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Valentine's Day movies through the ages: 10 decades of romantic films

10 of the best love stories from 100 years of cinema

10 February 2025

With Valentine’s Day rapidly approaching (it’s on February 14th, in case you’re panicking), the more cinematically minded among you may start casting your eyes towards the schedule of your local cinema for something appropriately date night-worthy to watch.

Allow us to save you the bother – there’s nothing out there to touch We Live in Time right now for pure lovey dovey content. Florence Pugh and Andrew Garfield play an adorably believable couple exposed to the vagaries of life and love. Bring your tissues.

We Live in Time joins a long and illustrious line of romantic movies dating back to the early days of cinema. For those planning a night in on Valentine’s Day, why not take a spin through the history books and line up one of these classic romantic flicks?

We’ve covered the past 10 decades of cinema here, picking one stand-out romantic movie from each. Some decades have been tougher to whittle down than others (love was clearly in the air during the ’40s, ’60s, and ’10s), but we think we’ve grabbed a reasonably representative spread.

Which of these historical romantic movies is your favourite?


1930s: Gone with the Wind

Gone with the Wind is now viewed as a foundational text for big budget cinema, with its troubled production and enormous box office takings entering into legend. At its heart, however, the film is just a sweeping old romance story. Sure, it’s very much a product of its time, but the story of southern belle Scarlett O’Hara (Vivien Leigh) and her tempestuous relationship with cynical cad Rhett Butler (Clark Gable) is a dysfunctional love story for the ages.

1940s: Brief Encounter

Written by Noël Coward and beautifully shot by David Lean, Brief Encounter’s scandalous (for its time) romance and evocative pre-war setting proved to be hugely influential. It tells the story of two married middle class English people who realise – to their mutual anxiety – that they share an intense attraction. The mannered delivery by the film’s two would-be-adulterers might feel decidedly dated to modern eyes, but it’s still impossible not to be swept along with it all.

1950s: An Affair to Remember

With a snappy script and huge performances from a pair of charismatic leads in Cary Grant and Deborah Kerr, it’s easy to see why An Affair to Remember has become a key reference point for subsequent romantic movies. Our two star-crossed lovers meet on a transatlantic ocean liner to New York, and resolve to meet on the Empire State Building six months later with their affairs duly put in order. Suffice to say, the road to a romantic reunion proves to be a bumpy one.

1960s: The Apartment

Some Like it Hot gets all the headlines, but many hold The Apartment to be the better Billy Wilder film. It’s certainly the more romantic of the two, as we follow Jack Lemon’s downtrodden office drone and his timid pursuit of a heartbroken elevator operator played by Shirley MacLaine. Despite its frothy premise and lightly comic tone, The Apartment is surprisingly unafraid to go to some fairly dark places as our two bruised leads come to confide in one another.

1970s: Annie Hall

Woody Allen’s most lauded film won four Oscars, including for Best Director and Best Actress. The latter in particular was richly deserved, as Diane Keaton established a new kind of female romantic role – smart, quirky, independent, and with a signature dress style that became its own thing. The movie itself is a thoughtful and funny reflection on relationships and mortality, as Allen’s neurotic comedian Alvy reflects on what went wrong with the love of his life.

1980s: When Harry Met Sally

Few romantic comedies have the poise or patience to tell a smart, funny, compelling will-they-won’t-they story over a 12 year time period. But then, few romantic comedies have Nora Ephron writing the script, Rob Reiner directing, and two of the most lovable leads of their generation. We all know the story by now, as the relationship between two New Yorkers (played by Meg Ryan and Billy Crystal) goes from actively hostile to platonic to regretful, before ending up in belated acceptance. Yes, yes, yes, it’s a classic alright.

1990s: Before Sunrise

Richard Linklater’s first in a trilogy of romantic films sees two 20-somethings meeting on a train, then wandering around Vienna talking about love and life all night. It’s hardly a premise to set the pulse racing, but the key to Before Sunrise’s appeal is the cool chemistry between its two leads (played by Ethan Hawke and Julie Delpy) and the gently meandering nature of their conversations. It’s a romantic film very much in the Gen-X mould, though it’s sure to nod to its cinematic forbears along the way. Watching the story continue over the following two sequels is breath-taking stuff, too.

2000s: In the Mood for Love

We don’t know of any other movie couple you’ll be willing to get it on more than Maggie Cheung’s Mrs. Chan and Tony Leung’s Chow Mo-wan. These two handsomely attired neighbours living in a bustling ’60s Hong Kong apartment block discover that their spouses are cheating on them, but their gloomy attempts to nail down how the affair might have progressed leads to a cautious courtship. One of the most beautiful movies ever made, and a real heart breaker.

2010s: Carol

In a decade that turned up a surprising number of high-class romantic movies (La La Land, Her, Portrait of a Lady On Fire, The Big Sick), Carol ultimately won our heart. Todd Haynes’s movie is simply an exquisite piece of film making, expertly conveying the prim window dressing and suffocating social norms of ’50s America. As Cate Blanchett’s glamorous socialite falls for Rooney Mara’s younger shop worker one Christmas, you can practically feel the repressed longing.

2020s: Past Lives

Past Lives is the perfect pick for our current mixed-up decade – especially as a counter-point to the classically weepy We Live in Time. It’s not really a romance movie in the traditional sense, but it is a deeply romantic movie about the complex relationship between two childhood sweethearts. It’s also one of the best films of the 2020s so far, with its beautifully observed insight into the immigrant experience and its wistful reflection on roads not taken.