32 Heartbreaking Movies About Unrequited Love (2025)

It's a tale as old as time, one person's love for another goes unrequited by the other. Sometimes there are societal pressures, sometimes the time just isn't right for one person, and sometimes they just aren't that into the other person. Here is our list of heartbreaking examples of unrequited love in movies.

Past Lives

2023's Past Lives was a gem. The Celine Song written and directed romance story tells the story of two kids living in South Korea who never seem to have the right time to let a romance bloom from their friendship. In the end, the audience is left wondering what could have been, right along with the characters.

Love Actually

There is no better example of unrequited love on film than that scene between Andrew Lincoln and Kiera Knightly in Love Actually. You know the one. After realizing he is in love with Juliet (Knightly), Mark (Lincoln) goes to her door and lays his cards out, literally, in the form of posters with his feelings written out for her to read. She is briefly entranced, but both realize they'll always only be friends.

Casablanca

It's just never the right time for Rick (Humphrey Bogart) and Ilsa (Ingrid Bergman) in Casablanca. It's one of the greatest unrequited love stories ever told on film as these two seemingly soul mates are stuck remembering a magical time that they could never recapture. In the end, they do the right thing, make the correct decisions, and know that they will never be together. They will always have Paris.

(500) Days Of Summer

(500) Days Of Summer is pretty much the classic version of the unrequited love story. Tom (Joseph Gordon-Levitt) and Summer (Zooey Deschanel) start a casual relationship that Summer is completely honest about... at least at first. As Tom falls in love, Summer tries to keep it casual until it all comes to a head and Tom is left brokenhearted.

Rushmore

Wes Anderson's 1998 classic Rushmore is one of the more uncomfortable examples on this list. High school student Max Fischer (Jason Schwartzman) becomes infatuated with a teacher (Olivia Williams) while his classmate Margaret (Sara Tanaka) falls in love with Max. Both are rebuffed by their crushes and it gets messier from there.

Forrest Gump

Forrest Gump (Tom Hanks) is not a smart man. He is a loyal man, though. That loyalty means that from a young age, he is in love with Jenny (Robin Wright). At no point in the many incredible events of his life does he ever fall out of love with his childhood best friend. Jenny, on the other hand, while loyal to Forrest in a way, lives a very different life and rebuffs Forrest throughout it, at least until the very end of her tragic life.

Brokeback Mountain

One of the greatest examples of societal pressures leaving two lovers unable to find the love they crave with each other is Brokeback Mountain. Ennis (Heath Ledger) and Jack (Jake Gyllenhaal) are passionate about each other, but their community would never accept their love, so they are forced to deny it and it creates an absolutely heartbreaking scenario.

The Royal Tenenbaums

We'll admit, that this is one of the weirder, and frankly, more disturbing examples of this list. Richie Tenenbaum (Luke Wilson), you see, is in love with his sister, Margot (Gwyneth Paltrow). It makes for some very uncomfortable moments, to be sure. It's obvious a love that is rightly forbidden. Sometimes you shouldn't root for the couple to get together.

The Great Gatsby

F. Scott Fitzgerald's classic novel The Great Gatsby is the ultimate example of how destructive unrequited love can be. Gatsby, played in the Baz Luhrmann movie by Leonardo DiCaprio, has long regretted asking Daisy (Carey Mulligan) to wait for him. Instead, she marries George (Jason Clarke) and things get very tragic as a result.

Lost in Translation

Bob (Bill Murray) and Charlotte (Scarlett Johannson) are two people stuck in happy marriages who meet in a Tokyo hotel. Though they quickly bond during a night out on the town with each other, things remain pretty awkward. Neither seems to know what to do and as a result, nothing romantic happens. At least until the very end of the movie when they finally share a kiss and leave the end open. So maybe this one works out?

Pretty In Pink

Another classic example of love unreturned is poor Duckie (Jon Cryer) in Pretty In Pink. Duckie will do anything for Andie (Molly Ringwald) and while she is forever grateful for Duckie's loyalty and friendship, she is in love with Blaine (Andrew Shue). Famously, she chooses Blaine at the end, leaving some fans of the movie upset.

Doctor Zhivago

Yuri Zhivago (Omar Sharif) and Lara (Julie Christie) have one of the greatest love stories of all time in the classic Doctor Zhivago. Unfortunately, war and other romantic commitments mean they never have a chance for that "happily ever after).

There's Something About Mary

The thing about Mary (Cameron Diaz) is that everyone is in love with her. It's hard to say whose love is the most unrequited here because there are seemingly dozens of men left in the dust by her in There's Something About Mary. Obviously it finally works out for one of them, Ted (Ben Stiller) but then what about the rest? What about Brett Farve? He did nothing wrong!

Great Expectations (1998)

1998's Great Expectations retells the classic Charles Dickens novel set in modern-day New York City. Finn (Ethan Hawke) falls in love with Estella (Gwyneth Paltrow) but she is evasive and, frankly, mean, about it. She leads him on and uses him to make her fiancee jealous. He never forgets her and eventually, years later, his love is returned.

