Best Movies for a Broken Heart

One of our favorite Orthogals went through a breakup today, so we’ve written a list of our favorite films for when your heart takes a beating.
Brigid goes for classics where the main characters don’t end up together. Laura favors what fairy tales really end up like. Anna’s on vacation and will get back to you on that.

The characters don’t end up together at the end:

Casablanca – The quintessential loved-and-lost film. Of all the gin joints in all the world…

Roman Holiday – Audrey Hepburn. Gregory Peck. Rome. It’s the perfect combination of funny and bittersweet.

Parapluies de Cherbourg – It’s in French and entirely sung.

Chinatown – Fair warning, this is noir. Politics, murder, incest, corruption. There is no happiness in this ending, but Brigid finds the final line oddly comforting.

The Way We Were – Robert Redford and Barbra Streisand love each other but in the end realize they can’t go on.

My Best Friend’s Wedding – Julia Roberts realizes she’s in love with her best friend…as he announces his engagement.

Life is Beautiful – Mostly about a father and his son surviving a Nazi concentration camp. Watch when you need to cry.

There’s hope for romance in the future:

500 Days of Summer – Boy meets girl. Boy falls in love. Girl doesn’t. Very indie and twee, but oddly touching.

Sliding Doors – Follows two timelines in Gwyneth Paltrow’s life, depending on whether or not she catches the train–and catches her boyfriend cheating.

Under the Tuscan Sun – A woman buys a house in Tuscany with high hopes. Her dreams come true, but not in the way she was thinking it would be.

Gone With the Wind  – You just never know with Scarlett O’Hara.

There is romance in the end:

P.S. I Love You – If you need a good cry. Her husband dies and leaves her notes. There is a happy ending. Also Irish accents.

Definitely Maybe – A man tells his daughter the stories of his 3 great loves.

Sleepless in Seattle – The sleepless widower’s descriptions of love will have you sobbing. In a good way.

He’s Just Not That Into You – Follows the relationships and breakups of an entire social circle.

The First Wives Club – Three divorcées help each other through tough times.

Love Actually – There’s a subplot for everyone in this one, not all of them with happy endings. A solid Christmassy choice.

Sense and Sensibility – Sisterhood, love, honor. They go through a lot to get to those happy endings.

And then when you’re ready, go watch the Princess Bride. It’s going to be okay.


  1. Taisia says

    The Holiday helped me through a breakup. It starts with miserable breakups & ends with romance. It helped me believe I would be able to move on & love again.

  2. says

    I liked The Holiday a lot.
    Last Holiday was also helpful to me, albeit goofy–Queen Latifah gets diagnosed with a terminal illness and decides to break out her bucket list all in one go. I still quote the Swiss chef regularly–the secret to life? Butter.

    The Little Prince, oddly. It helps immensely every time. Hey Anna, let’s do a followup on breakup books, fiction and non.

  3. Bob says

    A movie very few have seen is “A New Leaf” with Walter Matthau & Elaine May. they get married for wrong reasons but eventually it’s right. Hilarious and hard to find.

  4. Kate Barngrover says

    I loved A Good Year with Russell Crowe, Madeline Cotillard, Albert Finney, Romance, Slowing down your life, appreciating good things in your life. Also, Midnight in Paris with Owen Wilson, Rachel McAdams, Kathy Bates,.. Writer is Paris with his fiancé and her parents, he is sitting on the steps and a car comes by filled with famous writers from the past. Romance, love. finding love, unexpected fun.

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