11 best anti-Valentine’s movies for the romantically unconvinced

Because not every love story deserves a happy ending

Three images sliced together from three different films, left to right: Marriage Story, Deadpool and (500) Days of Summer
(Image credit: Netflix / 20th Century Fox / Searchlight Pictures)

Valentine’s Day films usually follow a very predictable formula: two attractive people meet, something mildly inconvenient happens, then everyone kisses in the rain while a softly strummed indie track plays.

Thankfully, cinema has always had a darker, funnier and far more honest side to relationships, stories about mismatched expectations, brutal breakups, awkward rebounds and the uncomfortable truth that love doesn’t always fix everything. Sometimes it makes things worse. Sometimes it was never really there in the first place.

So if you’d rather watch love unravel than magically fall into place, these are the films that treat romance with a bit more realism, a bit more bite and, crucially, a lot less rose-tinted nonsense that you can enjoy this Valentine's Day.

11. Body Heat

Body Heat (1981) Official Trailer - William Hurt, Kathleen Turner Movie HD - YouTube Body Heat (1981) Official Trailer - William Hurt, Kathleen Turner Movie HD - YouTube
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The film proves that when something looks too good to be true, it probably is. Oh, and it's probably going to get you into truckloads of trouble. William Hurt's naive lawyer finds himself suitably intrigued by Kathleen Turner's husky-voiced femme fatale, and before you can say "they found love in a hopeless place", her husband is dead, he's in jail, and she's on holiday. It's a depressing lesson for us all.

10. Blue Valentine

Blue Valentine (2010) Official Trailer - Michelle Williams, Ryan Gosling Movie HD - YouTube Blue Valentine (2010) Official Trailer - Michelle Williams, Ryan Gosling Movie HD - YouTube
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What's more painful than watching a married couple fall apart? Having it cruelly juxtaposed with how they got together. That's the bittersweet conceit at the heart of this brilliantly played downer. Ryan Gosling and Michelle Williams are the hipster couple who just can't keep it together in this Oscar-nominated indie, which avoids painting either party as "the bad guy", making it all that much harder to endure.

9. Kramer vs. Kramer

Kramer vs. Kramer (1979) Trailer #1 | Movieclips Classic Trailers - YouTube Kramer vs. Kramer (1979) Trailer #1 | Movieclips Classic Trailers - YouTube
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In case you weren't aware, divorce isn't easy and unlike in The War of the Roses, it's also not that funny. Kramer Vs Kramer gave us a more well-measured, gut-wrenching look at what happens when a parent leaves. Dustin Hoffman picks up the pieces when Meryl Streep cuts out in this Oscar-winning feel-bad flick. She comes back and that but it hardly makes for a happy ending. One of the first films to deal with a single father, it was an important 70s drama. Best not watch it if you're considering a family any time soon though.

8. Shame

SHAME: Official HD Trailer - YouTube SHAME: Official HD Trailer - YouTube
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This grim, uncompromising drama presents us with a character who's never celebrated Valentine's Day and probably never will. Unable to form any sort of emotional attachment with women, Michael Fassbender's protagonist focuses on sex, sex and, on weekends, a bit of sex. Presenting the idea some people have childhoods that are so damaging that future relationships seem impossible, it's a chilly alternative to the Hollywood mantra that everyone has a happy ending.

7. Revolutionary Road

Revolutionary Road (2008) Trailer #1 | Movieclips Classic Trailers - YouTube Revolutionary Road (2008) Trailer #1 | Movieclips Classic Trailers - YouTube
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Anyone fooled into thinking this might be a dreamy Titanic reunion will have their hopes ripped apart by this uncompromising drama. Kate and Leo star as a couple whose lofty ambitions are worn down by life in suburbia. As they realise it's all they'll ever have, they start to turn on each other. Helping to confound the downbeat view on marriage, all the surrounding couples in the film are also quietly falling apart. It's also works brilliantly as an excuse to never ever leave the city.

6. Deadpool

Deadpool | Official HD Trailer #1 | 2016 - YouTube Deadpool | Official HD Trailer #1 | 2016 - YouTube
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Deadpool was flat-out marketed as an antidote to Valentine's Day movies on release, complete with mildly mocking love-infused posters. But, of course, it's a violent R-rated irreverent superhero flick that includes "strong bloody violence, strong language and sex references" according to the BBFC. We imagine plenty of couples flocked to watch it on Valentine's Day back in 2016, though, as it's just flat-out a better time than most rom-coms. Deadpool came to cinemas on February 10, 2016, just a few days before Valentine's.

5. Marriage Story

Marriage Story | Official Trailer | Netflix - YouTube Marriage Story | Official Trailer | Netflix - YouTube
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Noah Baumbach's best film is a heart-breaking look at a marriage breaking up - one that has a child caught in the crossfire. You never quite know why the marriage has failed but the cracks are glimpsed throughout. When the movie cranks into cold courtroom drama, it's a devastating watch.

4. Closer

Closer (2004) Official Trailer 1 - Julia Roberts Movie - YouTube Closer (2004) Official Trailer 1 - Julia Roberts Movie - YouTube
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This sharp drama follows the love lives of four flawed Londoners whose attractive exteriors belie a set of coal-like hearts. They take it in turn to lie and cheat their way into and out of each other's beds, leaving you questioning why anyone would want to attempt a relationship in the first place. Julia Roberts and Clive Owen's completely NSFW argument is the high/low point.

3. Fatal Attraction

Fatal Attraction (1987) Trailer #1 | Movieclips Classic Trailers - YouTube Fatal Attraction (1987) Trailer #1 | Movieclips Classic Trailers - YouTube
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While there's surely a counter-argument for this one as it does suggest that cheating will only ever lead to graphic violence, Fatal Attraction is also a terrifying look at what might live behind a seemingly normal face. Michael Douglas learnt to keep it in his pants the hard way as Glenn Close turned his life upside down in this 80s classic. Also makes a solid case for asking all prospective dates for their views on small cuddly bunnies.

2. (500) Days Of Summer

Official Trailer: 500 Days of Summer - YouTube Official Trailer: 500 Days of Summer - YouTube
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If Valentine’s Day sells love as neat, mutual and destined, (500) Days of Summer exists to rip that idea to bits. Told through a fractured timeline, the film follows Tom as he obsessively romanticises his relationship with Summer, ignoring every sign that they’re on completely different pages. What makes it hit is how painfully familiar it feels, the projection, the nostalgia, the way memories edit out the bad stuff. It’s funny, stylish and stacked with charm, but underneath it all is a brutally honest reminder that sometimes relationships don’t fail… they were just never what you thought they were.

1. The War Of The Roses

The War of the Roses (1989) Trailer #1 | Danny DeVito, Kathleen Turner, Michael Douglas, Sean Astin - YouTube The War of the Roses (1989) Trailer #1 | Danny DeVito, Kathleen Turner, Michael Douglas, Sean Astin - YouTube
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Anyone who watched this black comedy in their formative years will have probably grown up with a rather distorted view of marriage. Michael Douglas and Kathleen Turner gleefully tore apart their Romancing the Stone chemistry with this darkly funny look at a divorcing couple fighting to the death over who gets their house. Nastier than most contemporary comedies, it crescendos with a cynically violent climax. Scared of marriage? Us?


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Marc Chacksfield
Content Director

As Content Director of Shortlist, Marc likes nothing more than to compile endless lists of an evening by candlelight. He started out life as a movie writer for numerous (now defunct) magazines and soon found himself online - editing a gaggle of gadget sites, including TechRadar, Digital Camera World and Tom's Guide UK. At Shortlist you'll find him mostly writing about movies and tech, so no change there then.

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