrong time.

03:47I'll try and make it work. It's for the best.

03:50Number 7. Katie and Hubble. The Way We Were.

03:55It's actually amazing that these two opposites made it work as long as they did.

04:00You're all decadent and disgusting.

04:04Come on. We weren't making fun of you.

04:07Yes, you were. You make fun of everything. You think politics is a joke.

04:11Katie is a strong-willed political activist, while Hubble is happy-go-lucky and popular with

04:17the ladies. They meet at college in the late 1930s, then reunite after Hubble returns from the war.

04:23Their love is strong, but their relationship is rocky because they simply can't overcome their

04:28differences. Look, Katie, I... Oh, God, please don't start a sentence with look. It's always bad news.

04:34I don't think we're going to make it, Katie.

04:36They break up, get back together, and eventually get married. But it doesn't last long.

04:42We're rooting for these crazy kids the whole time, but it's clear they'll both be happier if they

04:47forge their own paths. Your girl is lovely, Hubble. Why don't you bring her for a drink when you come?

04:57I can't come.

04:59Number 6. Mia and Seb. La La Land.

05:02This film takes the typical Hollywood musical happy ending and flips it on its head.

05:07Mia and Seb seem made for each other. They have obvious chemistry and similar struggles in their

05:19careers, and they're both fabulous dancers. In the end, though, they decide to pursue their dreams

05:24separately, rather than try to make things work together.

05:27I don't blame you for that. It's over.

05:31What is? It's over.

05:33What?

05:36All of this.

05:37The final montage, which shows what might have been, is heartbreaking.

05:41They may have made the right choice for themselves and their careers,

05:45but can they truly say they have no regrets?

05:47Success must feel bittersweet when it comes at such a cost.

06:03Number 5. Yuri and Lara. Dr. Zhivago.

06:06Considered to be one of the greatest films ever made, this epic romance follows the titular character,

06:12Yuri Zhivago, through two wars and the Russian Revolution.

06:15My husband.

06:16A lot of courage. He made the rest of us look very feeble. As a matter of fact, I thought you both did.

06:22Good man to shoot at.

06:25I'd give anything never to have met him.

06:27Along the way, he marries Tonya, whom he's known since childhood.

06:31But while he's stationed at a field hospital during World War I,

06:35he meets and falls in love with a nurse named Lara.

06:38If only there were someone to look after you.

06:40But of course, if there were, I'd be destroyed by jealousy.

06:44Zhivago, Tonya.

06:45As the years pass, violence and political upheaval tear Yuri and Lara apart,

06:50then bring them back together, over and over.

06:53Ultimately, Lara is forced to flee Russia for her own safety, while Yuri stays behind.

06:59What shall we do? Can we get on a train?

07:02Now that the rest is on the spot.

07:05I don't want to stay here and wait.

07:08Omar Sharif turns in an understated yet powerful performance as Zhivago,

07:12a man who constantly finds himself at the mercy of forces beyond his control.

07:17Number 4. Chow and Su, In the Mood for Love

07:21Hong Kong director Wong Kar Wai's gorgeous masterpiece tells the story of two neighbors

07:37who discover that their spouses are cheating on them with each other.

07:41While their partners are out of town,

07:43Chow and Su begin spending more time together, and eventually realize they're falling in love.

07:48There are times when I'm thinking, if I haven't been married, I don't know what's going to happen.

07:51Have you ever thought of it?

07:56Maybe I'd rather be happy.

07:58However, they refuse to act on their feelings, believing it would be wrong.

08:02Watching these two pine for each other while only a thin wall and their own sense of decency

08:07separate them is more than just sad.

08:10It's agonizing.

08:11This intimate drama paints a brutally realistic picture of the pain of longing.

08:16Welcome, I'm Zovalki.

08:32Number 3. Marianne and Eloise, Portrait of a Lady on Fire

08:39They know their love is doomed from the start, but the few days they have together are filled

08:53with a passion that they'll probably never know again.

08:56Set in the late 1700s, the film follows Eloise, whose mother is trying to marry her off

09:02to a noble, and Marianne, who has been hired to paint Eloise's portrait.

09:14The two are immediately drawn to each other, but of course, in this time period, a relationship

09:18between two women is impossible.

09:21Watching them discover their true selves together, all while knowing they have no chance at a future,

09:26is gut-wrenching.

09:32Number 2. Rick and Ilsa, Casablanca.

09:41Rick, Blaine, and Ilsa Lund share a brief but intense romance in Paris before circumstances tore them apart.

09:49Their reunion at Rick's nightclub in Casablanca at the height of World War II rekindles that profound connection,

09:55offering the tantalizing possibility of making a life together.

09:59I can't fight it anymore.

10:03I ran away from you once, I can't do it again.

10:05However, Ilsa is married to a heroic resistance leader, whose work is vital to fighting the Nazis.

10:12Eventually, Rick has to make the hardest decision of his life.

10:15Let Ilsa stay with him in Casablanca, or help her escape with her husband.

10:20You already know which he chooses.

10:33Rick makes the ultimate selfless sacrifice, recognizing that the fight for freedom outweighs everything else.

10:40But what about us?

10:42We'll always have Paris.

10:44We didn't have, we lost it until you came to Casablanca.

10:47We got it back last night.

10:49Before we unveil our top pick, here are a few honorable mentions.

10:53Guy and Jean Vievre, the umbrellas of Cherbourg.

10:57Another couple torn apart by war, they're forced to rebuild their lives separately.

11:01Edward and Kim

11:17Romance is especially difficult when one partner has scissors for hands.

11:29I can't.

11:31It was so nice to see you again.

11:43It was a pleasure to see you again, Mrs. Ben.

11:45Goodbye.

11:47Take care.

11:53Gil and Adriana.

11:55Midnight in Paris.

11:57He travels to the past to meet her,

11:59but eventually realizes he belongs in his own time.

12:03So, goodbye, Jim.

12:18Goodbye.

12:19Elio and Oliver call me by your name.

12:22It might be young love, but that doesn't make it any less heartbreaking.

12:26Elio, Elio, Elio, Elio, Elio, Elio, Elio, Elio, Elio, Elio, Elio, Elio.

12:34Olive.

12:37I remember everything.

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12:59Like Marianne and Eloise, Jack and Ennis are kept apart by society's rigid boundaries.

13:06This is a one-shot thing we've got going on here.

13:14There's nobody's business but ours.

13:16They meet while working together in the remote Wyoming wilderness.

13:20Though Ennis is quiet and reserved, their relationship soon turns into a passionate affair.

13:26Jack dreams of getting a place together, but deep down they both know it's all but impossible.

13:31What if you and me had a little ranch somewhere, a little cow and calf operation, be sweet life.

13:39Over the years, they're only able to steal a few fleeting moments together, and they have

13:44to keep them secret at all costs.

13:46If they had been born in a different place or a different time, their story could have

13:51had a much happier ending.

13:53I wish I knew how to quit you.

13:57Then why don't you?

14:01Why don't you just let me be, huh?

14:04Which of these tragic love stories left you in tears?

14:08Let us know in the comments.

14:09When I said I would never leave you.

14:12And you never will.

14:14I've got a job to do too.

14:15Where I'm going, you can't follow.

14:17What I've got to do, you can't be any part of.

14:19What I've got to do, you can't be any part of.

14:20You

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