Movies That Only Make Sense If You've Had Your Heart Broken

Heartbreak is a part of life. And yeah, it sucks, no matter your age, or how often you've felt it.

Thankfully, as with most of the best (and worst) things in life, movies are here to comfort us, to wrap us in a warm blanket of stories similar to our own. With cinema, we can find a release, an escape, and an understanding of our own personal experiences. These are my picks for ten movies that only make sense when you're deep in the trenches of a broken heart. 

Chasing Amy

Kevin Smith's subversive rom-com turns twenty years old in 2017, but its central conceit still feels fresh. The idea of a straight man falling in love with a gay woman might seem slightly offensive nowadays, Chasing Amy succeeds primarily thanks to the strength of Smith's writing and the commitment of his two leads.

Ben Affleck plays the conflicted, tormented Holden, a screw-up who manages to mess things up with Alyssa (played by a never-better Joey Lauren Adams) because his feelings are based more on being her first, than having a genuine romantic connection. Adams wisely ensures Alyssa is never seen as a blameless victim, while Affleck makes us empathize with Holden even in his worst moments. 

Smith's main concern, rather than gay-straight gender politics, is what happens when two people just aren't suited to each other, but find themselves attracted, even so.

Heartbreaking moment: The rain-soaked sequence which sees the two finally admit to their feelings for each other is an all-timer, but the moment when Holden immaturely suggests a threesome to fix their relationship, thereby ruining any chances of reconciliation, is pure devastation. 

Manchester by the Sea

The most recent entry on this list, the devastatingly brilliant, Kenneth Lonergan tale of a depressed man and his desperate attempts to reconnect with the life he left behind, following a death in the family, is the epitome of a heartbreak movie. Casey Affleck was rightfully awarded an Oscar for his portrayal of Lee Chandler, who reluctantly returns to the titular town to take care of his nephew.

There is lightness to Lonergan's film, particularly in the interactions between the grumpy Chandler and his teenage charge, but what permeates everything is a sense of unending agony, a hurt that can never be helped. The tragedy at the center of Chandler's unhappiness unravels slowly, finally revealed in an agonizing set piece that lays out, once and for all, why this poor man is the way he is. When Chandler finally reconciles himself to the fact that he can never overcome his past and has to leave again, it is etched with well-judged melancholy and a realistic sense of the inevitability of life. 

Most heartbreaking moment: The scene between Lee and his ex-wife Randi, which sees her try to make amends for their shared past. Worse still, because neither of them come out of it with any sense of reprieve. 

Man Up

A nifty British rom-com, Man Up is one of those boy-meets-girl stories that wrong-foots you at every turn. Although its resolution is a happy one, its central characters both represent different sides of the heartbreak spectrum. With Lake Bell's Nancy, we have a cynical woman who's given up on meeting someone new — to the point she'd rather watch The Silence of the Lambs alone in a hotel room than give her blind date a chance.

On the other side is Simon Pegg's Jack who, following a messy divorce, is set on developing a relationship with a younger woman. Upon meeting, by accident, after Jack mistakes Nancy for his own blind date, the two embark on a night of fun that involves running into his ex-wife and her stalker from high school, among other incidents. Things unravel much sooner than one would expect them to, and the eventual resolution isn't quite as neatly wrapped up as it usually is in these kinds of things (maybe because the script was written by a woman, Tess Morris). The story ends in a hopeful examination of how heartbreak ultimately makes us who we are.

Most heartbreaking moment: Nancy's tear-soaked speech to her family, after she thinks Jack has gone off to be with his actual blind date instead.    

Forgetting Sarah Marshall

Who would leave lovely Jason Segel for Russell Brand? Forgetting Sarah Marshall is another of those subverting-the-usual-clichés rom-coms that paints neither the male nor female participants as the villain (a welcome change). Segel's Peter is on vacation, trying to, as the title of the film suggests, forget about his ex, only to find her in the same resort, holidaying with Brand's loud and proud lothario.

Ostensibly about getting over somebody and falling for someone else, the Segel-written flick's great strength is in revealing Peter's mistakes along the way: from day-drinking, to falling back into bed with Sarah when she shows the slightest hint of regret. Likewise, his new paramour, played by Mila Kunis, isn't as quick to forgive him for his indiscretion as he perhaps expected. Their story is messy, as real-life relationships are.

Most heartbreaking moment: Peter thinks he can get Sarah to stay with him by embracing her while completely naked. Spoiler: it doesn't work. 

Bridget Jones's Diary

Maybe the all-time, go-to girls' heartbreak movie, Bridget Jones's Diary just gets better with age. From the opening, which sees its hapless heroine sadly singing along at the top of her lungs to "All By Myself", to her misadventures with caddish Daniel and dreamy Mark, this is the ultimate in movies to watch when you're nursing a broken heart. It's raw, unflinchingly honest and, at times, quite bleak, particularly when poor Bridge finds herself alone, soon after thinking she was on top of the world.

Helen Fielding's source novel established Bridget as the single girl to whom we could all relate, but Renée Zellweger's fearless performance in the title role of the film adaptation elevated her beyond our collective imagination. A feel-good movie by the end, loaded with laughs and heart, Bridget Jones's Diary is like a collected memoir of all our single girl mishaps that feels quite a bit like hanging out with an old friend who fills up our wine glasses before they've gone empty.

