The most romantic day of the year calls for the most romantic movies, so naturally, we’ve put together a lineup that understands love isn’t always candlelit dinners and perfect kisses in the rain. Sometimes it’s messy, funny, complicated – and occasionally, heartbreakingly beautiful.
Mix Hollywood classics, 90s favourites, and modern love stories, and you get romantic movies that don’t just sell the fantasy – they sit with the yearning, the heartbreaks, and the sparks of connection that make it all worth it. Watching with your SO or turning it into a solo, cosy, slightly cheesy night in, here’s what to press play on whenever you’re in the mood.
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The ‘Before’ Trilogy (1995 – 2013)
At last, a romance series exists that treats love like a living thing – changing, deepening, fraying, and surviving – and follows it across nearly two decades without sanding down the rough edges. Richard Linklater’s ‘Before’ trilogy spans ‘Before Sunrise,’ ‘Before Sunset,’ and ‘Before Midnight,’ tracking Jesse (Ethan Hawke) and Céline (Julie Delpy) from a chance meeting on a train in Europe to a reunion years later, and then into the unglamorous, hard-earned reality of staying. What makes it hit is how it keeps evolving – and how your favourite chapter tends to change with you. Either way, if you’ve ever wondered what happens after the credits roll – ten years on, twenty years on – this is cinema’s most honest answer.
In The Mood For Love (2000)
Wong Kar-wai’s ‘In the Mood for Love’ is one of those films that lingers like a sigh you can’t quite shake – all restraint and slow-burning ache, set against the humid hush of 1960s Hong Kong. We follow two neighbours, Chow Mo-wan (Tony Leung) and Su Li-zhen (Maggie Cheung), who begin to notice the same truth: their spouses are having an affair. As they circle the truth, an understanding forms between them – and with it, a connection that’s as intense as it is impossible. What follows isn’t a sweeping romance with declarations and payoff. It’s a dance built on what can’t be said – hallway encounters, shared meals, conversations rehearsed for someone else that slip into something real. Wong directs with a poet’s precision, turning glances and silences into the main event, until longing becomes the loudest thing on screen.
Flipped (2010)
A coming-of-age romance, ‘Flipped’ takes us back to the 1960s, where Juli and Bryce stumble through the awkward, sweet confusion of first love. Juli falls first – wholeheartedly – while Bryce spends most of his time trying to figure out what he’s feeling, and why growing up suddenly makes everything complicated. What lies in store is a story told from both sides, which is exactly why it works. As we flip between their perspectives, the same moments take on new meaning. Directed by Rob Reiner, ‘Flipped’ keeps things refreshingly real – funny, and surprisingly thoughtful about empathy and maturation. And by the time Bryce finally catches up, it’s clear this is one of romance’s simplest laws: she fell first, but he fell harder.
Past Lives (2023)
This is the stunning debut from writer-director Celine Song, and it takes a simple setup – two childhood friends reconnecting years later – and turns it into something shattering. Nora and Hae Sung meet as kids, then life splits them across continents and years, until they find each other again as adults, with all that time sitting between them like a third presence in the room. Like so many of the most affecting love stories, it isn’t driven by big twists. It’s driven by timing: the choices you make because you have to, and the version of love that might have existed if one detail had gone differently. Past Lives is a film about what-ifs, but it’s also about who you become – and the bittersweet ache of meeting someone who brings the person you used to be back into focus.
The Lunchbox (2013)
Another gem that proves romance doesn’t need fireworks, ‘The Lunchbox’ begins with a dabbawala delivery mistake in Mumbai that sends one tiffin to the wrong man. On one end is Saajan (Irrfan Khan), a widower living in the hush of routine. On the other is Ila (Nimrat Kaur), a neglected wife trying to reach her husband through carefully packed meals that keep going unnoticed. What follows is a tender correspondence tucked into lunch carriers – small notes passed back and forth that slowly become a lifeline. As the messages deepen, so does the sense of possibility: not grand declarations, but the courage of admitting you’re lonely, and the comfort of being understood. With warmth and gentle humour, The Lunchbox finds its power in tiny gestures, reminding us that sometimes a wrong turn – an accidental detour – is exactly what takes you where you’re meant to be.