La La Land

La La Land is a classic example of two people never quite syncing up romantically when they clearly have a passion for each other. For one reason or another throughout the movie, the time never quite works for Seb (Ryan Gosling) and Mia (Emma Stone). They were just destined to be apart.

Les Misérables

Les Misérables includes one of the most famous examples of unrequited love in Western storytelling. Eponine, played by Samantha Barks in the 2012 adaption of the musical, is in love with Marius, but he doesn't return the feelings and as a result, she gives one of the most stirring performances of a song on film with "On My Own."

Roxanne

Steve Martin's underrated comedy Roxanne is loosely based on the famous play Cyrano de Bergerac. Like Cyrano, Martin's character, C.D., has everything going for him, but his unnaturally large nose holds him back from professing his true love for Roxanne (Daryl Hannah).

My Best Friend's Wedding

The title says it all. My Best Friend's Wedding is another classic example of how things happen between two close friends who maybe want more, but never take the leap and realize it's too late when one or the other moves on. It's a hard moment for everyone involved.

Chasing Amy

There are a lot of problematic things in Chasing Amy that we don't need to get into here. Despite those problems, the story is still, at its heart, a story about a man (Ben Affleck) in love with a woman (Joey Lauren Adams) who doesn't reciprocate that love. She has no obligation to, but that doesn't make it less heartbreaking in the end for Affleck's character, Holden.

Once

Missed connections, or bad timing, is the tale told in Once. Two musicians with an obvious connection both artistically and romantically never connect on the latter for a myriad of reasons and though both seem to want it to happen, life and fate keep them apart. It's a sad, and actually somewhat heartwarming story.

To All the Boys I've Loved Before

Lara Jean Covey (Lana Condor) is like almost every high school in some ways. We've all had crushes in high school that go unfulfilled, but Lara takes things to an extreme, writing letters to all the crushes she has, and it's a lot. The letters are never meant to be read by the intended recipient but kept only for her. When the letters get out, things get very messy with love triangles and lots of hurt feelings.

The Remains of the Day

James Stevens and Sally Kenton (Anthony Hopkins and Emma Thompson, respectively) are servants in stately English country estates who have a very complicated relationship that seems like it should be more than it is. Sally is especially in love with James, but he refuses to let her in. There is regret on both sides in the end, though nothing ever comes of their love.

Forgetting Sarah Marshall

Peter Bretter (Jason Segel) just can't get over his ex, Sarah (Kristen Bell). When he finds himself stuck in the same Hawaiian resort as Sarah and her obnoxious new boyfriend, played by Russell Brand, things go from bad to worse. He obsesses over Sarah and is blind to the fact that Rachel (Mila Kunis) is the much better romantic option. Eventually, he realizes the choice is clear.

Edward Scissorhands

Poor Edward (Johnny Depp) in Edward Scissorhands. He never really has a chance to find true love, despite his obvious attraction to Kim (Winona Ryder). She too, reveals her love to him, finally, but both realize it can never happen between them and they part forever.

The Last Of The Mohicans

Like many classic stories of unfulfilled love The Last Of The Mohicans sees Hawkeye (Daniel Day-Lewis) and Cora (Madeleine Stowe) unable to truly be happy together because of the circumstances of their time and place in history. It's not that they don't try, it's that war and society won't allow them to live happily ever after.

West Side Story

There is no more classic example of forbidden love than Shakespeare's Romeo and Juliet. Many versions of Shakespeare's classics have been told on film, and West Side Story is one of the greatest of them all. Two people caught between their love for each other and their loyalty to their gangs find it impossible to be together in one of the most tragic stories ever told.

An Affair to Remember

A tragic missed connection fouls up what could have been an amazing romance between Nickie (Cary Grant) and Terry (Deborah Kerr) in An Affair To Remember. For once, the stars align and it seems two lovers, caught in unhappy relationships, will ditch their partners to be together but fate intervenes tragically and it seems they will never end up happy. Or will they?

He's Just Not That Into You

So, do we really need to explain how this one works? The title alone tells you everything you need to know, right? He's Just Not That Into You is a movie with an all-star cast whose characters are in a lot of messy relationships and there are unrequited feelings all around.

One Day

Dexter (Jim Sturgess) and Emma (Anne Hathaway) spent 20 years flirting with the obvious. They are great friends and at times, each one wants more, but it's never at the same time.

Her

Well, this is one of the weirder ones here, for sure. Her is an unrequited love story about a man, played by Joaquin Phoenix, who is in love with a computer program with the voice of Scarlett Johansson. It's easy to see why things don't work out here, right?

Broadcast News

Broadcast News is an underrated classic from the '80s that despite a myriad of Oscar nominations, seems to be almost forgotten these days. That's too bad because it's a great movie. In the movie, there is a pretty messy love triangle between the three main characters, though none end up together. None of them seem particularly happy about it, either.

Paper Towns

Unrequited high school love is something most people are familiar with and Paper Towns tells a fairly straight forward version of the classic tale of the socially awkward kid in love with the popular kid. Even though it's not the most original of stories, it's told in a great way and is a surprisingly sweet movie.

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