Most heartbreaking moment: When poor Bridget, in her Playboy bunny costume, discovers Daniel's other woman, naked in the bathroom. Adding insult to injury, the woman exclaims "I thought you said she was thin?" Eek. 

Annie Hall

Woody Allen's untouchable rom-com sees Diane Keaton and the director himself bickering, over ninety minutes of lusciously-shot screen-time, as they try to make their doomed romance work. These two don't end up together, which is a relief rather than a hindrance to the movie's message about staying true to yourself and not wasting your life wondering about what could have been.

Keaton's titular character firmly notes that it isn't going to work, leaving Allen's Alvy devastated, but still unable to fully grasp how he's played a role in the demise of their relationship. Allen establishes the central relationship — and eventual break-up — as messy and complicated, because that's how real relationships are. 

Most heartbreaking moment: The final scene between Alvy and Annie, when everything is laid out on the table (quite literally) and it becomes clear that this is it for them. 

Celeste & Jesse Forever

A hugely underrated sort-of rom-com from 2012, Celeste & Jesse Forever is a flick all about what happens when two people really shouldn't (and indeed don't) end up together. Totally believable as ex-husband and wife, and best friends for life, are Andy Samberg and Rashida Jones (who co-wrote the script) whose effortless chemistry powers the whole thing (their inside jokes are a joy, instantly recognizable to anyone in a long-term relationship). 

Over the course of 90 minutes, we watch as they try to figure out their relationship, their ending never quite clear. Celeste & Jesse Forever excels at showing the ins and outs of a long-term relationship, when the romantic love is perhaps gone, but a deep friendship still exists: a connection that neither party is quite ready to give up. Unlike other rom-coms, we're not necessarily rooting for Celeste and Jesse to get (back) together, but to find some way to be in each other's lives without hurting each other. The great beauty of the movie is that, eventually, they do, because they're both trying.

Most heartbreaking moment: Celeste's speech about fighting for what's really important, and how she wishes she had. 

What If

The best will-they/won't-they rom-coms throw a wrench in the works right off the bat, and no modern example does it better than What If: a movie in which the female lead already has a long-term boyfriend when the protagonist meets her (their meet-cute is ground to a halt by this revelation). As played by Zoe Kazan and Daniel Radcliffe, Chandry and Wallace are complicated, realistic characters, both of them battling to figure out what exactly it is that they want.

What If never establishes Chandry as wrong or right, and indeed her partner (Rafe Spall) isn't a thinly-drawn, bad boyfriend character either. He has needs and wants just like she does and they grow apart naturally as she happens to be growing closer to Wallace. Although nothing happens for much of the movie's run-time — they don't even nearly-kiss until the very end — there's a palpable sense of "what if" about their story. It's heartbreaking in its honesty, particularly in Wallace's completely broken character who is hopeful just for a moment, only to be crushed immediately by the mention of the word "boyfriend".

Most heartbreaking moment: When Chandry discovers Wallace has had romantic feelings for her the entire time, and the two argue until she storms off. When they finally kiss is pretty devastating too, in a really lovely way. 

The Crow

There are few films that live better in your memory than in real life, but The Crow, which — despite its infamous reputation (Brandon Lee died on set, among other things) and stunning, comic book visuals — is actually a narrative mess. It rushes from set-piece to set-piece with no real connection between anything, and in spite of being just over 100 minutes in length, feels considerably longer. 

Where it does succeed, however, is in its representation of grief, heartbreak, and loss as seen through its vengeful protagonist, Eric Draven (Lee). The Crow may be a flashy, super-goth revenge movie, but its beginnings lie in the grief experienced by comic book author James O'Barr, after the death of his fiancée at the hands of a drunk driver. O'Barr wrote as a way of coping with the tragedy, and this is felt keenly throughout the source material and the ensuing movie adaptation, even in its wilder moments.

Most heartbreaking moment: Eric's speech to the cop about how nothing is trivial anymore.  


Denis Villeneuve's Arrival is a sci-fi thinker with a twist so heartbreaking it would reduce even the coldest-blooded creature to floods of tears. Adams plays a linguist tasked with communicating with a couple of recently-landed extra terrestrials. For much of the movie, she's a solitary presence, Jeremy Renner fading into the background behind her as we continuously flash back to a devastatingly difficult life she's seemingly already lived.

Except (spoiler alert), what we think are flashbacks are actually flash-forwards. What Adams' character, Dr. Banks, has learned from her new alien friends is how to view time as linear, and as a result, she can re-live moments lost with her now-deceased daughter, as well as Renner, who, it turns out, is/was her husband. This realization dawns on her, simultaneous to the audience, and it's devastating, not least because of its remarkable humanism, a theme throughout the film. 

Most heartbreaking moment: When it becomes clear what choice Dr. Banks has made and why. 

Be the hero of your own love story

Heartbreak is something we all have to contend with at some stage. When it happens to you (or if you're going through it right now, as you read this) try to take solace in the fact that these movies will be there for you, even when nobody else seems to be. They won't judge you for picking the wrong guy, falling out of love, refusing to get out of your pajamas for a week, or for making what feels like the hardest decision of your life.

Get through all ten and you'll definitely feel better, stronger, and ready to take on the world once more — like you're Eric Draven on a revenge crusade, Bridget Jones — single and ready to mingle, or, hell, even Lee Chandler, admitting that something significant needs to change before you can fully move on and rebuild your life.

Trust in the abiding message of all ten films: these characters got through it and so will you.