How To Lose A Guy In 10 Days (2003)
Kate Hudson and Matthew McConaughey are peak 2000s rom-com in ‘How to Lose a Guy in 10 Days.’ Hudson plays Andie Anderson, a journalist on assignment to do the impossible: get a man to dump her in ten days, all for a story. Across the table is Benjamin Barry (McConaughey), an ad exec with a wager of his own – that he can make any woman fall for him, fast, to prove he deserves the big campaign. What follows is a glossy push-and-pull of mixed signals and escalating sabotage, with both of them sure they’re the one holding the strings. The twist is that the longer they keep playing, the more real it starts to feel – and once actual affection sneaks in, the ‘rule’ don’t stand a chance.
Portrait Of A Lady On Fire (2019)
‘Portrait Of A Lady On Fire’ is a romance that doesn’t rush – it builds until it feels impossible to look away. Set against an 18th-century coastal landscape of stone houses, cliffs, and sea air, it follows Marianne (Noémie Merlant), a painter hired to create a wedding portrait of Héloïse (Adèle Haenel), a young noblewoman who refuses to sit for it. The catch: Marianne has to study her in secret, memorising her face in stolen moments, then painting by candlelight. What lies in store is a slow shift from observation to intimacy. The more Marianne looks, the more Héloïse looks back – and in that space, desire starts to take shape, charged with everything they can’t say out loud. Céline Sciamma lets glances do the work of dialogue, turning small gestures into entire confessions, until the film becomes less about the portrait and more about the act of truly being seen.
Her (2013)
The near-future world of ‘Her’ looks advanced, but the story it tells is painfully human. Joaquin Phoenix plays Theodore, a lonely writer still bruised by his own life, who buys a new operating system and ends up falling for the voice on the other side – Samantha, brought to life by Scarlett Johansson. Spike Jonze isn’t interested in making it a tech demo. Instead, he uses the futuristic setup to get at something timeless: the need to be seen, to be understood, to have someone meet you where you are. There’s humour running alongside the romance, but the film’s real pull is how intimate and unnerving it can be – a love story about closeness in an age of algorithms, and how connection can feel both easier and stranger than ever. Released in 2013, ‘Her’ hits differently now, less like a ‘what if’ and more like a mirror, reminding you that no matter how modern the world gets, the heart still asks for the same things.
Your Name Engraved Herein (2020)
1980s Taiwan is the backdrop for ‘Your Name Engraved Herein’ – a coming-of-age romance that lives in the gap between what you feel and what you’re allowed to say. Two schoolboys start as friends, then drift into something deeper just as the world around them shifts: martial law has lifted, society is moving forward, and yet the rules around what love can look like still feel brutally fixed. As their connection grows, so does the pressure to perform – to choose survival over honesty, to keep everything contained, to act like it’s nothing. The film is tender, but it never edits out the cost: the compromises, the distance, the way you bury a truth so carefully you almost convince yourself it’s gone. Almost. Because ‘Your Name Engraved Herein’ knows something painfully universal – some feelings don’t fade, even after years spent trying to make them.
50 First Dates (2004)
Romance is in the air – and ‘50 First Dates’ is the reminder that Adam Sandler can do heartfelt just as well as he does comedy. This time, he plays Henry, a guy who meets Lucy (Drew Barrymore) and falls for her fast – an instant, sun-soaked connection that feels like it could change your whole life. There’s just one catch: Lucy has short-term memory loss, which means every morning she wakes up without any memory of the day before – including him. So Henry does the only thing he can do if he wants a real shot at love: he starts again. And again. And again. He finds new ways to introduce himself, new ways to make her laugh, new ways to earn his way into her day – knowing full well it might all disappear by nightfall. It’s warm, funny, and genuinely sweet – a love story that asks what devotion looks like when every day feels like the first.
Eternal Sunshine Of The Spotless Mind (2004)
Every time you rewatch ‘Eternal Sunshine of the Spotless Mind’, it lands harder than you remember. Joel (Jim Carrey), wrecked after his breakup with Clementine (Kate Winslet), signs up for a procedure that promises a clean slate erase her, delete the hurt, move on. But once it begins, his decision flips into something else entirely – a frantic sprint through memories as they cave in around him. Inside those disappearing fragments, Joel keeps running into Clementine again and again, and the nearer he gets to losing her for good, the more fiercely he tries to hold on. What starts as an escape plan becomes the film’s real ache: not whether love is worth it, but what it costs to undo it. Because if you could forget to spare yourself the pain, would you? Or would you choose to remember – knowing it hurt, knowing it changed you – because it made you who you are?
Born in Korea and raised in Hong Kong, Min Ji has combined her degree in anthropology and creative writing with her passion for going on unsolicited tangents as an editor at Friday Club. In between watching an endless amount of movies, she enjoys trying new cocktails and pastas while occasionally snapping a few pictures.
